Hive Novel Discourse

	Main Index Search Register Login Who's Online FAQ Links
	Main Index Search Register Login Who's Online FAQ Links

	1 Online, 0 Active		You are not logged in

This is a historical archiveThe forum is read-only. Private information has been removed. It is not possible to login.

	Novel Discourse	Thread: Forum index Next

All 449 posts Subject: Wanted references Please login to post Down

Rhodium
(Chief Bee)
09-28-01 01:29
No 217986
User Picture       Wanted references

Impurities in illicit amphetamine
Huizer H, Theeuwen AB, Verweij AM, Sinnema A, van der Toorn JM.
J. Forensic. Sci Soc. 21(3), 225-32 (1981)
____ ___ __ _

Isolation, Analysis, and Synthesis of Ephedrine and its Derivatives
Gazaliev, A. N.; Zhurinov, M. Zh.; Fazylov, S. D.; Balitskii, S. N.
Chem.Nat.Compd.(Engl.Transl.), 25(3), 261-271 (1989)

Abstract
A review is given of methods for the isolation, quantitative determination, and modification of the ephedrine alkaloids, and advances in this field of natural compound chemistry.
____ ___ __ _

Seizure And Analysis Of A Clandestine Methylphenidate Laboratory
Abercrombie Jt; Journal Of The Forensic Science Society 28(2), 121-122 (1988)
____ ___ __ _

Analysis Of 1-(3,4-Methylenedioxyphenyl)-1-Ethanamines - Homologs Of 3,4-Methylenedioxyamphetamines
Noggle Ft, Clark Cr, Deruiter J; Journal Of Liquid Chromatography 12 (3): 431-444 1989
____ ___ __ _

[Synthesis of BDB]
Solbach, M.; Guendisch, D.; Wuellner, U.; Blocher, A.; Kovar, K.-A.; Machulla, H.-J.
J.Labelled Compd.Radiopharm. 40, 522-524 (1997)
____ ___ __ _

[N-Methylation by Reduction of N-COOEt Carbamates]
Marshall, F. J. and McMahon, R. E.
J.Labelled Compd.Radiopharm. 6, 261 (1970)
____ ___ __ _

GC-MS identification of amine-solvent condensation products formed during analysis of drugs of abuse
Clark, C R; DeRuiter, J; Noggle, F T, Journal Of Chromatographic Science, 30(10), 399-404 (1992)

Abstract
The use of methanol or ethanol as the injection solvent for the gas chromatographic-mass spectral (GC-MS) analysis of low molecular weight amine drugs of abuse results in the formation of additional components in the sample. Primary amines, such as amphetamine, 3,4-methylenedioxyamphetamine, and phenethylamine, yield imines upon injection as methanol or ethanol solutions. In methanol, the imine formed has a mass that is 12 mass units higher than the parent compound. In ethanol, the products formed have 26 additional mass units. Secondary amines appear to undergo methylation under similar conditions with methanol as the injection solvent. These products are absent from the analysis of equivalent amine samples dissolved in chloroform.
____ ___ __ _

Reaction Byproducts of Common Cold Tablet Ingredients Via Hydriodic Acid/Red Phosphorus
Oulton-S-R; Skinner-H-F, Microgram 32(10), 257-285 (1999)

Abstract
In southern California, the current method of choice for the synthesis of illicit methamphetamine is the reduction of ephedrine or pseudoephedrine with hydriodic acid and red phosphorus. However, as a result of restrictions on the availability of both precursors, common cold tablet preparations are increasingly being used as a source of ephedrine and pseudoephedrine. Such tablets also contain other ingredients such as paracetamol, chlorpheniramine, dextromethorphan, diphenhydramine, doxylamine, guaifenesin, and triprolidine. Depending on the isolation method used, these other compounds may be present in the reaction mixtures and subsequently produce other by-products. This paper describes the by-products formed as a result of the reaction between the tablet ingredients and hydriodic acid/red phosphorus. The identification of the by-products found in clandestine methamphetamine laboratories would help to determine the exact cold preparation used as the source of the precursor.
____ ___ __ _

MS data of some metabolites of the amphetamine derivatives MDA MDMA
Verweij AM, Arch Kriminol. 197(1-2), 27-30 (1996) [Article in German]

Abstract
Mass spectrometric data are presented for the detection of metabolites of the amphetamine derivates 3,4-(Methylenedioxy)amphetamine (MDA) und 3,4-(Methylenedioxy)methylamphetamine (MDMA, Ecstasy) as well as some other derivatives.
____ ___ __ _

Intermediates/byproducts in the illegal production of fentanyl, and its p-fluoro- and N-acetyl analogues
Fritschi G, Klein B., Arch Kriminol. 196(5-6), 149-55 (1995) [Article in German]

Abstract
The aim of the present work was the gaschromatographic and mass spectrometric characterization of intermediates and artifacts in the illegal synthesis of fentanyl and fluorfentanyls. These data provide the means to recognize fentanyls from illicit production.
____ ___ __ _

Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity.
Essawi MYH., Pharmazie 54(4), 307–8 (1999)

Could anyone fetch these two revolutionary articles by Channe Gowda, published back-to back in Ind. J. Chem?

Hydrazine/magnesium mediated cost-effective and selective reduction of nitro compounds
Srinivasa GR, Abiraj K, Gowda DC, Ind. J. Chem. Sect. B, 42(11), 2885-2887 (2003)

Abstract
Hydrazine aided catalytic transfer hydrogenation has been employed for the reduction of both aliphatic and aromatic nitro compounds to corresponding amines. The use of low-cost magnesium, as catalyst leads to high yields of amino compounds under ambient conditions of temperature and pressure. Many commonly encountered functional groups like ethene, nitrile, acid, phenol, halogen etc. are compatible with the present system.
____ ___ __ _

Magnesium/ammonium formate promoted rapid, low-cost and selective reduction of nitro compounds
Srinivasa GR, Abiraj K, Gowda DC, Ind. J. Chem. Sect. B, 42(11), 2882-2884 (2003)

Abstract
The reduction of nitro compounds, both aliphatic and aromatic into corresponding amines has been achieved at room temperature in good yields by employing ammonium formate in the presence of low cost magnesium powder. The hydrogenation is fast and selective in the presence of other sensitive functionalities such as halogens, -OH, -OCH3, -CN, -COOR, -COOH etc. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.
____ ___ __ _

Monohalogenation (bromination and iodination) of electron rich arenes by tetraalkylammonium halides in presence of conc. H2SO4
Pasha M. A., Myint Y. Y., Indian J. Chem., 43B, 357–360 (2004)

Wanted Amphetamine Syntheses:

Preparation of 2-phenylisopropylamine
F.M. Jaeger and J.A. van Dijk
Proc. Acad. Sci. Amsterdam, 44, 26-40 (1941) [CA 37, 6219 (1943)]

Reduction of phenylhydrazone-p-sulfonic acids
R. Fusco and L. Canonica
Chim. Ind. (Milan) 32, 208-210 (1950) [CA 45, 4645a (1951)]

Catalyst selection for the lactonization of 1,4-butanediol
Srinivas B, Subrahmanyam M, Kulkarni SJ, Rao YVS, Rao AVR
Indian Journal Of Chemical Technology 3(4), 237-238 (1996)

Abstract
Chromite catalysts have been studied with and without modifiers for lactonization of 1,4-butanediol. The reaction on majority of the catalyst proceeds giving rise to cyclodehydration product, tetrahydrofuran (THF) mainly rather than cyclodehydrogenation product of gamma-butyrolactone (gamma-BL). The lactonization of 1,4-butanediol increases when the zinc chromite catalyst is modified with Pt metal. Few methods are discussed regarding the preparation and modification of the catalysts and their effects in selectivity from THF to gamma-BL.

Synthetic approaches to cocaine and its analogs
Simoni, Daniele; Rondanin, Riccardo; Roberti, Marinella
Targets in Heterocyclic Systems, Vol. 3, pp. 147-183 (1999)

Abstract
A review of the most important synthetic approaches to cocaine and its analogs with 95 refs. It is presented in the following chapters; (1) Introduction (2) Total synthesis of cocaine via Mannich-type cyclization, nitrone-based approach, and Dieckmann cyclization (3) Synthesis of anhydroecgonine methylester (4) Synthesis of cocaine's analogs (5) Conclusions. Particular attention has been devoted to the recent synthetic acquisitions esp. regarding the synthesis of two-carbon bridge substituted cocaines as well as to conformationally restricted cocaine derivs.
^{(Please scan the pages in an OCR-friendly way, as in completely straight and in 200 DPI. Do not compress with jpg/djvu.)}

Synthesis, Stability and Analysis of MDA analogs
J Alabama Academy Sci 64, 34-48 (1993)

Methadone NMR Analysis
Sci. Pharm. 68(3), 229-234 (2000)

Reactions of aliphatic epoxy compounds. IV. New route for DL-ephedrine synthesis.
Lunge, Jerzy; Belzecki, Czeslaw, Acta Polon. Pharm. 18, 177-81 (1961)

Ref found in in Post 290749 (foxy2: "Novel route to Ephedrine and possibly its analogs", Novel Discourse)

Synthesis of benzyl chloride by solid-liquid phase-transfer catalysis method
Bui Thi Van Nga; Chu Pham Ngoc Son, Tap Chi Hoa Hoc 23(4), 6-7 (1985)

Abstract
PhCH₂Cl was prepd. by chlorination of PhMe with Ca(OCl)₂ using tetrabutylammonium hydrogen sulfate or tetrabutylammonium bromide as phase-transfer catalysts. With suitable ratio of PhMe-catalyst, the yield was high and the reaction was quite selective.
____ ___ __ _

Chemical Reagents 21(5), 264-265 (1999)
Synthesis of 2,5-dimethoxy-4-methylbenzaldehyde (http://www.gallileus.info/gallileus/search/bl_detail?id=RN072969996)

Chemical Reagents 22(6), 356-357 (2000)
A new synthetic method for phenylacetone (http://www.gallileus.info/gallileus/search/bl_detail?id=RN091233939)

Title: Hua hsüeh shih chi = Huaxue shiji = Chemical Reagents
ISSN: 02583283
Homepage: http://huaxsj.periodicals.net.cn/default.html

Libraries in the western hemisphere carrying the journal:
Linda Hall Library (http://www.lindahall.org) (Kansas City, Missouri, USA)
British Library Science Reference Library (http://catalogue.bl.uk/F/9XST3L6151KYSPC6R29HH1UPJJMCR8NHPFP6RPXKGDID7TLA9F-00800?func=full-set-set&set_number=055903&set_entry=000001&format=999) (London, England)
Universitaets Bibliothek und TIB (Hanover, Germany)

foxy2
(Distinctive Doe)
10-02-01 21:11
No 219552
User Picture       Wanted Russian Patent reference

This looks like they have a novel synthesis of P2P, I don't think i have seen this on Rhodiums Page. Sorry if this synthesis has been posted already.

Rodenticidal composition containing indan-1,3-dione derivatives.    Ryl'nikov, V. A.; Polyakov, I. T.; Novikova, A. E.; Yagodovskii, V. V.; Baigusheva, G. A.; Berezovskii, O. I.; Mosin, I. P. (Zakrytoe Aktsionernoe Obshchestvo "Nauchno-Kommercheskaya Firma RET", Russia). Russ. (2000),    No pp. given. CODEN: RUXXE7 C1 20000127 RU 2144766   Patent written in Russian.
Application: RU 99-99102838 19990209. CAN 135:57355 AN 2001:491454

Patent Number: RU 2144766

Abstract

Rodenticidal indan-1,3-dione derivs. are prepd. according to multistage flowsheet. To benzyl cyanide in sodium ethylate medium ethylacetate is added to form phenylacetone, which is then chlorinated with sulfuryl chloride in benzene to give 1-chloro-1- phenylacetone. The latter is reacted with the mixt. of alkylbenzenes (benzene/toluene/ethylbenzene/isopropylbenzene, 1 : 1.2 : 1.4 : 1.6). Mixt. of thus obtained ketones are condensed with di-Me phthalate and to resulting product are added products of regeneration of liq. org. waste from the last synthesis stage. Methylcellulose, sodium CM-cellulose, vegetable oil and others can be used as fillers. Rodenticide may also contain attractant, dye, water, and preservatives, and can be used for prepn. of rodenticidal baits.

Do Your Part To Win The War

Acme
(Hive Bee)
10-08-01 03:18
No 221493
User Picture       Post deleted by Rhodium

Rhodium
(Chief Bee)
10-08-01 10:32
No 221613
      Post deleted by Rhodium

psychokitty
(Hive Bee)
10-19-01 03:40
No 226622
User Picture       Re: Wanted Russian Patent reference

Isomerization of pseudoephedrine into ephedrine...
Izv. Akad. Nauk Kaz. SSR, Ser. Tekhn. i Khim. Nauk 1963 (3), 20-7 (pub. 1964) (Russ); cf Tr. Inst. Khim. Nauk, akad. Nauk Kaz. SSR 4, 127-34 (1959).

Reference retrieved and can be read at Post 425116 (Flogiston: "Изомеризация псевдоэфедрина в эфедрин.", Russian HyperLab)

Edit: "Chem. Abs. Vol 2, 3348 has something about isomerizing ephedrine and pseudoephedrine into the other isomer (in equilibrium) using HCl." /PolytheneSam

foxy2
(Distinctive Doe)
11-02-01 05:27
No 231943
User Picture       Re: Wanted references

Anyone Near Purdue??
If you are check this dissertation?

Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine.
Blair, Joseph Bernard.
Purdue Univ., West Lafayette, IN, USA. Avail. UMI, Order No. DA9818919. (1997),    124 pp.
From: Diss. Abstr. Int., B 1998, 58(12), 6592.
Dissertation written in English.
Do Your Part To Win The War

Rhodium
(Chief Bee)
11-23-01 11:10
No 239660
User Picture       Re: Wanted references

Method with Benzyl Chloride and sodium give benzyl sodium. This is reacted with ethyl acetate to give phenylacetone.

Tsuruta, Bull. Inst. Chem. Research, Kyoto Univ., vol. 31, 190-200 (1953) (in English); Chemical Abstracts vol 49, 6183b

muriatic_asshole
(Hive Addict)
11-25-01 15:39
No 240336
User Picture       Post deleted by Rhodium

Rhodium
(Chief Bee)
11-26-01 21:28
No 240898
      Post deleted by Rhodium

Sonson
(Stranger / Eraser)
11-27-01 12:27
No 241229
User Picture       Re: Wanted references

Bromination of 1,4-dimethoxybenzene to 2-bromo-1,4-dimethoxybenzene followed by chloromethylation to 4-bromo-2,5-dimethoxybenzyl chloride.

I've read this one...nothing new I'm afraid...there's one in J. Prakt Chem i think were they use 4-Me instead thats pretty good because they use paraformaldehyd instead of formaldehyde and dont gas the mix with HCl...I'll get them for you..

Lilienthal
(Moderator)
11-27-01 15:15
No 241251
User Picture       Re: Wanted references

Foxy, data from that dissertation about fluorinated tryptamines and thienopyrrolee has been published in J. Med. Chem. in two different papers a while ago. Search for the co-author D. E. Nichols. But both papers didn't look very promising. The fluorinated tryptamines were 5-HT1A selective if I remember correctly.

Rhodium
(Chief Bee)
11-27-01 17:00
No 241276
User Picture       Re: Wanted references

S. N. Danilov, Zhur. Obschei. Khim (J Gen Chem) 18, 2000-2007 (1948)
Chem. Abs. 4632 (1949)

Review of H2SO4 and Hg²⁺ catalyzed isomerization of aldehydes to ketones (including phenyl-2-propanal to P2P, as in https://www.rhodium.ws/chemistry/p2p.2pp.html ).

Rhodium
(Chief Bee)
12-01-01 21:55
No 243097
User Picture       Post deleted by Rhodium

Rhodium
(Chief Bee)
12-02-01 17:29
No 243298
      Re: Wanted references

"Electrochemical study of nitrostyrene derivatives: steric and electronic effects on its electroreduction"
This reference retrieved by lugh, thanks!

foxy2
(Distinctive Doe)
12-02-01 23:36
No 243377
User Picture       Re: Wanted Russian Patent reference

Can someone find the patent listed on this page?
Its about making asarone-free calamus oil.

http://www.tifac.org.in/offer/tsw/ihbt5.htm

Do Your Part To Win The War

PolytheneSam
(Master Searcher)
12-02-01 23:54
No 243381
User Picture       Re: Wanted Russian Patent reference

Patenting Details: A patent on asarone free oil has been filed in USA (patent No. 09/652,376 filed on Aug. 31, 2000)

That looks like a patent application. They publish them after 18 months now. 09/652,376 is an application number not a patent number. Maybe it'll bee published in January.

http://www.geocities.com/dritte123/PSPF.html

psychokitty
(Hive Bee)
12-06-01 03:39
No 244764
User Picture       Post deleted by Rhodium

Rhodium
(Chief Bee)
12-07-01 23:47
No 245440
      Post deleted by Rhodium

Rhodium
(Chief Bee)
12-08-01 18:28
No 245643
User Picture       Post deleted by Rhodium

UTFSE
(Hive Bee)
12-08-01 23:56
No 245712
      Re: Wanted references

preparation of 3,4-dihydroxy-5-methylbenzaldehyde

I found this - hope it helps.

us3410903 preparation of aliphatic oxides
us3387036 production of benzyl alcohol and bezaldehyde
us3799940 process for producing aromatic aldehydes
us3658875 process for preparing aromatic aldehydes and    the corresponding alcohols
us 3975309 2,4-dihydroxy-3-methyl-benzaldehyde perfume compositions
just glad to bee here-----he he he

Rhodium
(Chief Bee)
12-11-01 12:32
No 246433
User Picture       Post deleted by Rhodium

uemura
(Hive Bee)
12-15-01 13:43
No 247827
      Re: Wanted references

With respect to the epoxidation of olefins, Uemura found the following ref:

Iron-Cyclam Complexes as Catalysts for the Epoxidation of Olefins by 30% Aqueous Hydrogen Peroxide in Acetonitrile and Methanol.
J. Am. Chem. Soc., 1991, 113, 7052-7054.

Rhodium
(Chief Bee)
12-18-01 09:52
No 248668
User Picture       Re: Wanted references

Peracid oxidation of indene, styrene, allylbenzene, propenylbenzene and other interesting compounds.
Now we might find the product of peracid oxidation of safrole, to see if there is a good way from there to MDP2P!

Stuurman, Proc. Acad. Sci. Amsterdam, 38, 450 (1935)

Rhodium
(Chief Bee)
12-28-01 17:58
No 250968
User Picture       Re: Wanted references

Good info on dillapiole and related compounds:
Improvements in or relating to methylenedioxyphenyl derivatives,
Indian Patent No. 128, 129 (1969)

A. W. K. DeJong, l-Cocaine from l-Ecgonine,
Rec. Trav. Chim. Pays-Bas 59, 27 (1940), and with the following abstract in english: CA 2386 (1940)

PolytheneSam
(Master Searcher)
02-13-02 23:16
No 269315
User Picture       Re: Wanted Russian Patent reference

I wonder if the Russian application is patented or published yet.
http://www.geocities.com/dritte123/PSPF.html

element109
(Hive Bee)
04-11-02 15:10
No 295499
      much improved Duff ref.

Does someone has access to the journal "Chemistry Express"?
I believe it's Japanese but written in English

CAN 114:184910 describes the improved Duff reaction with ArOH, Ac2O and hexamine ---> HOArCHO, yields exceeding 70% !

it's CHEM. EXPRESS (1991), 6(1), p37-40

e109

Lino
(Hive Bee)
04-11-02 18:42
No 295568
User Picture       New synthetic method for phenylacetone

This sounds fairly interesting if anyone can access this title. Found it using 'Chemspy'

Title A new synthetic method for phenylacetone
Author/s Kefen, Y., Zhen, S., Dongsheng, L., Tao, L.
Source CHEMICAL REAGENTS ,   22(6):356-357 2000
Service Fee: $10.75   ;   Copyright Royalties: Unknown
ISSN 02583283
Publisher CHEMICAL REAGENTS
Classification Natural sciences & mathematics / Chemistry & allied sciences / Analytical chemistry

Linoleum: the 13th element! Now available at all good DIY stores… & Walmart.

Antoncho
(Official Hive Translator)
05-29-02 08:02
No 315549
User Picture       Post deleted by Rhodium

Antoncho
(Official Hive Translator)
06-08-02 08:20
No 318800
      This could bee regarded as crossposting, but ...

This could bee regarded as crossposting, but please don't blame me for that - i figured that Post 318797 (Antoncho: "Another interesting and easy formylation", Novel Discourse) (where this is discussed in detail) is quite long and not many a bee will care to read it till the end smile

The ref is about making triethyl ortoformate from OTC ingredients, it's also old and German:

Walter, J. prakt. Chem. (2) 48, 231 (1893)

Please,

Antoncho

Rhodium
(Chief Bee)
06-15-02 09:14
No 321595
User Picture       Mescaline synthesis review

Review of repoerted synthetic routes to Mescaline and other phenethylamines
Progress in Drug Research vol 11, pp 11-47, Birkhauser Verlag, Basel (1968)

Rhodium
(Chief Bee)
08-05-02 19:26
No 341761
User Picture       Recent Synthetic Applications of Chiral ...

Recent Synthetic Applications of Chiral Aziridines
Synthesis 1347-1365 (2000)

Due to their ready availability in chiral form, and propensity to undergo regio- and stereoselective ring opening, aziridines have found widespread use in asymmetric synthesis. This review attempts to summarise the breadth of use of chiral aziridines in synthesis that has recently been reported. Particular emphasis is put on the effect of substituents on ring openings, rearrangements and use as chiral ligands and auxiliaries.

http://www.thieme-connect.de/DOI/DOI?10.1055/s-2000-7097 <- Please get this in PDF format for me!

Flip
(Hive Bee)
08-06-02 10:12
No 342045
User Picture       My Bare Essentials

Please forgive this rather tall order. Most of these are quite common, but I have no books of my own and no access to this media other than the bits and peices I can scrap up through web searches. And I am working on a big project.

If you know what I am working on you will understand why I need these, and if you examine the organization of my list based on the contents of the articles you will realize that I put ALOT of thought into this. So please help wherever you can help, preferably by PM. It will be extremely appreciated.

P. S. Bailey, Ozonation in Organic Chemistry; Academic Press, New York, vol 1, 1978; vol 2, 1982

P. S. Bailey, J. Org. Chem., 22, 1548 (1957); Ind. Eng. Chem., 60, 993 (1958)

I. J. Solomon, K. Hattori, A. J. Kacmarek, G. RI. Plata, and M.J Klein, J. Am. Chem. Soc., 84, 34 (1962)

D. Seebach D. Enders, Angew. Chem. Int. Ed. Engl. 14, 15 (1975)

D. Seebach E. W. Colvin, F. Lehr, T. Weller, Chimia 33, 1 (1979)

R. Criegee and G . Lohaus. Ann., 688, 6 (1953); Chem. Ber., 86, l (1953)

R. Criegee, G. Blust, and H. Zincke, Chem. Bel., 87, 7G6 (1954)

R. Criegee, A. Kerckow, H. Zinke, Chem. Ber. 1955, 88, 1878-1888

R. Criegee, Angew. Chem. 1975, 87, 7652771; Angew. Chem Int. Ed. Engl. 1975, 14, 7452752.

Großmann, D., Ph.D.thesis (1999) Joh. Gutenberg Univ. Mainz

Harries, Ann. 343, 311 (1905)

Neeb,P., G.K. Moortgat, J. Phys. Chem. A, 103, 9003-9012 (1999)

Bauerle, S., and G.K. Moortgat, Chem. Phys. Let., 309, 43-48 (1999)

Diaper, D.G.M.; Mitchell, D.L. Can. J. Chem., 1962, 40, 1189

R. G. Ackman, AI. E. Reston, L. R. Gallay, and F. A. Vandenheuvel, Can. J. Chem., 39, 1956 (1961)

C . C. Schubert and R. N. Pease, abid., 78, 2044, 55.53 (1956)

P. Bailey, Chem. Re?., 68, 984 (1958)

There are more....... god there are so many more. Rest assured these were selected from a much longer list as being fundamental. I need to find some cheap way of getting a database account. I promise I will not make a habit of this.

Thank you above and beyond all thanks,

Flip

"Holy shit, would you look at that?" - Flip (8/4/2002)

Rhodium
(Chief Bee)
09-19-02 14:05
No 358103
User Picture       Urushibara Ni Catalysts

The references below was gotten from Post 279529 (PolytheneSam: "Re: New tidbits on urushibara", Chemistry Discourse):

CA Vol. 95, 1981 95:96939y and 95:96940s

   95:96939y Optimization of Urushibara nickel catalysts for hydrogenation. Part I. Effect of preparation conditions on the spectific activity of the catalyst. Maksimova, N. A. ; Fasman, A. B. (Inst. Org. Katal. Elektrokhim., Alma-Acta, USSR). Izv. Akad. Nauk Kaz. SSR, Ser. Khim. 1981, (3), 26-31 (Russ). A math. model was derived to describe the activity of Urushibara Ni catalysts in hydrogenation of HC÷CCMe2OH as a function of the prepn. conditions. Improved catalysts were obtained by increasing the Zn content, the concn. of the HCl used to treat the Zn before the onset of cementation, and the cementation temp., and by decreasing the Al content and AcOH concn.

   95:96940s Optimization of Urushibara-type nickel catalysts for hydrogenation. Part II. Effects of preparation conditions on the selectivity of hydrogenation of dimethylethynylcarbinol. Fasman, A. B.; Maksimova, N. A.; Pel'menshtein, B. Ya. (Inst. Org. Katal. Elektrokhim., Alma-Acta, USSR). Izv. Akad. Nauk Kaz. SSR, Ser. Khim. 1981, (3), 31-4 (Russ).
A simplified math. model was derived to describe the effects of the conditions of the prepn. of Urushibara Ni catalysts on the selectivity of HC÷CCMe2OH hydrogenation with them. The max. selectivity for CH2CHCMe2OH was 93% , obtained using 20% Pd2+, 40% Mn2+ and 1:10 (Ni, Pd, Mn)/Al at pH 6.5, cementation at 40º for 30 min, leaching at 40º with 20% NaOH for 20 min, Al particle size 0.2-0.4 mm, and wash-water temp. 20º.

Rhodium
(Chief Bee)
09-20-02 13:57
No 358507
User Picture       Misc Indian Journal of Chemistry

Indian journal of chemistry. Section B, Organic including medicinal, 41(5):1072-1074 (2002)
Reduction of oximes with sodium borohydride - copper (II) sulfate in methanol

Indian journal of chemistry. Section B, Organic including medicinal, 41(5):1064-1067 (2002)
Removal of commonly used protecting groups by catalytic transfer hydrogenation with formic acid and 10% Pd/C

J.Appl.Chem.USSR (Engl.Transl.), 47, 2840-2841 (1974)
Zh.Prikl.Khim. (Leningrad), 47, 2751 (1974)
A supposedly very interesting article (both are the same in russian/english) on the epoxidation of Isosafrole, by Baranova et al.

Journal of Physical Chemistry (USSR) 24, 745-59 (1950)
Electrochemical reduction of nitromethane to methylamine performed in aqueous HCl, essentially producing an aqueous methylamine hydrochloride solution from racing fuel and some stray electrons.

Sodium Aluminum Hydride
Zakharkin et.al., Izv. Akad. Nauk SSSR Ser. Khim., 561 (1964)
Reductions using the cheap LAH analog NaAlH₄ in hydrocarbon solvents.

The Synthesis of ¹⁴C-diethylamine and lysergic acid diethylamide
Journal of Labelled Compounds and Radiopharmaceuticals 10:(2), 207 (1974)

Sodium borohydride-iodine, an efficient reagent for reductive amination of aromatic aldehydes
Indian Journal of Chemistry Sect. B, 41(9), 1970-1971 (2002)

Synthesis of 3,4-methylenedioxyphenyl-2-propanone
Jingxi Huagong, 18(6), 321-324 (2001)
Jingxi Huagong Bianjibu [In Chinese]. CODEN: JIHUFJ. ISSN: 1003-5214.
Xiao, Guo-min; Gu, Hai-ming; Zhang, Jin
(Department of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, Peop. Rep. China).
DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology))

A process for the prepn. of (3,4-methylenedioxyphenyl)-2-propanone was studied by means of epoxidn. of safrole and subsequent catalytic isomerization of the so-obtained epoxide. (3,4-Methylenedioxyphenyl)-2-propanone is a useful intermediate for the synthesis of methyldopa, an important antihypertensive agent. The optimal result was obtained by expts. done under various conditions, such as kind of catalyst, consumption of catalyst and reaction time. The yield of epoxidn. achieved 92% at n(catalyst):n(safrole) = 0.0039, n(catalyst):n(H2O2) = 0.0046, n(H2O2):n(safrole) = 0.87, reaction time 4 h, reaction temp.356-358K and with 1,2-dichloroethane as solvent. The yield of isomerization achieved 91% at n(LiI):n(crude product) = 0.045, reaction time 6 h, reaction temp. 351-353 K, with Et acetate as solvent and LiI as catalyst. Purity of the title compd. was over 95%.

Rhodium
(Chief Bee)
11-09-02 22:54
No 378180
User Picture       Sodium Aluminum Hydride

Sodium Aluminum Hydride
Zakharkin et.al., Izv. Akad. Nauk SSSR Ser. Khim., 561 (1964)
Reductions using the cheap LAH analog NaAlH₄ in hydrocarbon solvents.

Clandestine drug synthesis
Medicinal Research Reviews - Volume 6, Issue 1, January - March 1986, Pages 41-74
Soine, W H {Journal Article, Review; 242 References}

Rhodium
(Chief Bee)
11-29-02 00:17
No 384430
User Picture       Synthesis of 3,4-methylenedioxyphenyl-2-propanone

Jingxi Huagong, 18(6), 321-324 (2001)
Jingxi Huagong Bianjibu [In Chinese]. CODEN: JIHUFJ. ISSN: 1003-5214.
Xiao, Guo-min; Gu, Hai-ming; Zhang, Jin
(Department of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, Peop. Rep. China).
DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology))

A process for the prepn. of (3,4-methylenedioxyphenyl)-2-propanone was studied by means of epoxidn. of safrole and subsequent catalytic isomerization of the so-obtained epoxide. (3,4-Methylenedioxyphenyl)-2-propanone is a useful intermediate for the synthesis of methyldopa, an important antihypertensive agent. The optimal result was obtained by expts. done under various conditions, such as kind of catalyst, consumption of catalyst and reaction time. The yield of epoxidn. achieved 92% at n(catalyst):n(safrole) = 0.0039, n(catalyst):n(H2O2) = 0.0046, n(H2O2):n(safrole) = 0.87, reaction time 4 h, reaction temp.356-358K and with 1,2-dichloroethane as solvent. The yield of isomerization achieved 91% at n(LiI):n(crude product) = 0.045, reaction time 6 h, reaction temp. 351-353 K, with Et acetate as solvent and LiI as catalyst. Purity of the title compd. was over 95%.

Rhodium
(Chief Bee)
11-30-02 06:32
No 384831
User Picture       Ketone deoxygenation with NaBH4?

In JOC 48, 4151 (1983), the following procedure is described:

"Thus, 2-hydroxy-3-Bromo-5-methoxybutyrophenone was first acetylated (5 eqv Ac2O/5 equiv 5% NaOH/ice/3 min) and then the crude acetate was treated with 4 eqv of NaBH4 (aqueous THF/15°C/1 h) to furnish 2-hydroxy-3-Bromo-5-methoxybutylbenzene in 92% yield."

The reference they give is Minami & Kijima, Chem. Pharm. Bull. 27, 816-820 and 1490-1494 (1979)

I have never before seen such a mild ketone deoxygenation, so I'm really curious what the original article says.

Rhodium
(Chief Bee)
12-11-02 17:55
No 388445
User Picture       Asian Journals

Chemical Reagents 21(4), 231-232 (1999) Synthesis of 1-(2-bromophenyl)-2-propanol
Chemical Reagents 21(5), 264-265 (1999) Synthesis of 2,5-dimethoxy-4-methylbenzaldehyde
Chemical Reagents 22(6), 356-357 (2000) A new synthetic method for phenylacetone

Publication ISSN: 02583283
Homepage: http://huaxsj.periodicals.net.cn/default.html

Libraries in the western hemisphere carrying the journal:
Linda Hall Library (Kansas City, Missouri, USA)
British Library Science Reference Library (London, England)
Universitaets Bibliothek und TIB (Hanover, Germany)

http://www.lindahall.org/

Title Hua hsüeh shih chi = Huaxue shiji.
LHL shelved as Huaxue shiji.
Publisher Pei-ching : Hua kung pu hua hsüeh shih chi k‘o chi ch‘ing pao chung hsin chan, 1979-
Description v. : ill. ; 26 cm.
Notes Title from cover.
In Chinese; added contents and summaries in English.
Citation Chemical abstracts
Local note Library copy of vol. 5, no. 2 lacks p. 89-104.
Frequency Bimonthly
Subjects Chemical tests and reagents -- Periodicals.
Add author Hua kung pu hua hsüeh shih chi k‘o chi ch‘ing pao chung hsin chan (China)
Add title Huàxué shìjì
Huàxué shìjì
Huaxue shiji
Chemical reagents 1981-
Coden HUSHDR
ISSN 0258-3283
LCCN 90645632 /ACN
sn 86011321
Holdings
Serial Copy:
Location Collection Call No. Copy # Media type PAC Display Note
Linda Hall Library - Closed Stacks Serials - LHL serial Annual index in last issue of year.
Main run v5(1983)--18(1996);
Main run Vol. 19-20 no. 1-6 February 1997-December 1998
Main run Vol. 26 no. 1 1998
Main run Vol. 21 no. 1-6 February 1999 - Dec. 28, 1999
Main run Vol. 22 no. 1-5 February-October 2000
Main run Vol. 23 no. 1-6 February-December 2001
Main run Vol. 24 no. 1-3 February-June 2002

java
(Hive Bee)
12-11-02 21:38
No 388527
User Picture       Re;Chemical Reactions

http://www.lindahall.org/

Title Hua hsüeh shih chi = Huaxue shiji.
LHL shelved as Huaxue shiji.
Publisher Pei-ching : Hua kung pu hua hsüeh shih chi k‘o chi ch‘ing pao chung hsin chan, 1979-
Description v. : ill. ; 26 cm.
Notes Title from cover.
In Chinese; added contents and summaries in English.
Citation Chemical abstracts
Local note Library copy of vol. 5, no. 2 lacks p. 89-104.
Frequency Bimonthly
Subjects Chemical tests and reagents -- Periodicals.
Add author Hua kung pu hua hsüeh shih chi k‘o chi ch‘ing pao chung hsin chan (China)
Add title Huàxué shìjì
Huàxué shìjì
Huaxue shiji
Chemical reagents 1981-
Coden HUSHDR
ISSN 0258-3283
LCCN 90645632 /ACN
sn 86011321
Holdings
Serial Copy:
Location Collection Call No. Copy # Media type PAC Display Note
Linda Hall Library - Closed Stacks Serials - LHL serial Annual index in last issue of year.
Main run v5(1983)--18(1996);
Main run Vol. 19-20 no. 1-6 February 1997-December 1998
Main run Vol. 26 no. 1 1998
Main run Vol. 21 no. 1-6 February 1999 - Dec. 28, 1999
Main run Vol. 22 no. 1-5 February-October 2000
Main run Vol. 23 no. 1-6 February-December 2001
Main run Vol. 24 no. 1-3 February-June 2002

Chimimanie
(Newbee)
12-24-02 16:03
No 392439
User Picture       potassium tert-butoxide

I don't have much hope in acquiring them but anyway if somebee can help:

Production of potassium tert-butoxide by azeotropic distillation with reaction.    Wang, Huachun; Guo, Guangyuan; Li, Fusheng; Liu, Bangfu; Tan, Qiu.   Res. Development Cent. Petrochemical Technol., Tianjin Univ., Tianjin, Peop. Rep. China. Shiyou Huagong (1997), 26(11), 761-763. CODEN: SHHUE8 ISSN: 1000-8144. Journal written in Chinese. CAN 128:24233 AN 1997:770244   CAPLUS
Abstract
The reaction of producing potassium tert-butoxide (I) from potash and tert-Bu alc. is an intensive reversible reaction. Because the reaction equil. favors the formation of alc., I cannot be obtained without removing the water formed during the reaction. So a technol. integrating azeotropic reaction distn. in boundary film and a packed column having large surface area is applied. The potash conversion is greater than 93%. It has obvious tech., economical and safety advantages over the traditional method of producing I from metallic K.

Technology, apparatus, and magnification of producing potassium tert-butoxide by azeotropic distn. reactive distillation.    Wang, Huachun; Guo, Guangyuan; Li, Fusheng; Liu, Bangfu; Tan, Qiu. Researching and Development Center for Petrochemical Technology, Tianjin University, Tianjin, Peop. Rep. China. Huaxue Gongcheng (Xi'an, People's Republic of China) (1998), 26(3), 45-48. CODEN: HUGOEN ISSN: 1005-9954. Journal written in Chinese. CAN 130:26600 AN 1998:707632 CAPLUS
Abstract
A technol. integrating azeotropic reactive distn. and a packed column with big surface area were used for prepg. potassium tert-butoxide from KOH. The structure of the packed column, the actions of wave filler, distributor, redistributor, and multiple step filler, process chart, and technol. conditions are introduced. The rate of KOH conversion was > 93%.

Antoncho
(Official Hive Translator)
12-27-02 11:41
No 393252
User Picture       4-Hydroxyindole

This discussion has been moved to Post 393684 (Rhodium: "4-Hydroxyindole Synthesis", Tryptamine Chemistry). /Rhodium

Antoncho
(Official Hive Translator)
12-28-02 17:00
No 393507
      Another reduction of PEAs

G. Hahn, K. Stichl (sp?) Ber. (Berichte?), 71, 2154 (1938)

Hydrogenation of w-nitrostyroles to PEAs.

Antoncho

Kinetic
(Hive Bee)
01-02-03 18:01
No 394870
      Methylenedioxypropiophenone

It seems my library doesn't carry this Journal after all. Details the acylation of benzodioxole in 58% yield, the 'abstract' below originally came from Post 361935 (Rhodium: "Everything you need for methylone.", Novel Discourse):

Reaction 16 of 34
Reaction ID 1651712
Reactant BRN 115506 benzo[1,3]dioxole
385632 propionyl chloride
Product BRN 165729 1-benzo[1,3]dioxol-5-yl-propan-1-one
No. of Reaction Details 1
Reaction Classification Preparation
Yield 58 percent (BRN=165729)
Reagent SnCl4
Solvent CH2Cl2
Time 1 hour(s)
Temperature 20 C
Ref. 1 5702207; Journal; Daukshas, V. K.; Gaidyalis, P. G.; Pyatrauskas, O. Yu.; Udrenaite, E. B.; Gasperavichene, G. A.; Raguotene, N. V.; PCJOAU; Pharm.Chem.J.(Engl.Transl.); EN; 21; 5; 1987; 341-345; KHFZAN; Khim.Farm.Zh.; RU; 21; 5; 1987; 569-573.

'Pharm.Chem.J.' being an abbreviation of 'Pharmaceutical Chemistry Journal' smile

Rhodium
(Chief Bee)
01-03-03 21:34
No 395205
User Picture       Novel deoxygenation

Chem. Ber. p 1586 (1976)

Reduction of benzylic alcohols to hydrocarbons using PPh₃/I₂.

Captain_Mission
(Stranger / Eraser)
01-03-03 23:19
No 395219
      Referenced in the orgsyn article

This contains a preparation of acetonedicarboxylic acid from citric acid using concentrated instead of fuming H2SO4.

Ber. 17, 2543 (1884).

SpicyBrown
(Hive Bee)
01-04-03 02:20
No 395241
User Picture       Chem. Ber. p 1586 (1976)

Reduction of benzylic alcohols to hydrocarbons using PPh3/I2.

Ooooo, that sounds interesting. May be able to find this ref next week if nobody else comes up w/it in the meantime.

-SpicyBrown

Rhodium
(Chief Bee)
01-07-03 16:16
No 396152
User Picture       Synthesis of LSD

The Synthesis of ¹⁴C-diethylamine and lysergic acid diethylamide
Journal of Labelled Compounds and Radiopharmaceuticals 10:(2), 207 (1974)

Chimimanie
(Newbee)
01-13-03 16:49
No 397795
User Picture       synthesis of Ar-S-R from Ar-Br w/ Cu2+

Chalcogenolate ions and their derivatives. XVII. 2,3,8,9-tetraalkoxydibenzo[c,g]-1,2,5,6-tetrathiocin.    Woelki, Norbert; Klar, Guenter.   Inst. Anorg. Angew. Chem., Univ. Hamburg, Hamburg, Fed. Rep. Ger. Phosphorus and Sulfur and the Related Elements (1988), 36(3-4), 261-5. CODEN: PREEDF ISSN: 0308-664X. Journal written in German. CAN 110:57639 AN 1989:57639 CAPLUS

aromatic bromide ===BuSH, CuO, DMF==> corresponding butanethiol

Chimimanie
(Newbee)
01-16-03 23:12
No 398849
User Picture       other road to phenethylamine

From substituted benzaldehyde to the aldehyde one carbon further and to the bromide with Ph3P-CH2-OMe and then HClO4 for the aldehyde one carbon further and then NaBH4 then PPh3 and Br2 if you want the benzene ethyl bromide counterpart. May be interesting if you have access to PPh3

Org prep proced int 23(4), 419-24; 1991

Chimimanie
(Newbee)
01-21-03 14:26
No 400181
User Picture       synthesis of Ar-S-R from Ar-Br w/ Cu2+

New synthetic method for 2,5-dimethoxybenzaldehyde.
Chen, Zhi-tao; Xiang, Jian-nan; Li, Zhi-liang. College of Chemistry and Chemical Engineering, Chongqing University, Chungking, Peop. Rep. China.
Chongqing Daxue Xuebao, Ziran Kexueban (2002), 25(2), 109-111.
CODEN: CDXZF2 ISSN: 1000-582X. Journal written in Chinese. CAN 138:73048 AN 2002:335010 CAPLUS

Abstract

Reimer-Tiemann reaction and a methoxylation through di-Me sulfate are employed for the prepn. of 2,5-dimethoxybenzaldehyde from p-methoxyphenol in this paper. Comparing different phase transfer catalysts, it can be demonstrated that the PEG-10000 is the most favorable catalyst used in Reimer-Tiemann reaction. The yield and quality are improved through the methoxylation of 2-hydroxy-5-methoxy-benzaldehyde in a buffer soln. The diverse factors influencing the yield are examd. Some explanations are given from theor. viewpoint. The proper exptl. conditions are found and the overall yield reached 68%.

Rhodium
(Chief Bee)
01-22-03 17:08
No 400457
User Picture       NaBH4/I2

Sodium borohydride-iodine, an efficient reagent for reductive amination of aromatic aldehydes
Indian Journal of Chemistry Sect. B, 41(9), 1970-1971 (2002)

hermanroempp
(Hive Bee)
01-30-03 16:58
No 402681
      Reductive amination of ketones using Raney-Ni

Am. Soc. 70, 2811 (1948)

Title: n.a
Author: L. Haskelberg

Abstract: Reductive amination of various ketones in 17% ammoniacal ethanol with hydrogen in presence of Raney-Ni at atmospheric pressure and at room temperature. Я-phenylisopropylamine (aka amphetamine) is gotten in 85% yield from phenylacetone.

Quidquid agis, prudenter agas et respice finem!

Rhodium
(Chief Bee)
02-01-03 02:37
No 403150
User Picture       Protect the Pyrroles! Donate to Greenpeace!

Org Prep Proced Int 17(6), 391 (1985)
Protection of Indole in the 2-position with sodium bisulfite, hopefully making it possible to perform a one-pot Eschweiler-Clarke methylation (formic acid/formaldehyde) of tryptamine to DMT.

Rhodium
(Chief Bee)
02-18-03 23:35
No 409563
User Picture       Safrole derivatives

Isosafrole glycol preparation
Gazz.Chim.Ital. 36 I, 273 (1906)

Acid hydrolysis of isosafrole glycol leading to a mixture of MDP2P and MDP3P
Gazz. Chim. Ital. 42 I, 36 (1912)
Gazz. Chim. Ital. 36 I, 296 (1906)

Safrole epoxide + HBr -> Safrole bromohydrin
J Chem Res Miniprint 4, 1142-1165 (1982)

java
(Hive Bee)
02-22-03 18:27
No 410806
      Alcohol>>>methyl amine in one lab step

A one step process that works from alcohols to halides, to azides to methyl amine.....in one laboratory step.

Kosiara, A. Journal of Chemical Research Synopses, 1989, 296

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
02-24-03 05:24
No 411348
User Picture       Meth

Synth.Commun. 17; 6; 1987; 669-676.
Pd/C reduction of ephedrine to Meth

Rhodium
(Chief Bee)
02-24-03 05:27
No 411352
      Retrieved

Pharmacist's Article: 2,3-Dihydrobenzofuran Analogues of Hallucinogenic Phenethylamines (https://www.rhodium.ws/pdf/23-dihydrobenzofuran.pdf)

pHarmacist
(Hive Addict)
02-25-03 23:18
No 411616
User Picture       b-Asarone

Isolation of beta-asarone, an antibacterial and anthelmintic compound, from Acorus calamus in South Africa
South African Journal of Botany 68, 31-35 (2002)
LJ McGaw, AK Jäger and J van Staden

The aromatic rhizomes of Acorus calamus L. are used extensively in traditional medicine worldwide. They reportedly relieve stomach cramps, dysentery and asthma, and are used as anthelmintics, insecticides, tonics and stimulants. Alcoholic rhizome extracts of A. calamus growing in KwaZulu-Natal, South Africa, were previously found to have anthelmintic and antibacterial activity. Using bioassay-guided fractionation, the phenylpropanoid b-asarone was isolated from the rhizome. This compound was shown to possess anthelmintic and antibacterial activity. It has previously been isolated from A. calamus, and a related species, A. gramineus. Different varieties of A. calamus exhibit different levels of b-asarone, with the diploid variety containing none of the compound. Mammalian toxicity and carcinogenicity of asarones has been demonstrated by other researchers, supporting the discouragement of the medicinal use of Acorus calamus by traditional healers in South Africa.

Edit: Ref corrected and abstract retrieved by Java /Rhodium

Accept No Imitations, There Can Only Bee One; www.the-hive.ws

Rhodium
(Chief Bee)
02-28-03 00:48
No 412412
User Picture       4-bromo-2,5-dimethoxy-stuff

Fluorescent properties of DOB
Experientia; 27, 62 (1971)

4-bromo-2,5-dimethoxybenzaldehyde
J.Org.Chem.USSR (Engl.Transl.); 8; 1972; 339,340; Zh.Org.Khim.; 8; 1972; 340.

4-bromo-2,5-dimethoxy-benzaldehyde oxime
Synth. Commun. 28(24), 4629-4638 (1998)

Shulgin: 4-bromo-2,5-dimethoxy-beta-nitrostyrene
J.Pharm.Pharmacol. 37, 575-577 (1985)

Organikum
(Hive Addict)
02-28-03 20:50
No 412614
User Picture       L-PAC Biochemische Zeitschrift

The two basic articles on L-PAC:

Author: Neubert
- Biochemische Zeitschrift 115, 1921 S.282ff
and
- Biochemische Zeitschrift 128, 1922 S.610ff

thanks
ORG

ChemisTris
(Hive Bee)
03-02-03 01:37
No 412912
User Picture       Grignard and dimethoxybenzenes - Chimimanie

Chimimanie, Australian Journal of Chemistry (2000), 53(4), 245-256 has been scaned...
http://www.crosswinds.net/~blibrary/chemistry/index.html

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

Chimimanie
(Hive Bee)
03-02-03 11:28
No 413029
User Picture       Cool

Thank you ChemisTris smile , nice little article on LSD too cool .

The aust j chem article has got a preparation of bromo-dimethoxybenzene with KBr H2O2 but the 2,5dmb and phenylacetone are secondary product frown

ChemisTris
(Hive Bee)
03-07-03 07:27
No 414508
User Picture       alpha-asarone

New synthetic route for the preparation of potentially hypocholesterolemic analogs of alpha-asarone.
Determination of E/Z isomer content in natural and synthetic mixtures of alpha-asarone and its analogs.
Munoz, Heber; Diaz, Francisco; Sanchez, Adrian; Barajas, Marcelino; Labarrios, Fernando; Tamariz, Joaquin.
Acta Mexicana de Ciencia y Tecnologia (1993), 11(41), 51-62. (Spanish)

Abstract

A new and improved synthesis of potentially hypocholesterolemic (E)-2,4,5-R(MeO)2C6H2CH:CHMe [I, R = NO2, NH2] from eugenol is described. This pathway also allows the prepn. of the 2-propenyl analogs. Moreover, 5,6-dimethoxy-2-methylindole was also prepd. efficiently by this method. b-Asarone and (Z)-I [R = NO2] were also prepd. and the isomer ratios in natural and synthetic samples of a-asarone and I [R = NO2] detd. by GC/MS.

Further Information found by Java:

[Database Query form]
http://www.zblmath.fiz-karlsruhe.de/MATH/home

Acta Mexicana de Ciencia y Tecnologia. Nueva Epoca. Difusion Cientifica y Tecnologica del Instituto Politecnico Nacional, Zacatenco. (Formerly: Acta Mexicana de Ciencia y Tecnologia).

Abbreviation: Acta Mex. Cienc. Tecnol. Nueva Epoca ISSN: 0567-7785, Type: Journal, TIB: ZN 4235, GOE: ZA 31570

Library Reference:
TIB - Technische UniversitŠtsbibliothek Hannover
CWI - Centrum voor Wiskunde en Informatica, Amsterdam
GOE - Staats und UniversitŠtsbibliothek Goettingen
......this should get you one step closer, however I will keep looking.....java

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

Chimimanie
(Hive Bee)
03-07-03 19:08
No 414642
User Picture       2,5 dimethoxy-1-something useful

New synthetic method for 2,5-dimethoxybenzaldehyde.
Chen, Zhi-tao; Xiang, Jian-nan; Li, Zhi-liang. College of Chemistry and Chemical Engineering, Chongqing University, Chungking, Peop. Rep. China.
Chongqing Daxue Xuebao, Ziran Kexueban (2002), 25(2), 109-111.
CODEN: CDXZF2 ISSN: 1000-582X. Journal written in Chinese. CAN 138:73048 AN 2002:335010 CAPLUS

Abstract

Reimer-Tiemann reaction and a methoxylation through di-Me sulfate are employed for the prepn. of 2,5-dimethoxybenzaldehyde from p-methoxyphenol in this paper. Comparing different phase transfer catalysts, it can be demonstrated that the PEG-10000 is the most favorable catalyst used in Reimer-Tiemann reaction. The yield and quality are improved through the methoxylation of 2-hydroxy-5-methoxy-benzaldehyde in a buffer soln. The diverse factors influencing the yield are examd. Some explanations are given from theor. viewpoint. The proper exptl. conditions are found and the overall yield reached 68%.

An easy and fast method for oxidative deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers, and ethylene acetals with KMnO4 supported on alumina under solvent-free conditions.
Hajipour, A. R.; Mallakpour, S. E.; Baltork, I. M.; Backnezhad, H. Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Esfahan, Iran.
Synthetic Communications (2002), 32(5), 771-779.
CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 137:109096 AN 2002:226459 CAPLUS

Abstract

A manipulatively simple and rapid method for oxidn. deprotection of trimethylsilyl ethers, tetrahydropyranyl ethers and deprotection of ethylene acetals to afford carbonyl compds. under solvent-free conditions in the presence or absence of alumina with K permanganate.

Synthesis of alliodorin dimethyl ether.
Vig, O. P.; Sharma, S. D.; Verma, N. K.; Handa, V. K. Dep. Chem., Panjab Univ., Chandigarh, India.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1977), 15B(11), 988-90.
CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 88:191082 AN 1978:191082 CAPLUS

Abstract

Alliodorin di-Me ether (I) was prepd. in 10 steps from 2,5-(MeO)2C6H3COMe via Willgerodt reaction, redn., oxidn., Grignard reaction, Claisen rearrangement, Wittig reaction, etc.
Preparation of 2,5 dimethoxy phenylacetic acid, 2,5 dimethoxy phenylacetaldehyde and 2,5 dimethoxy phenyl ethanol.

Rhodium
(Chief Bee)
03-16-03 18:14
No 417622
User Picture       Synlett

Java: I posted the first one recently in Post 416740 (Rhodium: "Novel amino acid decarboxylation via the nitrile", Tryptamine Chemistry) and I have now uploaded the second to https://www.rhodium.ws/pdf/redamin.pd-hcook.pdf

You can get all Synthesis and Synlett articles for free by registering for a free trial with a fake name and fake email at Thieme's website: Post 363228 (Rhodium: "Free Online Chemistry & Medicinal Journals", Novel Discourse) When the free trial is over after 30-60 days, you just register a new fake name.

PolytheneSam
(Master Searcher)
03-16-03 20:39
No 417680
User Picture       Indian Patent 128,129 is now at ...

Indian Patent 128,129 is now at http://briefcase.yahoo.com/beefiles2001

http://www.geocities.com/dritte123/PSPF.html
The hardest thing to explain is the obvious

java
(Hive Bee)
03-17-03 01:46
No 417809
      Indian Patent is a ghost file........

patents
Êthis is what appears where the file shoudl be,
All Folders К|ÊFile FoldersÊ> patents
К
This folder is currently empty. ..................maybe try again....java

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

PolytheneSam
(Master Searcher)
03-17-03 01:56
No 417814
User Picture       Post 417799

Post 417799 (PolytheneSam: "Go to http://briefcase.yahoo.com log in as...", The Couch)

http://www.geocities.com/dritte123/PSPF.html
The hardest thing to explain is the obvious

Mountain_Girl
(Hive Bee)
03-17-03 11:15
No 418023
      Isolation of beta-asarone from Acorus Calamus...

Rhodium,

I have sent you (your ziplip address) a scanned copy of the following paper which Pharmacist referenced:
[obtained simply by asking over the internet]

Isolation of beta-asarone, an antibacterial and anthelmintic compound, from Acorus calamus in South Africa
South African Journal of Botany 68, 31-35 (2002)
LJ McGaw, AK Jäger and J van Staden

Edit by Rhodium: The file has been uploaded to https://www.rhodium.ws/pdf/asarone.southafrica.pdf

Mountain Boy

PolytheneSam
(Master Searcher)
03-20-03 01:40
No 419223
User Picture       The following is now at ...

The following is now at http://briefcase.yahoo.com/beefiles2001 in DejaVu format.

Synthesis of alliodorin dimethyl ether.
Vig, O. P.; Sharma, S. D.; Verma, N. K.; Handa, V. K. Dep. Chem., Panjab Univ., Chandigarh, India.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1977), 15B(11),
988-90.
CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 88:191082 AN 1978:191082
CAPLUS

Abstract

Alliodorin di-Me ether (I) was prepd. in 10 steps from 2,5-(MeO)2C6H3COMe via Willgerodt reaction, redn., oxidn., Grignard reaction, Claisen rearrangement, Wittig reaction, etc.
Preparation of 2,5 dimethoxy phenylacetic acid, 2,5 dimethoxy phenylacetaldehyde and 2,5 dimethoxy phenyl ethanol.

**********************************

Note on page 989 under Experimental Procedure

2,5-Dimethoxyacetophenone (II) -- It was prepared from dimethoxybenzene and acetyl chloride in the presence of anhyd. aluminium chloride according to the procedure described in literature⁵

Reference 5 is Ber. (1905), 789

Could you use chloroacetone in place of acetyl chloride to get 2,5-DimethoxyP2P? There seems to be a contradiction here
Post 346121 (Vibrating_Lights: "AlCl3 and Md compounds", Chemistry Discourse)

See also
Post 255616 (PolytheneSam: "Re: Substituted P2P's: Would this work?", Novel Discourse)
Post 255661 (PolytheneSam: "Re: Substituted P2P's: Would this work?", Novel Discourse)

The Indian journal does not go up to the year 2002 at the library where I found it.

http://www.geocities.com/dritte123/PSPF.html
The hardest thing to explain is the obvious

Mountain_Girl
(Hive Bee)
03-20-03 09:46
No 419376
      Can't find paper

The following is now at http://briefcase.yahoo.com/beefiles2001 in DejaVu format

Can't seem to find it - am I an idiot or is it just not there ?

Mountain Boy

PolytheneSam
(Master Searcher)
03-20-03 11:10
No 419395
User Picture       Its there now.

Its there now.

http://www.geocities.com/dritte123/PSPF.html
The hardest thing to explain is the obvious

Vitus_Verdegast
(Hive Bee)
03-27-03 16:56
No 421744
      Knoevenagel

Solvent-free Microwave Knoevenagel condensation catalyzed by NaCl or NH₄OAc-AcOH
Indian Journal of Chemistry, 2000, 39(6)
15 examples: 93-99% yield Using NaCl instead of NH₄OAc-AcOH: 15 examples, 90-98% yield

CoCl₂-Zn-DMF-H₂O : An efficient system for the reduction of aldehydes to alcohols.
Baruah, R.N.
Indian J. Chem., Sect B 33, 2, 182-83 (1994)

http://www.metafilter.com/comments.mefi/21638

Rhodium
(Chief Bee)
04-01-03 12:48
No 423002
User Picture       More interesting references

Synthesis of DOB by Bromination of 2,5-DMA with Elemental Bromine
Zh. Org. Chim. 8, 1330 (1972)

Synthesis of DOI from 2,5-DMA Using ICl
Journal of Labelled Compounds and Radiopharmaceuticals 14, 767 (1978)

Synthesis of DOI from DO-NH₂ Using NaNO₂, Piperidine & NaI
Journal of Labelled Compounds and Radiopharmaceuticals 23, 383 (1986)

Synthesis of 5-MeO-DMT
Journal of Labelled Compounds and Radiopharmaceuticals 33, 455 (1993)

Reduction of nitriles to amines using Cu²⁺/Al
Journal of Labelled Compounds and Radiopharmaceuticals 38, 385 (1996)

Synthesis of DMT
Journal of Labelled Compounds and Radiopharmaceuticals 38, 1021 (1996)

Comparative Review of Tropinone Reduction Methods
Tetrahedron 6, 319 (1959)

Synthesis of Psilocin
Heterocycles 47, 509 (1998)
Heterocycles 49, 451 (1998)
Heterocycles 51, 1131 (1999)

MDP2P from Safrole
Journal of the Indian Chemical Society 77, 453 (2000)

Synthesis of MDP2P
Synthetic Communications 24(2), 145 (1994)

Reduction of Oximes to Amines using NaBH₄/I₂/Ac₂O
Synthetic Communications 25, 3503 (1995)

One-Pot Synthesis of boc-Protected amines from Azides
Synthetic Communications 28(2), 261 (1998)

Identification and Quantitation of Gamma-Hydroxybutyrate (NaGHB) by Nuclear Magnetic Resonance Spectroscopy
Journal of Forensic Sciences 48(2), 292-298 (2003)

foxy2
(Distinctive Doe)
04-02-03 06:53
No 423262
User Picture       Rhodium

I have this and I'll try to scan it soon.

Microwave assisted Knoevenagel condensation using NaCl and
NH4OAc-AcOH system as catalysts under solvent-free conditions
Indian Journal of Chemistry, 2000, 39(6)

GC_MS
(Hive Addict)
04-02-03 17:16
No 423348
User Picture       wanted

D Trachsel. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationship. Part 1. Mescalin derivatives. Helv Chim Acta 85(9) (2002) 3019-?

The faster you run, the quicker you die.

Lego
(Stranger)
04-02-03 19:11
No 423371
      Helv. Chim. Acta. 2002, 85(9), 3019-3026

D Trachsel. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationship. Part 1. Mescalin derivatives. Helv Chim Acta 85(9) (2002) 3019-?

The article will be translated and posted soon. Be patient......

The candle that burns twice as bright burns half as long

Rhodium
(Chief Bee)
04-02-03 23:02
No 423428
User Picture       Synthesis of Novel Mescaline Derivatives

It has been on my site for a while, but it seems like I never came around to post a link to it... It is really great and describes the synthesis of a whole lot of novel mescaline derivatives - I have now posted it in Post 423427 (Rhodium: "Synthesis of Novel Mescaline Derivatives (German)", Novel Discourse).

Rhodium
(Chief Bee)
04-03-03 00:51
No 423453
User Picture       Indian Journal of Chemistry - Complete Ref

foxy2: Here is the exact reference for the article you didn't manage to find:

A facile oxidation of 1-naphthols to 1,4-naphthoquinones using active manganese dioxide.
Kumari, L. Krishna; Pardhasaradhi, M. Reg. Res. Lab., Hyderabad, India.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1982), 21B(12), 1067-70.
CODEN: IJSBDB ISSN: 0376-4699. CAN 99:53304 AN 1983:453304

Abstract

Selective oxidn. of 3,5-disubstituted 1-naphthols to the corresponding p-quinones is achieved using active MnO2. A facile synthesis of juglone by the oxidn. of 1,5-dihydroxynaphthalene by active MnO2 is also reported. Very good yields of 1,4-quinones are obtained when the starting phenols are 3,5-disubstituted.

Vitus_Verdegast
(Hive Bee)
04-09-03 01:34
No 424932
User Picture       new method for synthesis of heliotropin

High Selectivity in the Oxidation of Mandelic Acid Derivatives and in O-Methylation of Protocatechualdehyde: New Processes for Synthesis of Vanillin, iso-Vanillin, and Heliotropin
Hans-René Bjrsvik, Lucia Liguori, and Francesco Minisci
Org. Process Res. Dev.; 2000; 4(6) pp 534 - 543

http://www.geocities.com/Hollywood/Set/6240/belakrlf.jpg

java
(Hive Bee)
04-09-03 17:15
No 425135
      КК Reduction of Mesylate and NOT carbamate

The protection of the primary or secondary amine with a BOC group with subsequent Mesylation of the hydroxy group.

PNAS, Vol 69, pp. 730-732 (Proceedings from the National academy of Science)
ISSN: 00278424
OCLC: 43473694
LCCN: 00-227001

Synthesis and physical studies of azamitosene and iminoazamitosene reductive alkylating agents. Iminoquinone hydrolytic stability, syn/anti isomerization, and electrochemistry
Imadul Islam and Edward B. Skibo
pp 3195 - 3205

JOC, Vol 55, issue 10,pp. 3195-6
Editor: C. Dale Poulter, University of Utah
Email: joc@chem.utah.edu
Print Edition ISSN: 0022-3263
Web Edition ISSN: 1520-6904

Note: for bee's information

Digital Object Identifier

The Digital Object Identifier (DOI) system for digital media has been designed to provide persistent and reliable identification of digital objects. Information on the DOI and its governing body, the International DOI Foundation, can be found at http://www.doi.org. In the Web editions of ACS journals, the DOI appears at the top of the HTML version of an article and at the bottom of the first page in its PDF version; in the print editions, the DOI appears in the same location as in the PDF version.

Through use of the DOI, a publisher makes a commitment to maintain valid URLs pointing to their own digital content in a central directory maintained by the International DOI Foundation. Further information on the DOI can be obtained at http://dx.doi.org/10.1000/7. This link, which makes use of the DOI, provides access to a document which describes the DOI.

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Chimimanie
(Hive Bee)
04-09-03 17:48
No 425146
User Picture       J med Chem

Synthesis, Receptor Potency, and Selectivity of Halogenated Diphenylpiperidines as Serotonin 5-HT2A Ligands for PET or SPECT Brain Imaging.    Fu, Xing; Tan, Ping-Zhong; Kula, Nora S.; Baldessarini, Ross; Tamagnan, Gilles; Innis, Robert B.; Baldwin, Ronald M. Department of Psychiatry, Yale University School of Medicine and VA Connecticut Health Care Service, West Haven, CT, USA. Journal of Medicinal Chemistry (2002), 45(11), 2319-2324. CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 137:75305 AN 2002:319378 CAPLUS

Abstract

A series of 4'-substituted phenyl-4-piperidinylmethanol and benzoyl-4-piperidine derivs. was synthesized as potential novel serotonin 5-HT2A receptor ligands that can be radiolabeled for in vivo brain imaging. Compds. were prepd. by alkylation of 4-substituted benzoyl-4-piperidine with an iodo- or fluoro-substituted phenylalkyl halide followed by redn. with sodium borohydride. Potency of novel compds. was detd. by in vitro radioreceptor affinity assays selective for serotonin 5-HT2A receptors. Potent compds. were further evaluated for selectivity at serotonin-2A vs. 2C, 6, and 7, as well as dopamine D2 and adrenergic a1 and a2 receptors. The novel compd. (4-fluorophenyl)-(1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl)methanol (I) was particularly promising with high 5-HT2A potency (Ki = 1.63 nM) and >300-fold selectivity over other 5-HT receptor types.

Just to know wink

Lilienthal
(Moderator)
04-09-03 19:06
No 425163
User Picture       The DOI of the previous article is ...

The DOI of the previous article is DOI:10.1021/jm0200411. Please always give the DOI number (inside the new DOI: markup tag. Everybody with the right permission can then read (or download smile ) the pdf with one click!

The compounds from the previous article are not very interesting in our context - they are antagonists There are billions of articles about 5-HT2A antagonists...

Lego
(Stranger)
04-16-03 16:20
No 427296
      Comptes Rendus, 1969, 269(1), 51-3

Synthesis of psilocine from N, N-dimethyltryptamine

Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques (1969), 269(1), 51-3

CAN 71:70779 AN 1969:470779

Abstract: N,N-Dimethyltryptamine was oxidized by the Fenton-Cier reagent (A. Cier and C. Nofre, 1959) into psilocine.

Can anybee copy this article and perhaps there is a kind french-speaking bee who can translate it

Edit: Ref posted in Post 432605 (Chimimanie: "Wanted Mescaline synths", Novel Discourse) /Rhodium

The candle that burns twice as bright burns half as long

Rhodium
(Chief Bee)
04-16-03 23:12
No 427411
User Picture       Retrieved refs

twodogs:

J. Chem. Educ. 76, 1717 (1999) (https://www.rhodium.ws/pdf/hofmann-bleach.pdf)

Vitus_Verdegast:

Org. Proc. Res. Dev. 4, 534-543 (2000) (https://www.rhodium.ws/pdf/md-mandelic2piperonal.pdf)
(And if you look around you will find sections of this already posted here)

Antoncho:

Haworth and Lapworth, J. Chem. Soc., 121, 76 (1922) (https://www.rhodium.ws/djvu/acetalization.aldehydes.djvu)

Captain_Mission:

Direct conversion of Bromohydrins to ketones by a free radical elimination of HBr
J. Org. Chem. Vol. 67(1), 312-313(2002) (https://www.rhodium.ws/pdf/bromohydrin2ketone.pdf)

Simple, inexpensive procedure for the large-scale production of alkyl quinones
J. Org. Chem.; 1983; 48(17); 2932-2933. (https://www.rhodium.ws/pdf/large-scale.alkyl-quinones.pdf)

Antoncho
(Official Hive Translator)
04-19-03 04:16
No 427975
      Could someone please look this up?

Haworth and Lapworth, J. Chem. Soc., 121, 76 (1922).

Reduction of m-nitro-benzaldehyde to aminoBA with Na2S.

Noelting, Ann. chim., (8) 19, 541 (1910).

Reaction of diazotized m-amino-BA with MeOH to yield m-MeO-BA

To complete the picture, here are the remaining pieces:

Nitration of benzaldehyde: Patent US1509412

Diazotization of m-amino-BA: http://orgsyn.org/orgsyn/prep.asp?prep=cv3p0564

Antoncho

Rhodium
(Chief Bee)
04-25-03 00:39
No 429225
User Picture       Desirable Articles

Behavioral properties of psychoactive phenylisopropylamines in rats
Richard A. Glennon, John A. Rosecrans and Richard Young
European Journal of Pharmacology, Volume 76, Issue 4, 17 December 1981, Pages 353-360.
DOI:10.1016/0014-2999(81)90106-0

Abstract:

Rats were trained to discriminate injections of 5-methoxy.N,N-dimethyltryptamine (5-OMe DMT. 3.0 mg/kg), a hallucinogenic agent for which a serotonergic mechanism has been implicated. from sahine in a two-lever drug discrimination task. After reliable levels of accuracy (>85%) were attained, the ability of the 5-OMe DMT cue to generalize to 36 substituted phenylisopropylamines (or their optical isomers) was assessed. The results reveal that. in general, the challenge compounds could be differentiated into three broad categories: Those that produced 5-OMe DMT-appropriate responding (generalization), those that produced partial 5-OMe DMT.appropriate responding (partial generalization) and those that produced negligible 5-OMe DMT-appropriate responding. It is concluded that certain of the substituted phenylisopropylamines. unlike amphetamine itself, can produce effects in rats similar to those produced by the training dose of 5-OMe DMT. and that a serotonergic mechanism might be involved.

Discriminative stimulus properties of DOM and several molecular modifications
Richard A. Glennon, Richard Young and John A. Rosecrans
Pharmacology Biochemistry and Behavior Volume 16, Issue 4 , April 1982, Pages 553-556
DOI:10.1016/0091-3057(82)90413-0

Abstract:

Rats trained to discriminate racemic 2,5-dimethoxy-4-methylphenylisopropylamine, (±)-DOM (1.0 mg/kg), from saline in a two-lever drug discrimination task were challenged with the optical isomers of DOM as well as with several related agents which represent minor molecular modifications of the DOM structure. Generalization of the (±)-DOM stimulus was found to occur to R(-)-DOM, S(+)-DOM, (±)-2,5-dimethoxyphenylisopropylamine (2,5-DMA), R(-)-2,-5-DMA, and the 2-demethyl derivative of (±)-DOM. The 3-methyl positional isomer of (±)-DOM was found to produce only 34% DOM-appropriate responding at the highest dose tested while administration of S(+)-2,5-DMA and the 5-demethyl derivative of (±)-DOM resulted in disruption of behavior.

Vitus_Verdegast
(Hive Bee)
04-27-03 21:17
No 429814
User Picture       refs that could be interesting

CoCl₂-Zn-DMF-H₂O : An efficient system for the reduction of aldehydes to alcohols. Baruah, R.N. : Indian J. Chem., Sect B 33, 2, 182-83 (1994)

http://www.ealasaid.com/fan/lorrelibrary/b-wing/bc/intro.wav

ChemisTris
(Hive Bee)
04-29-03 14:30
No 430194
User Picture       Retrieved refs.

Rhodium:
Behavioral properties of psychoactive phenylisopropylamines in rats
Richard A. Glennon, John A. Rosecrans and Richard Young
European Journal of Pharmacology, Volume 76, Issue 4, 17 December 1981, Pages 353-360.
http://mishmashblue.tripod.com/euro.pdf

Did foxy2 scan Synthesis of MDP2P Synthetic Communications 24(2), 145 (1994) yet?
if not it's here:
http://mishmashblue.tripod.com/syncom.pdf

Vitus_Verdegast:
Heterocycles 46, 91-94 (1997)
http://mishmashblue.tripod.com/heterocycles.djvu

J. Nat. Prod. 60(11), 1196-98 (1997)
http://mishmashblue.tripod.com/np60.pdf

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

Rhodium
(Chief Bee)
05-02-03 19:43
No 430916
User Picture       Methadone

PTC alkylation of Ph₂CHCN in the synthesis of Methadone
J. Chem. Res. Miniprint (7) 2484-2492 (1981)

Phenyl-substituted normethadones: synthesis and pharmacology
J Pharm Pharmacol 1995 Mar;47(3):237-42
Medline (PMID=7602488)

Methadone NMR Analysis
Sci. Pharm. 68(3), 229-234 (2000)

A Novel Approach to Isomeric Part (+/-)-Methadone
Sci. Pharm. 64(3/4), 271-278 (1996)
Bracher, Franz; Klein, Katrin; Litz, Thomas

Abstract
Alkylation of deprotonated diphenylacetonitrile (2) with an acetal of chloroacetone followed by acidic hydrolysis and reductive amination of the resulting ketonitrile 12 offered an easy access to the methadone precursor 3. By this pathway the formation of the undesired regioisomer 4 was avoided.

GC_MS
(Hive Addict)
05-02-03 20:10
No 430922
User Picture       Sci Pharm?

Sci Pharm = Sciences pharmacologiques, and is a French magazine?

EDIT: I can most probably get my hands on Sci Pharm and J Pharm Sci, but you must be patient till monday wink . J Pharm Sci for sure; Sci Pharm is in doubt.

The faster you run, the quicker you die.

Lego
(Stranger)
05-02-03 21:32
No 430940
User Picture       Sci. Pharm = Scientia Pharmaceutica

Sci. Pharm = Scientia Pharmaceutica (not a french journal, it is an austrian journal, with no online access frown )

The candle that burns twice as bright burns half as long

Lego
(Stranger)
05-02-03 22:03
No 430947
User Picture       Preparation of of indol-3-yl-thioacetamide

Preparation of of indol-3-yl-thioacetamide

Lego's voice: N,N-substituted indol-3-yl-thioacetamides could bee valuable precursors for N,N-substituted tryptamines as thioamides are easily reduced to the corresponding amines.

Piotrowska et al.; ROCHAC; Rocz.Chem.; 50; 1976; 603.

Edit: retrieved in Post 444356 (Rhodium: "References for Barium & Lego", Novel Discourse) /Rhodium

The candle that burns twice as bright burns half as long

Rhodium
(Chief Bee)
05-05-03 01:15
No 431408
User Picture       Refs for Captain_Mission

Refs for Captain_Mission:

Direct conversion of Bromohydrins to ketones by a free radical elimination of HBr
J. Org. Chem. Vol. 67(1), 312-313(2002) (https://www.rhodium.ws/pdf/bromohydrin2ketone.pdf)

Simple, inexpensive procedure for the large-scale production of alkyl quinones
J. Org. Chem.; 1983; 48(17); 2932-2933. (https://www.rhodium.ws/pdf/large-scale.alkyl-quinones.pdf)

Chimimanie
(Hive Bee)
05-11-03 09:45
No 432605
User Picture       Wanted Mescaline synths

Various Mescaline synthesis:

see post Post 432604 (Chimimanie: "Mescaline synthesis", Novel Discourse)

(a) L. Reti, in: R.H.F. Manske, H.L. Holmes (Eds.), The Alkaloids Tome III, 1953, p. 313.
(g) M.N.Aboul-Enein, A.I. Eid Acta Pharm. Suec 16 (1979) 267.

The reference (g) should bee the more interesting and is highly wanted

Rhodium
(Chief Bee)
05-11-03 17:57
No 432646
User Picture       Zinc/hydrazine for reduction of nitro compounds

Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds
Gowda, Shankare, Gowda, D Channe
Indian Journal Of Chemistry. Sect. B. 42(1), 180-183 (2003)

And while looking up the article above, please check whether the article below oxidizes the eugenol to something of interest:

Copper(II)--cyclodextrin aided oxidation of eugenol
Pattekhan, H H, Divakar, S
Indian Journal Of Chemistry. Sect. B. 42(2), 369-371 (2003)

Rhodium
(Chief Bee)
05-15-03 10:42
No 433308
User Picture       Journal of Organometallic Chemistry

Silane reductions in acidic media VIII. Boron trifluoride catalyzed organosilane reductions. selectivity and mechanism
Journal of Organometallic Chemistry Volume 117, Issue 2 , 7 September 1976, Pages 129-140
DOI:10.1016/S0022-328X(00)87264-2

Rhodium
(Chief Bee)
05-21-03 15:28
No 434562
User Picture       More Methadone & Other refs

Synthesis of Methadone Nitrile etc.
Journal of Labelled Compounds and Radiopharmaceuticals 22(1), 5-22 (1985)

Methadone Chemistry
J. Pharm. Sci. 66(11), 1579-82 (1977)

Analysis of Clandestinely Manufactured Methadone
Archiv für Kriminologie 159(5-6), 144-150 (1977)
Archiv für Kriminologie 164(3-4), 83-85 (1979)

PTC alkylation of Ph₂CHCN in the synthesis of Methadone
J. Chem. Res. Miniprint (7) 2484-2492 (1981)

Phenyl-substituted normethadones: synthesis and pharmacology
J Pharm Pharmacol 1995 Mar;47(3):237-42
Medline (PMID=7602488)

Methadone NMR Analysis
Sci. Pharm. 68(3), 229-234 (2000)

High-yielding Aromatic Iodination with I₂/HgO
Proceed. Royal. Acad. A413, 191 (1933)

Review of NaBH₃CN Reductive Amination
Org. Prep. Proced. Int. 11(5), 201 (1979)

Review of Acyloxyborohydride Reductions
Org. Prep. Proced. Int. 17(4-5), 317-384 (1985)

Demethylation of 1,3-MeO-benzenes (Good for Olivetol prep & Eugenol)
Org. Prep. Proced. Int. 28, 371 (1996)

Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds
Gowda, Shankare, Gowda, D Channe
Indian Journal Of Chemistry. Sect. B. 42(1), 180-183 (2003)

And while looking up the article above, please check whether the article below oxidizes the eugenol to something of interest:

Copper(II)--cyclodextrin aided oxidation of eugenol
Pattekhan, H H, Divakar, S
Indian Journal Of Chemistry. Sect. B. 42(2), 369-371 (2003)

algebra
(Stranger)
05-29-03 20:58
No 436410
      wanted refs.

This reference which discusses DXM would also be a very useful addition to the Levorphanol synth on Rhodium's by DopaMan, https://www.rhodium.ws/chemistry/levorphanol.html

The synth for this powerful opiate is very straightforward except for the difficulty in obtaining 2-(1,4-Cyclohexadienyl)ethylamine. This compound can be made from PEA (decarboxylate phenylalanine) with a controlled birch reduction of the ring, however the reference given here would seem to procede from cyclohexanone or cyclohexanol which would offer a far simpler route.

Preparation of useful intermediates of dextrorphan
Passarotti, C. M.; Valenti, M.; Grianti, M.
Boll.Chim.Farm. 1993, 132: 11 472-474

Abstract
Dextrorphan is the main metabolite of Dextromethorphan, a drug with high anti-tussive activity.In this preliminary work we report on the synthesis of two essential intermediates for its preparation: 2-(1-cyclohexenyl)ethyl amine and (R;S)-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline.

pHarmacist
(pHantasticant)
06-01-03 12:40
No 436968
User Picture       Isotryptamines:

Photochemical synthesis of 2-(2-aminoethyl)indole (isotryptamine) derivatives
Victor Snieckus and Kuldip S. Bhandari
Tetrahedron Letters Volume 10, Issue 39 , 1969, Pages 3375-3376

Accept No Imitations, There Can Only Bee One; www.the-hive.ws

Rhodium
(Chief Bee)
06-03-03 12:59
No 437522
User Picture       Mescaline Refs for Chimimanie

Chimimanie:

The Alkaloids, Vol III:
https://www.rhodium.ws/pdf/the.alkaloids.vol3.ch22.pea.pdf

Acta Pharm. Suecia 16, 267-270 (1979)
https://www.rhodium.ws/chemistry/mescaline.html (Under the heading "A Novel Route for the Synthesis of Mescaline")

Rhodium
(Chief Bee)
06-03-03 23:55
No 437667
User Picture       From safrole to anything?

Journal of Chemical Research (Miniprint), p 1142-1165 (1982)

The article describes all the procedures below, really interesting if you ask me. Don't bother to retrieve the "Synopsis" edition, as it contains nothing but these schematics, the procedures are only to be found in the "Miniprint" edition.

ChemisTris
(Hive Bee)
06-04-03 01:43
No 437677
User Picture       re: isotryptamines

pHarmacist, Tetrahedron Letters Volume 10, Issue 39 , 1969, Pages 3375-3376 is here:
http://mishmashblue.tripod.com/isotryptamine.pdf

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

Rhodium
(Chief Bee)
06-10-03 12:57
No 439047
User Picture       Arylation articles for java

Arylation of several carbanions by the SRN1 mechanism
Roberto A. Rossi, J. F. Bunnett;
J. Org. Chem.; 1973; 38(17); 3020-3025. (https://www.rhodium.ws/pdf/srn1.arylation-1.pdf)

SRN1 phenylation of nitrile carbanions and ensuing reactions. New route to alkylbenzenes
J. F. Bunnett, Bernhard F. Gloor;
J. Org. Chem.; 1973; 38(24); 4156-4163. (https://www.rhodium.ws/pdf/srn1.arylation-2.pdf)

Mesitylation and phenylation of picolyl anions by the SRN1 mechanism
J. F. Bunnett, Bernhard F. Gloor;
J. Org. Chem.; 1974; 39(3); 382-384. (https://www.rhodium.ws/pdf/srn1.arylation-3.pdf)

And if you are intrerested in the above, I suggest that you take a look at the articles below:

https://www.rhodium.ws/pdf/archive/alpha-arylation.html
https://www.rhodium.ws/pdf/archive/alpha-arylation.carbonyls-nitriles.html

Rhodium
(Chief Bee)
06-10-03 22:28
No 439170
User Picture       Berichte for Java

Chem. Ber. 89, 2641-2644 (1956) (https://www.rhodium.ws/pdf/archive/cumylhydroperoxide.pdf)

Vitus_Verdegast
(Hive Bee)
06-14-03 16:34
No 440003
      5-iodo-2-aminoindan

"5-iodo-2-aminoindan, a non-neurotoxic analogue of p-iodo-amphetamine" Nichols, D.E.; Johnson, M.P. and Oberlender, P.
Pharmacol. Biochem. Behav. 38, 1, p.135 (1991)

DOI:10.1016/0091-3057(91)90601-W

Could someone dig this one up? Thanks.

http://hes.iki.fi/video/LSD_Being_Tested_on_Brtish_Troops.mpg

java
(Hive Bee)
06-18-03 21:04
No 440876
      Addition of Halogen and an amino groupto alkenes,.

-C=C- + R2NCl.....>>>>>H2SO4, HOAc>>>- -C(Cl)-C(NR2)-

"The groups R2N and Cl can be added directly to alkenes, allenes, conjugated dienes and alkynes, by the treatment with dialkyl-N-chloroamines and acids. * These are free-radical additions with initial attack by the R2NH+ radical ion.** N-Halo amides (RCONHX) add RCONH and X to double bonds under the influence of UV light or chromous chloride.*** Amines add to allenes in the presence of a palladium catalyst**** "

Needed References;

Minesci, F.;Galli, R. ;Cecere, M. ;-Tetrahedral Lett. ,1966,3163

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
06-19-03 13:43
No 441011
User Picture       Radical References for Java

For Java:

Chemistry of nitrogen radicals. VI. The free-radical addition of dialkyl-N-chloramines to substituted olefins
J. Org. Chem.; 1967; 32(11); 3273-3284. (https://www.rhodium.ws/pdf/archive/vinylic.aminochlorination.pdf)

Nonaromatic aminium radicals
Chem. Rev.; 1978; 78(3); 243-274. (https://www.rhodium.ws/pdf/archive/nonaromatic.aminium.radicals.review.pdf)

Rhodium
(Chief Bee)
06-20-03 19:38
No 441371
User Picture       For Aurelius: BDO & THF -> GBL

As requested by Aurelius in Post 439780 (Aurelius: "Compilation on GHB/GBL", Methods Discourse)

Direct Conversions of Ethers to Esters by Trichloroisocyanuric Acid
Tet. Lett. 55, 5819-5820 (1968) (https://www.rhodium.ws/pdf/ethers2esters.trichloroisocyanuric.pdf)

The Oxidation of Alcohols and Ethers Using Calcium Hypochlorite [ Ca(OCl)₂ ]
Tet. Lett. 23(1), 35-38 (1982) (https://www.rhodium.ws/pdf/roh-ror2esters.pdf)

Oxidation Studies of Symmetrical and Unsymmetriclal Ethers - Comparison of Trichloroisocyanuric Acid and Hypochlorous Acid
Tetrahedron 27, 2671-2674 (1971) (https://www.rhodium.ws/pdf/)

Rhodium
(Chief Bee)
06-20-03 22:25
No 441401
User Picture       Wanted: 1,4-Butanediol to gamma-Butyrolactone

Production of -butyrolactone by liquid phase oxidation of 1,4-butanediol
Mukhopadhyay S., Chandalia S.B.,
Indian J. Chem. Technol., Vol. 6, No. 4, 237–239 (1999)

GC_MS
(Hive Addict)
06-26-03 08:08
No 442644
User Picture       wanted

RT Gilsdorf, FF Nord. Reverse addition of lithium aluminum hydride to nitroolefins. JACS 74 (1952) 1837-1843.

Should describe the reduction of nitroalkene to nitroalkane (via LAH), followed by conversion of the nitroalkane to propanone (first NaOH, followed by H2SO4). Mentioned in TFSE but not typed out.

The faster you run, the quicker you die.

Rhodium
(Chief Bee)
06-26-03 14:20
No 442685
User Picture       GC_MS: Reverse Addition of LAH to Nitroalkenes

Reverse Addition of Lithium Aluminum Hydride to Nitroolefins
R. T. Gilsdorf, F. F. Nord;
J. Am. Chem. Soc.; 1952; 74(7); 1837-1843. (https://www.rhodium.ws/pdf/lah-nitroalkenes.reverse-addition.pdf)

Mentioned in TFSE but not typed out.

It would be wonderful if the interesting parts were... But you probably need an OCR program - PM me if you want one.

java
(Hive Bee)
06-27-03 02:30
No 442788
      Reduction of Carboxylic Acid Imidazolides.......

Facile Reduction of Carboxylic Acid Imidazolides to Primary Alcohols in the Presence of Water

Synlett 1995; 839-840
DOI: 10.1055/s-1995-5096

Rajiv Sharma1, George H. Voynov, Timo V. Ovaska2, Victor E. Marquez

A convenient protocol for selective reduction of carboxylic acid imidazolides to primary alcohols, which tolerates bromo, nitro, cyano, ester and amide functional groups, is disclosed.

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
06-27-03 09:00
No 442856
User Picture       Synlett is available online

Java: You can fetch any Synlett or Synthesis article for free by signing up for Thieme's 30-day trial: Post 363228 (Rhodium: "Free Online Chemistry & Medicinal Journals", Novel Discourse)

Here is the last of your radical related articles though: Tet. Lett. 3163-3166 (1966) (https://www.rhodium.ws/pdf/archive/radical.n-chloroamine.addn.alkenes.pdf)

Barium
(Heavyweight Chempion(eer))
07-01-03 13:57
No 443784
      Wanted refs

Jonzyk; Kwast; Makosa, J.Chem. Soc., Chem. Commun. (1977), 902
Gladiali; Soccolini, Synth. Commun. (1982), 12, 355

Sipos; Schöbel; Balaspiri, J. Chem. Soc. C (1970), 1154
Sipos; Schöbel; Sirokman, J. Chem. Soc., Perkin Trans. 2 (1975), 805

Edit: all retrieved in Post 444356 (Rhodium: "References for Barium & Lego", Novel Discourse) /Rhodium

Close to fucking furious because of backstabbing assholes roaming free here

Kinetic
(Hive Bee)
07-04-03 01:00
No 444342
      That journal again...

Zinc chloride catalysed 2,2-dialkyl benzodioxole acylations with acetic anhydride, yields over 90%:

Indian J.Chem.Sect.B; 38; 2; 1999; 137 - 140.

I'd really appreciate it if someone could find this - the most important part is the workup/purification, but the whole article would be nice too. smile

Rhodium
(Chief Bee)
07-04-03 02:09
No 444356
User Picture       References for Barium & Lego

All References below fetched/scanned by lugh, I merely host them.

For Barium:

The Darzen Condensation, Part I
J. Chem. Soc. C (1970), 1154 (https://www.rhodium.ws/djvu/sipos1.djvu)

The Darzen Condensation, Part III
J. Chem. Soc., Perkin Trans. 2 (1975), 805 (https://www.rhodium.ws/djvu/sipos2.djvu)

Stereochemical Control of the Darzens Condensation
J.Chem. Soc., Chem. Commun. (1977), 902 (https://www.rhodium.ws/djvu/jonczyk.djvu)

Synthesis of Glycidic esters in a two-phase solid-liquid system
Synth. Commun. (1982), 12, 355 (https://www.rhodium.ws/djvu/gladiali.djvu)

For Lego:

New Sulfur Derivatives Of Indoles
Rocz. Chem.; 50; 1976; 603. (https://www.rhodium.ws/djvu/piotrowska.djvu)

Rhodium
(Chief Bee)
07-07-03 01:41
No 445047
User Picture       Wanted: NaBH4 Reductive Monomethylation

Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of -amino acids and -amino methyl esters
Can. J. Chem./Rev. Can. Chim. 80(7): 779-788 (2002)
DOI:10.1139/v02-083

Full abstract available in Post 445024 (Vitus_Verdegast: "Found this:", Tryptamine Chemistry)

java
(Hive Bee)
07-07-03 19:52
No 445298
      Preparation of Thionyl chloride

JSC Journal Society Chemistry
117, pg 1103, (1920)

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
07-08-03 00:45
No 445385
User Picture       P2P by Hydrolysis of PPA & Ephedrine alkaloids

Optically Active Phenylpropanolamine Derivatives: IX. Abnormal Hydramine Fission.
Takamatsu, H.
J. Pharm. Soc. Japan, Vol. 76, 1956, pp. 1219-1222.

jimwig
(Hive Bee)
07-08-03 22:44
No 445691
      Zh. Obsh. Khim./Yakugaku Zasshi @ GaTech

GaTech has volume 18 Zhurnal obshchei khimii.

Zhurnal obshchei khimii
t. 1- 1931- (Vol. 1- also called vol. 63- .)
Call Number: QD1 .R9

Note: Periodical volumes published through 1979 are in storage. For retrieval, ask at Circulation Desk, 1st Floor East.
Library has also English translation: Journal of general chemistry of the USSR.
Library has: v.9, 1939@v.16--v.50, 1946--1980@v.[51, pt.1]; Jan.-Mar. 1981@v.51, pt.2--v.51, pt.4; Apr.-Dec. 1981.

Contact them and request a photocopy of the article you wish. It will probably be in Russian. Hey no problem.

GaTech has volume 76 of J. Pharm. Soc:

Yakugaku zasshi (Journal of the Pharmaceutical Society of Japan)
Georgia Institute of Technology, Summary hold: Vol/No: 1-99 (1881-1979), Call No: RS1 .N56 A2X

jimwig
(Hive Bee)
07-08-03 23:19
No 445702
      GaTech has volume 76 of J. Pharm. Soc

Yakugaku zasshi.
Journal of the Pharmaceutical Society of Japan.
Nippon Yakugakkai.; Nihon Yakugakkai.

1881-
Japanese Serial Publication : Periodical : Monthly no. ill. 26 cm.
Tokyo, Pharmaceutical Society of Japan.

GEORGIA INST OF TECH (GAT)
Summary Hold: Format: Paper
Vol/No: 1-99 1881-1979
not currently received
Call No: RS1 .N56 A2X
Date of Info: 19910900
Location(s): GATT
Vol/No: 1-99 1881-1979
permanently retained; not currently received

GC_MS
(Hive Addict)
07-10-03 09:32
No 446126
User Picture       Sodium Percarbonate in Synth. Commun.

Sodium Percarbonate: A Mild Reagent for Conversion of Tosylhydrazones and Nitroalkanes to Carbonyl Compounds
C Narayana, NK Reddy. GW Kabalka
Synth. Commun. 22(17), 2587-2592 (1992)

Abstract

Sodium percarbonate has been found to be a good reagent for oxidative regeneration of carbonyl compounds from tosyl hydrazones and nitroalkanes.

Dirty old man

Rhodium
(Chief Bee)
07-12-03 00:16
No 446489
User Picture       2C-B article retrieved by Java

4-bromo-2,5-dimethoxyphenethylamine (2C-B): A review of the public domain literature.
Cole M.D,Lea C and Oxley N.
Science & Justice 42(4), 223-224 (2002) (https://www.rhodium.ws/pdf/2c-b.review.pdf)

jimwig
(Hive Bee)
07-12-03 15:37
No 446622
      is it rolling, Bob? Notice on the end of the...

is it rolling, Bob?

Notice on the end of the results list posted above that this is an INTERNATIONAL sourcing. That is the names listed in Great Britain and Europe can be accessed by bees other than those of us in the greatest country on the planet.

You guessed it - LIberia........

Rhodium
(Chief Bee)
07-15-03 14:48
No 447475
User Picture       Wanted: Synthesis of DMT

Trifluoroacetylation of Methylated-Derivatives of Tryptamine and Serotonine by Different Reagents: Synthesis, Spectroscopic Characterizations, and Separations by Capillary-Gas-Chromatography
Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas
Zeitschrift für Naturforschung B, Vol 54, No 3, 397-414 (1999)

Rhodium
(Chief Bee)
07-16-03 00:25
No 447617
User Picture       Friedel-Craft alkylation for Aurelius

Allylbenzenes by Friedel-Craft alkylation with Allyl Alcohol, catalyzed by K-10 Acidic Clay
J. Chem. Soc. Perkin Trans 1, 3519-3520 (1994) (https://www.rhodium.ws/pdf/fc-alkylation.k10-clay.pdf)

The article has earlier been discussed and partly typed up in Post 103617 (Scooby Doo: "Alkylation of 1,3benzodioxole with K10", Chemistry Discourse) and Post 108727 (dormouse: "Allylpyrocatechol question -bloodgod100", Novel Discourse).

Rhodium
(Chief Bee)
07-18-03 00:25
No 448135
User Picture       Nef rxn Reference for GC_MS + DMT synthesis

For GC_MS:

Sodium Percarbonate: A Mild Reagent for Conversion of Tosylhydrazones and Nitroalkanes to Carbonyl Compounds
C Narayana, NK Reddy. GW Kabalka
Synth. Commun. 22(17), 2587-2592 (1992) (https://www.rhodium.ws/djvu/nef.sodium.percarbonate.djvu)

The article below lacks page 414, but it will hopefully be corrected soon:

Trifluoroacetylation of Methylated-Derivatives of Tryptamine and Serotonine by Different Reagents: Synthesis, Spectroscopic Characterizations, and Separations by Capillary-Gas-Chromatography
Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas
Zeitschrift für Naturforschung B, Vol 54, No 3, 397-414 (1999) (https://www.rhodium.ws/djvu/dmt.nmt.trifluoroacetate.djvu)

Rhodium
(Chief Bee)
07-18-03 01:56
No 448153
User Picture       Articles Retrieved by lugh

Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of -amino acids and -amino methyl esters
Can. J. Chem./Rev. Can. Chim. 80(7): 779-788 (2002) (https://www.rhodium.ws/djvu/nabh4.n-monoalkylation.djvu)

Benzene Hydrocarbons with a Pseudo Allyl Side Chain: Methovinylbenzene and its Homologues. Study of Certain Molecular Migrations. Second Part. Study of Molecular Transpositions which Accompany the Transformation of -Glycols and their Derivatives into Aldehydes and Ketones.
Tiffeneau, M.
Ann. chim. phys., [8], Vol 10, pp 322-78 (1908) (https://www.rhodium.ws/djvu/tiffeneau.carbures-benzenique.djvu)
Abstract: Post 446645 (Rhodium: "Glycols, halohydrins & epoxides to P2P", Novel Discourse)

Preparation of Optically Active -aminopropiophenones by asymmetric transformation
H. Takamatsu
J. Pharm. Soc. Japan, Vol. 76, 1219-1222 (1956) (https://www.rhodium.ws/djvu/takamatsu.djvu)

Chimimanie
(Hive Bee)
07-24-03 02:53
No 449379
User Picture       2,5 dimethoxy phenethyl chloride

Synthesis and some properties of 1,2-dihydro-4,7-dihydroxycyclobuta{b}naphthalene-3,8-dione and 1,2,5,6-tetrahydro-4,7-dihydroxydicyclobuta{b,g}naphthalene-3,8-dione.
Watabe, Takashi; Oda, Masaji
Chemistry Letters (1984),   (10), 1791-4.

It render more OTC the 2CH synth, using mercury/ethene to the phenethylalcohol, then with this ref we got the chloride OTC, then azide swap/reduct or Kphtalimide in DMF reflux, followed by ethanolamine treatment (sadly the patent on that is in japanese frown )

Rhodium
(Chief Bee)
07-24-03 17:03
No 449557
User Picture       JOC for Chimimanie

The J Org Chem 49(9), 1603 (1984) article is now linked in the reference section of https://www.rhodium.ws/chemistry/p2p.manganese.html

Aurelius
(Active Asperger Archivist)
07-24-03 18:59
No 449586
      Rhodium

your link isn't working. we only get the <a href command

Act quickly or not at all.

Rhodium
(Chief Bee)
07-25-03 02:51
No 449668
User Picture       Berichte: 2,5-Dimethoxyphenyl-1-chloroethane

Chimimanie:

The use of nitrilium salts in the synthesis of heterocyclic compounds. I. Derivatives of 3,4-dihydroisoquinoline
Lora-Tamayo, Manuel; Madronero, Ramon; Munoz, Guillermo Garcia
Chem. Ber. 93, 289-297 (1960) (https://www.rhodium.ws/pdf/25-meo-phenethylchloride.pdf)

Tdurden969
(Hive Bee)
07-25-03 05:44
No 449704
      Sodium Tetrahydridoborate

E. Gyenge and C. Oloman, "Attempts at the Electrosynthesis of Borohydride". Journal of Applied Electrochemistry 28, 1147-1151, 1998

Couldn't find an abstract - might be interesting

Sonson
(West Coast Cowboy)
07-25-03 11:23
No 449753
      The stereoisomers of 4-metyhlaminorex. J.

The stereoisomers of 4-metyhlaminorex.
J. Forensic Sci. 34 (1989) 962-979.

Anyone?

Chimimanie
(Hive Bee)
07-25-03 13:52
No 449768
User Picture       On chlorination

Those two articles, referenced in the berichte one, please smile

J. F. NORRIS and H. B. TAYLOR J Am Chem Soc 46, 753 (1924)

That article describe the phenethyl alcohol to chloride swap. I wanna all the text if possible.

To see the usefulness of the method in a synthesis of DOI from the isopropanol.

This one too:

R. A. BARNES, J Am Chem Soc 75, 3004 (1953)

It describe the synthesis of the 2,5-dimethoxy ethanol. The experimental suffice wink .

Thanx cool

BTW, thank you Rhodium! wink

java
(Hive Bee)
07-26-03 22:20
No 450020
      Nitrosation of propiophenones

Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)
Michael P. Johnson, Stewart P. Frescas, Robert Oberlender, and David E. Nichols

J. Med. Chem. 1991, 34, 1662-1668

Edited: Thanks to Kinetic, he was able to find some of the article in an old post but not in its entirety...

Post 122807 (dormouse: "Benzofuran, indan and tetralin analogues of MDA. -Nemesis", Serious Chemistry)

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
07-27-03 22:27
No 450247
User Picture       I'd like...

Synthesis of 2-carbomethoxy-3-(fluorophenyl)tropane ([18F]CFT or [18F]WIN 35428)
Bergman J, Haaparanta M and Solin O
J. Label. Comp. Radiopharm. 1995; 37: 46-48.

Kinetic
(Hive Bee)
07-29-03 07:56
No 450519
      Retrieved

Kinetic has now managed to trawl up the JMC article in it's entirety for java, but has nowhere to host it.

Also retrieved are the following:

For Chimimanie tongue

Tetrahedron Letters, Volume 35, Issue 34, Pages 6207-6210

J Am Chem Soc 46, 753 (1924),

J Am Chem Soc 75, 3004 (1953)

For Tdurden969

Journal of Applied Electrochemistry 28, 1147-1151, 1998

I can email the articles to the bees in question (assuming I'm provided with email addresses); however, if you'd be so kind Rhodium smile , I'd really appreciate it if I could email you all the above for hosting purposes, which would also make them available to all others who are interested.

A bonus article for anyone else having access to trifluoroacetic anhydride coupled with an unhealthy interest in Friedel Crafts acylations; the article in question having been referred to in both Post 406009 (Assholium: "пропиофеноны со всеми вытекающими", Russian HyperLab) and Post 403374 (bottleneck: "A 'regenerable' Friedel-Crafts acylation catalyst", Novel Discourse).

To stir up a little interest I should perhaps mention this is one of the few methods allowing the acylation of benzodioxole without causing significant demethyleneation/decomposition; therefore it could be rather useful for the synthesis of the otherwise elusive 3,4-methylenedioxypropiophenone, the only real hurdle in an otherwise facile preparation of that Holy Grail of cathinones, Methylone.

Edit: Here's the title and reference for the above article:

Toward a Clean Alternative to Friedel-Crafts Acylation: In Situ Formation, Observation, and Reaction of an Acyl Bis(trifluoroacetyl)phosphate and Related Structures

J. Org. Chem. 1998, 63, 8946-8951

Edit 2: Ahh, Rhodium! But then, you've done a much better job than I. Thanks for hosting the remaining articles. smile

Rhodium
(Chief Bee)
07-29-03 21:29
No 450602
User Picture       Retrieved refs

Kinetic: It seems like we partially did the same job at the same time, but email me the rest of the articles at rhodium@rhodium.ws and I'll host them.

Java: Already posted in Post 429595 (Rhodium: "MMAI reference", Chemistry Discourse)

For Tdurden969:

Electrosynthesis attempts of tetrahydridoborates
E. L. Gyenge & C. W. Oloman
Journal of Applied Electrochemistry 28(10), 1147-1151 (1998) (https://www.rhodium.ws/pdf/borohydride.electrosynth.pdf)

For Chimimanie:

The Preparation of Alkyl Chlorides
James F. Norris, Hazel B. Taylor
J. Am. Chem. Soc. 46(3), 753-757 (1924) (https://www.rhodium.ws/pdf/alcohols2halides.hcl-zncl2.pdf)

Experimental from JACS 75, 3004 (1953)

2,5-Dimethoxyphenethyl alcohol
n-Butyllithium was prepared from lithium (28g) and n-butyl chloride (180g) in dry ether (350 ml.). A solution of hydroquinone dimethyl ether (205g) in dry ether (776mL) was added in one portion and the solution allowed to stand for 15 hours. The reaction mixture was maintained at 0°C while ethylene oxide (130g) was passed in as a gas during 3 hours. After standing overnight the reaction mixture was poured into ice-water (2 liters). The organic layer was separated, dried and fractionated. There was obtained 182g (68%) of product, bp 130-142°C/0.7mmHg, n25D 1.5402.
This alcohol formed a p-nitrobenzoate which melted at 73-74°C. From the distillation residue (20g) 6g of a crystalline by-product, mp 134-135°C, was isolated.

2,5-Dimethoxyphenethyl Bromide
A solution of 2,5-Dimethoxyphenethyl alcohol (66g) in benzene (65 ml) was stirred and cooled in an ice-bath while phosphorus tribromide (30g) in benzene (50 ml) was added dropwise. The solution was kept at 0-5°C for two hours and then at 60°C for four hours. Ice-water was added to the cool reaction mixture and the organic layer was separated. The benzene solution of crude bromide was washed with ice-cold 5% sodium hydroxide solution, water and dilute hydrochloric acid. Acidification of the sodium hydroxide extract yielded about 20g of an oil containing phenolic by-products. The benzene solution was concentrated and the residual crude bromide distilled rather quickly at a low pressure and temperature. There was obtained 48g (54%) of 2,5-Dimethoxyphenethyl Bromide, bp 97-110°C/0.25mmHg, n24D 1.5542. There is decomposition of this bromide with distillation and in three separate attempts an analytically pure sample could not be prepared, some loss of hydrogen bromide took place even with evaporative distillation.

Rhodium
(Chief Bee)
07-30-03 02:21
No 450647
User Picture       References fetched by Kinetic

Very interesting reference found by Kinetic:

Toward a Clean Alternative to Friedel-Crafts Acylation: In Situ Formation, Observation, and Reaction of an Acyl Bis(trifluoroacetyl)phosphate and Related Structures
J. Org. Chem. 63, 8946-8951 (1988) (https://www.rhodium.ws/pdf/f-c.acylation.clean.alternative.pdf)

For Chimimanie, fetched by Kinetic:

Selective deprotection of esters using magnesium and methanol
Tet. Lett. 35(34), 6207-6210 (1994) (https://www.rhodium.ws/pdf/ester.deprotection.mg-meoh.pdf)
DOI:10.1016/S0040-4039(00)73392-2

Potter
(HyperLab Bee)
07-31-03 08:13
No 450844
      Wanted references

Tetrahedron 6(¹2), 145-147 (1959)
4-methoxyphenol (19g) (4-methoxyphenoxy)-allyl ether (22.5g) 2-hydroxy-5-methoxy-allylbenzene (17.6g)
Yield 70% (different from Psycho Chemist's synth)

J. Pharm. Sci 58 (¹9), 1157-1159 (1969)
3,5-(MeO)₂-4-HO-Ph-COCl + CH₂N₂ 3,5-(MeO)₂-4-HO-Ph-CH₂CONH₂ + LAH Homosyringylamine

Rhodium
(Chief Bee)
07-31-03 11:02
No 450867
User Picture       For Chimimanie:

Synthesis and some properties of 1,2-dihydro-4,7-dihydroxycyclobuta{b}naphthalene-3,8-dione and 1,2,5,6-tetrahydro-4,7-dihydroxydicyclobuta{b,g}naphthalene-3,8-dione.
Watabe, Takashi; Oda, Masaji
Chemistry Letters (1984),   (10), 1791-4. (https://www.rhodium.ws/djvu/dihydrobenzocyclobutene.djvu)

Chimimanie
(Hive Bee)
08-01-03 11:08
No 451028
User Picture       DMT stuff

OK, those two refs are wanted: smile

Preparation and reduction of 3-indolyl aminomethyl ketones.    Bodendorf, K.; Walk, A. Tech. Hochschule Karlsruhe, Germany. Arch. Pharm. (1961), 294 484-7. Journal language unavailable. CAN 56:12913 AN 1962:12913 CAPLUS

and, more important:

Local anesthetically and antiarrythmically effective indoles and indoline derivatives, I. Synthesis of 1-, 2-, and 3-(aminoacetyl)indoles and 1-(aminoacetyl)indolines.    Mutschler, Ernst; Winkler, Werner. Pharmakol. Inst., Johann Wolfgang Goethe-Univ., Frankfurt/Main, Fed. Rep. Ger. Archiv der Pharmazie (Weinheim, Germany) (1978), 311(3), 248-55. CODEN: ARPMAS ISSN: 0365-6233. Journal written in German. CAN 89:24081 AN 1978:424081 CAPLUS

Those ref are useful for the acetyl indole -> DMT reaction

The second one look particulary excellent: that reaction is mentioned there:

indole ----1. chloroacetyl chloride----> keto DET 70% yield
2. diethylamine

and guess what give keto DET with twice its weight of NaBH4 in propanol wink

azole
(One Remarkable HyperLab Bee)
08-01-03 12:35
No 451038
      for Chimimanie

Darstellung und Reduktion von Indolyl-(3)-aminomethylketonen.
K.Bodendorf, A.Walk,
Arch. Pharm. (1961), 294 484-7 (http://hyperlab.bravepages.com/bodendorf.djvu)

(Our library is closed, so I shall be able to retrieve the second article only on Monday.)

Rhodium
(Chief Bee)
08-01-03 22:19
No 451127
User Picture       Fetched by FreakyDMT

10% Pd/C and HCOOH transfer hydrogenolysis of common protection groups
Indian journal of chemistry. Section B, 41(5):1064-1067 (2002) (https://www.rhodium.ws/pdf/cth.protecting.group.removal.pdf)

Vitus_Verdegast
(Hive Bee)
08-03-03 20:12
No 451475
User Picture       recent pharmacological review of MDMA

The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, "Ecstasy")
A. RICHARD GREEN, ANNIS O. MECHAN, J. MARTIN ELLIOTT, ESTHER O'SHEA, M. ISABEL COLADO

Pharmacol Rev 2003 : 5533-0
DOI:10.1124/pr.55.3.3

(fresh from the press, only a couple of weeks old!)

A Dream Within A Dream (http://www.poedecoder.com/Qrisse/works/dreamw.html)

GC_MS
(Hive Addict)
08-03-03 20:22
No 451478
User Picture       Pharmacol Rev

The DOI number doesn't work yet. I guess it will be working once the publisher has put the PDF online, since that hasn't happened yet. The publisher's website mentions the article for the Pharmacol Rev 55(3) issue, which is bound to appear in september of this year. However, an online PDF version is still not published. I guess you'll need a little bit more patience, my friend wink .

Dirty old man

ChemisTris
(Hive Bee)
08-03-03 21:15
No 451495
User Picture       Vitus...

The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, "Ecstasy")

PDF: http://mishmashblue.tripod.com/pr.55.3.3v1.pdf

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

GC_MS
(Hive Addict)
08-03-03 21:19
No 451496
User Picture       ? ? ? :-S :-S :-o But the doi still gives me...

? ? ?

crazy crazy blush

But the doi still gives me an error though.

Dirty old man

java
(Hive Bee)
08-08-03 03:29
No 452392
      Arylation of Carbanions

In the synthesis of Phenylacetone via enols and benzyl halides this articles discuss the methods ......java

Arylation of several carbanions by the SRN1 mechanism
Roberto A. Rossi and J. F. Bunnett
Journal of Organic Chemistry ,38,(17),pp 3020 - 3025,1973
SRN1 phenylation of nitrile carbanions and ensuing reactions. New route to alkylbenzenes
J. F. Bunnett and Bernhard F. Gloor
Journal of Organic chemistry, 38(24),pp 4156 - 4163, 1973
Mesitylation and phenylation of picolyl anions by the SRN1 mechanism
J. F. Bunnett and Bernhard F. Gloor
Journal of Organic chemistry, 39(3), pp 382 - 384, 1974

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Chimimanie
(Hive Bee)
08-12-03 05:28
No 453079
User Picture       Pharmacology

Standridge, Robert T.; Howell, Henry G.; Tilson, Hugh A.; Chamberlain, John H.; Holava, Henry M.; Gylys, Jonas A.; Partyka, Richard A.; Shulgin, Alexander T. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. Journal of Medicinal Chemistry (1980), 23(2), 154-62. CODEN: JMCMAR ISSN:0022-2623. CAN 92:76001 AN 1980:76001 CAPLUS
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1980/23/i02/pdf/jm00176a010.pdf

Iodination of dimethoxy compound, especially 2,5 dmb-butanamine

Braun, Ulrich; Shulgin, Alexander T.; Braun, Gisela; Sargent, Thornton, III. Synthesis and body distribution of several iodine-131-labeled central nervous system active drugs.   Journal of Medicinal Chemistry (1977), 20(12), 1543-6. CODEN: JMCMAR ISSN:0022-2623. CAN 87:193527 AN 1977:593527 CAPLUS
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1977/20/i12/pdf/jm00222a001.pdf

Butanamine analogs - comparaison between the various 4 subst analogs... Much wanted

Dowd, Cynthia S.; Herrick-Davis, Katharine; Egan, Christina; DuPre, Ann; Smith, Carol; Teitler, Milt; Glennon, Richard A. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A Partial Agonists. Journal of Medicinal Chemistry (2000), 43(16), 3074-3084. CODEN: JMCMAR ISSN:0022-2623. CAN 133:202582 AN 2000:473183 CAPLUS
DOI:10.1021/jm9906062

SAR of 5-ht2 ligand - Apparently we had it wrong, lets see that

EDIT: allready posted by Rhodium, (thank azole smile ), translation would bee nice smile
Synthesis of novel (phenylalkyl)amines for the investigation of structure - activity relationships. Part 1. Mescaline derivatives.    Trachsel, Daniel. Bubendorf, Switz.   Helvetica Chimica Acta (2002), 85(9), 3019-3026. CODEN: HCACAV ISSN: 0018-019X. Journal written in German. CAN 138:237572 AN 2002:805649 CAPLUS

The synthesis and the spectroscopic data of 14 novel 4-substituted mescaline derivs. are reported. Starting from syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde), several ethers were obtained from reaction with a series of corresponding satd. and unsatd. alkyl- and fluoroalkyl halides. Henry-reaction with MeNO2 or EtNO2 followed to afford the nitro-olefins, which were then reduced with AlH3 to the desired 2-phenylethyl- and 1-methyl-2-phenylethylamine derivs.

Post 423427 (Rhodium: "Synthesis of Novel Mescaline Derivatives (German)", Novel Discourse)

Rhodium
(Chief Bee)
08-12-03 14:15
No 453107
User Picture       Stuff 4 Java & Chimimanie

For Java: Your SNR1 arylation articles retrieved by Kinetic can be found here:

Arylation of several carbanions by the SRN1 mechanism
Roberto A. Rossi and J. F. Bunnett
Journal of Organic Chemistry ,38,(17),pp 3020-3025 (1973) (https://www.rhodium.ws/pdf/srn1.arylation-4.pdf)

SRN1 phenylation of nitrile carbanions and ensuing reactions. New route to alkylbenzenes
J. F. Bunnett and Bernhard F. Gloor
Journal of Organic chemistry, 38(24),pp 4156-4163 (1973) (https://www.rhodium.ws/pdf/srn1.arylation-5.pdf)

Mesitylation and phenylation of picolyl anions by the SRN1 mechanism
J. F. Bunnett and Bernhard F. Gloor
Journal of Organic chemistry, 39(3), pp 382-384 (1974) (https://www.rhodium.ws/pdf/srn1.arylation-6.pdf)

For Chimimanie:

Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes.
Standridge, Robert T.; Howell, Henry G.; Tilson, Hugh A.; Chamberlain, John H.; Holava, Henry M.; Gylys, Jonas A.; Partyka, Richard A.; Shulgin, Alexander T.
Journal of Medicinal Chemistry (1980), 23(2), 154-62. (https://www.rhodium.ws/pdf/shulgin.2-amino-1-phenylbutanes.pdf)

Synthesis and body distribution of several iodine-131-labeled central nervous system active drugs.
Braun, Ulrich; Shulgin, Alexander T.; Braun, Gisela; Sargent, Thornton, III.
Journal of Medicinal Chemistry (1977), 20(12), 1543-6. (https://www.rhodium.ws/pdf/shulgin.iodinated.peas.pdf)

1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A Partial Agonists
Cynthia S. Dowd, Katharine Herrick-Davis, Christina Egan, Ann DuPre, Carol Smith, Milt Teitler, and Richard A. Glennon
J. Med. Chem. 43(16) pp 3074 - 3084 (2000) (https://www.rhodium.ws/pdf/glennon.partial.agonists.pdf)
DOI:10.1021/jm9906062

Iodine-125 labeled 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane: an iodinated radioligand that specifically labels the agonist high-affinity state of 5-HT₂ serotonin receptors
Richard A. Glennon, Mark R. Seggel, William H. Soine, Katherine Herrick-Davis, Robert A. Lyon, Milt Titeler
J. Med. Chem. 31(1), 5-7 (1988) (https://www.rhodium.ws/pdf/glennon.doi-125.pdf)

Rhodium
(Chief Bee)
08-12-03 17:33
No 453131
User Picture       For ChemisTris: Nice novel asarone synthesis

For ChemisTris, scanned by Java:

New synthetic route for the preparation of potentially hypocholesterolemic analogs of alpha-asarone.
Determination of E/Z isomer content in natural and synthetic mixtures of alpha-asarone and its analogs.
Munoz, Heber; Diaz, Francisco; Sanchez, Adrian; Barajas, Marcelino; Labarrios, Fernando; Tamariz, Joaquin.
Acta Mexicana de Ciencia y Tecnologia, 11(41), 51-62 (1993) (https://www.rhodium.ws/pdf/asarone.nueva.ruta.pdf)

Abstract

A new and improved synthesis of potentially hypocholesterolemic (E)-2,4,5-R(MeO)₂C₆H₂CH=CHMe [I, R = NO₂, NH₂] from eugenol is described. This pathway also allows the prepn. of the 2-propenyl analogs. Moreover, 5,6-dimethoxy-2-methylindole was also prepd. efficiently by this method. -Asarone and (Z)-I [R = NO₂] were also prepd. and the isomer ratios in natural and synthetic samples of -asarone and I [R = NO₂] detd. by GC/MS.

Rhodium
(Chief Bee)
08-16-03 18:28
No 453943
User Picture       Propenylbenzene > Epoxide > DL-Ephedrine

The following citation was originally posted in Post 290749 (foxy2: "Novel route to Ephedrine and possibly its analogs", Novel Discourse)

Reactions of aliphatic epoxy compounds. IV. New route for DL-ephedrine synthesis.
Lunge, Jerzy; Belzecki, Czeslaw
Acta Polon. Pharm. 18, 177-81 (1961)

Rhodium
(Chief Bee)
08-18-03 00:42
No 454220
User Picture       Propenylbenzene to Ephedrine

This citation was originally posted in Post 290749 (foxy2: "Novel route to Ephedrine and possibly its analogs", Novel Discourse)

Reactions of aliphatic epoxy compounds. IV. New route for DL-ephedrine synthesis.
Lunge, Jerzy; Belzecki, Czeslaw
Acta Polon. Pharm. 18, 177-81 (1961)

Chimimanie
(Hive Bee)
08-18-03 17:35
No 454381
User Picture       Wanted refs

Methoxyamphetamines and fenfluramine compared to amphetamine for antagonism of electroshock seizures
Davis, W. Marvin; Hatoum, Hind T.; Hatoum, Nabil S.
Research Communications in Substances of Abuse (1982), 3(3), 297-305.
____ ___ __ _

Synthesis of Ar-S-R from Ar-Br with Cu²⁺

New synthetic method for 2,5-dimethoxybenzaldehyde.
Chen, Zhi-tao; Xiang, Jian-nan; Li, Zhi-liang.
Chongqing Daxue Xuebao, Ziran Kexueban (2002), 25(2), 109-111.
CODEN: CDXZF2 ISSN: 1000-582X. Journal written in Chinese. CAN 138:73048 AN 2002:335010

Abstract
Reimer-Tiemann reaction and a methoxylation through di-Me sulfate are employed for the prepn. of 2,5-dimethoxybenzaldehyde from p-methoxyphenol in this paper. Comparing different phase transfer catalysts, it can be demonstrated that the PEG-10000 is the most favorable catalyst used in Reimer-Tiemann reaction. The yield and quality are improved through the methoxylation of 2-hydroxy-5-methoxy-benzaldehyde in a buffer soln. The diverse factors influencing the yield are examd. Some explanations are given from theor. viewpoint. The proper exptl. conditions are found and the overall yield reached 68%.

Rhodium
(Chief Bee)
08-18-03 20:38
No 454408
User Picture       For Chimimanie:

You only wanted the first paper in this series, but you'll get the second part as a bonus wink

Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butane
Robert T. Standridge, Henry G. Howell, Jonas A. Gylys, Richard A. Partyka, Alexander T. Shulgin
J. Med. Chem. 19(12), 1400-1404 (1976) (https://www.rhodium.ws/pdf/shulgin/shulgin.4c-dom.pdf)

Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes
Robert T. Standridge, Henry G. Howell, Hugh A. Tilson, John H. Chamberlain, Henry M. Holava, Jonas A. Gylys, Richard A. Partyka, Alexander T. Shulgin
J. Med. Chem. 23(2), 154-162 (1980) (https://www.rhodium.ws/pdf/shulgin/shulgin.nuclear.substituted.2-amino-1-phenylbutanes.pdf)

7is
(Stranger)
08-20-03 13:04
No 454698
      Foxy, a designer tryptamine hallucinogen

Foxy, a designer tryptamine hallucinogen
Journal Of Analytical Toxicology 27(5), 313-317 (2003)

Edit: Retrieved and posted in Post 454743 (Lego: "Case Report: 5-MeO-DIPT", Tryptamine Chemistry)

Rhodium
(Chief Bee)
08-21-03 11:46
No 454843
User Picture       Retrieved refs

For Potter, retrieved by Lugh:

Peyote Alkaloids IX:
Identification and Synthesis of 3-Demethylmescaline, a Plausible Intermediate in the Biosynthesis of the Cactus Alcaloids
G,J, Kapadia, Y. N. Vaishnav, M. B. E. Fayez
J. Pharm. Sci. 58(9), 1157-1159 (1969) (https://www.rhodium.ws/djvu/kapadia.djvu)

Your requested Tetrahedron 6, 145-147 (1959) article can be found in Post 454844 (Rhodium: "4-Methoxyphenol -> 2-EtO-5-MeO-allylbenzene", Methods Discourse)

For Sonson, retrieved by Lugh:
The stereoisomers of 4-Methylaminorex
R. F. Klein, A.R. Sperling, D. A. Cooper, T. C. Kram
Journal of Forensic Sciences 34(4), 962-979 (1989) (https://www.rhodium.ws/djvu/cooper.djvu)

pHarmacist
(pHantasticant)
08-30-03 00:38
No 456424
User Picture       For Chimimanie (not requested on hive, elsewhere)

Analogs of amphetamine. 6. 2,5-Dimethoxy-4-methyl- and 2,5-dimethoxy-.alpha.,4-dimethylphenylalanines
Beng T. Ho, L. Wayne Tansey, Jen-Tzaw Huang;
J. Med. Chem.; 1971; 14(11); 1132-1133 (http://pharmacist.the-hive.tripod.com/alal-amphet.pdf)

2,5-Dimethoxy-4-methylphenylalanine
Roger M. Pinder, Keith Brewster;
J. Med. Chem.; 1971; 14(7); 650-651 (http://pharmacist.the-hive.tripod.com/25dimeo4me.pdf)

Dihydroxynitrobenzaldehydes and hydroxymethoxynitrobenzaldehydes: synthesis and biological activity as catechol-O-methyltransferase inhibitors
Rosa A. Perez, Eldiberto Fernandez-Alvarez, Ofelia Nieto, F. Javier Piedrafita;
J. Med. Chem.; 1992; 35(24); 4584-4588 (http://pharmacist.the-hive.tripod.com/benzald.pdf)

Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butane
Robert T. Standridge, Henry G. Howell, Jonas A. Gylys, Richard A. Partyka, Alexander T. Shulgin;
J. Med. Chem.; 1976; 19(12); 1400-1404 (http://pharmacist.the-hive.tripod.com/Phenylalk.pdf)

Chimimanie, remember that tripod is providing limited traffic. Meaning limited number of mb/hours.

Point... Counter Point...

Tdurden969
(Hive Bee)
09-04-03 04:39
No 457114
      synthesis of benzaldehyde

Water Science and Technology Vol 34 No 10 pp 113–120 © IWA Publishing 1996
A study on wastewater minimization in indirect electrochemical synthesis of benzaldehyde
Ding Zhou, Zhirong Sun and Wanli Hu

Department of Applied Chemistry, Harbin Institute of Technology Harbin, 15001 China

ABSTRACT:
Development of methods of pollution prevention is a strategic orientation for environmental protection. This paper describes studies on waste minimization in benzaldehyde production by using indirect electrochemical oxidation of toluene instead of the seriously polluting traditional chemical process. The new technology developed eliminates the discharge of wastewater by recycling the reactive solution and gives a higher yield of benzaldehyde

==========================================

Journal of Applied Electrochemistry 33 (3/4)   p.273-277 March 4, 2003 Kluwer

A new approach to electrochemical production of benzaldehyde from toluene in an undivided cell in the presence of the couple V5+/V4+
Qingfeng Y.1 Xiaoping L.2 and Xiuling Z.2

Abstract:

Oxidation of toluene to benzaldehyde in the presence of the redox couple V5+/V4+ was carried out in an undivided cell where oxygen gas was continuously bubbled over the cathodic surface and the electrolyte was a mixture of aqueous H2SO4 solution containing V5+ and toluene. Some experimental conditions affecting the current efficiency for benzaldehyde production, such as H2SO4 concentration, current density, V5+ concentration and surfactants, were determined. The maximum current efficiency for benzaldehyde production at ambient temperature was 156.3% under the conditions of 11 M H2SO4, 2.7 Ч 10−4 M CTAB, current density 1.25 mA cm−2 and 0.0128 M V5+.

Thanks

Potter
(HyperLab Bee)
09-05-03 06:35
No 457290
      synth P2P

Liebigs Ann. Chem. 654, 92-111 (1962)

PhC(O)CH3 + CH2N2 --> P2P
Kt=AlCl3 yield 50%

Rhodium
(Chief Bee)
09-09-03 00:54
No 457806
User Picture       Retrieved References

For Tdurden969:

A new approach to electrochemical production of benzaldehyde from toluene in an undivided cell in the presence of the couple V⁵⁺/V⁴⁺
Qingfeng Y., Xiaoping L., Xiuling Z.
Journal of Applied Electrochemistry 33(3/4), 273-277 (2003) (https://www.rhodium.ws/pdf/toluene2ba.vanadium.electro-ox.pdf)

A study on wastewater minimization in indirect electrochemical synthesis of benzaldehyde
Ding Zhoua, Zhirong Suna and Wanli Hu
Water Science and Technology 34(10), 113-120 (1996) (https://www.rhodium.ws/pdf/toluene2ba.manganese.electro-ox.pdf)
DOI:10.1016/S0273-1223(96)00704-4

Rhodium
(Chief Bee)
09-09-03 15:41
No 457914
User Picture       Wanted: Safrole Microwave Isomerization

Isomerization of some allylbenzenes in a microwave batch reactor
Le, Ngoc Thach; Strauss, Christopher R.
Tap Chi Hoa Hoc 38(1), 76-79 (2000)
(In English) ISSN: 0378-2336 CAN 134:87870 AN 2000:577146

Abstract

In this paper we present a study of the isomerization of some allylbenzenes such as allylbenzene, eugenol, methylchavicol, and safrole. It is the first time this reaction take place in a microwave batch reactor in aq. acid(sulfuric). High yields of 1-propenylbenzene were obtained from allylbenzene after short reaction times.

Ref found in Post 291995 (foxy2: "Safrole Isomerization in microwave", Chemistry Discourse)

ChemisTris
(Hive Bee)
09-10-03 06:32
No 458085
User Picture       Vitus: Br. J. Pharmacol., Jun 2002; 136: 510 - 519

Full text PDF: smile

Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT_2A and 5-HT_2C receptors
Claudio Acuña-Castillo, Claudio Villalobos, Pablo R. Moya, Patricio Sáez, Bruce K. Cassels, and J. Pablo Huidobro-Toro
British Journal of Pharmacology 136, 510-519 (2002) (http://www.bomber.co.nz/bjp/510.pdf)

Abstract: Post 457936 (Vitus_Verdegast: "potency and efficacy of subst. PEAs at 5HT2A/2C", General Discourse)

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

pHarmacist
(pHantasticant)
09-10-03 10:36
No 458146
User Picture       Wanted

Nichols. D. E. J. Theor. Biol. 1976. 59. 167.

Very interesting request there Vitus, also thanks ChemisTris! smile

Point... Counter Point...

ChemisTris
(Hive Bee)
09-15-03 03:34
No 459118
User Picture       Progress toward the total synthesis of salvinorin

_{This is from the 225th ACS National Meeting. I hope that someone can post more about it. As far as i can tell, it is not yet available through http://www.cas.org/Support/dds.html}

Progress toward the total synthesis of salvinorin A: A potent, non-nitrogenous κ-opioid receptor selective agonist.
Vangapandu, Suryanarayana; Phillip, Ashok; Stewart, Jeremy D.; Zjawiony, Jordan; Avery, Mitchell A.; McCurdy, Christopher R.
_{Department of Medicinal Chemistry, University of Mississippi, University, MS, USA.}
Abstracts of Papers, 225th ACS National Meeting, New Orleans, LA, United States, March 23-27, 2003 ORGN-421.
_{Publisher: American Chemical Society, Washington, D. C CODEN: 69DSA4 Conference; Meeting Abstract AN 2003:184914

Abstract
Salvinorin A (1), a nonnitrogenous, neoclarodane diterpine, obtained from Salvia divinorum, has been reported to be the most potent naturally occurring hallucinogen, with an ED in humans in the 200-1000 µg range when smoked with a typical duration of action being several minutes to an hour. Salvia divinorum exts. and salvinorin A have become widely used in the U.S. as legal hallucinogens. The site of pharmacological activity remained a mystery until the recent report that identified salvinorin A as a potent and selective ligand for the κ-opioid receptor. Thus representing a unique structural class of nonnitrogenous opioid ligands. In order to investigate structure-activity relationships of salvinorin A, analogs must be made. One approach to analog synthesis is from a total synthesis perspective. To our knowledge, there are no known syntheses of salvinorin A. Here we report our progress toward the first total synthesis of salvinorin A.}

Got democracy?http://www.dhushara.com/book/multinet/democ/wed.htm

java
(Hive Bee)
09-17-03 02:16
No 459496
      Facile Synthesis of Methanesulonate Esters

Facile Synthesis of Methanesulfonate Esters
Ronald K. Crossland and Kenneth L. Servis

[b]Journal of Organic Chemistry(JOC), V 35, 1970, pages 3195-6.[/b

Edit : by java (9-17-03), noted that the article has been posted already by Aurelius, thank you for pointing it out to me Rhodium

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
09-17-03 09:50
No 459580
User Picture       Methanesulfonate synthesis

Java: That article has already been posted - Post 433077 (Aurelius: "Methanesulfonate esters JOC 35(9), 3195-6 (1970)", Methods Discourse)

Rhodium
(Chief Bee)
09-19-03 14:14
No 459956
User Picture       For Potter: Acetophenone to Phenylacetone

For Potter:

Katalysierte Homologisierung Cycloaliphatischer und Aliphatischer Ketone mit Diazoalkanen
Eugen Müller, Martin Bauer
Ann. Chem. 654, 92-111 (1962) (https://www.rhodium.ws/pdf/diazomethane.ketone.homologation.pdf)

PhCOCH₃ + CH₂N₂ --AlCl₃--> P2P (50%)

Lego
(Hive Bee)
09-19-03 15:11
No 459964
User Picture       Anal. Bioanal. Chem., 2003, 376(8),1212-24

As mentioned: Post 459376 (Lilienthal: "Anal Bioanal Chem. 2003 Aug; 376(8):1212-24.", General Discourse)

Anal Bioanal Chem. 2003 Aug; 376(8):1212-24. Epub 2003 Jul 04

Laboratory and field experiments used to identify Canis lupus var. familiaris active odor signature chemicals from drugs, explosives, and humans.
Lorenzo N, Wan T, Harper RJ, Hsu YL, Chow M, Rose S, Furton KG.
Medline (PMID=12845400)
DOI:10.1007/s00216-003-2018-78 (The DOI is not working although Springer gives this it)

Can somebee post this article in the above thread?
Thanks! smile

Edit: The correct DOI:10.1007/s00216-003-2018-7 /Rhodium

The candle that burns twice as bright burns half as long

Rhodium
(Chief Bee)
09-21-03 01:47
No 460171
User Picture       Lab Prep of Trifluoroacetic Anhydride

Trifluoroacetic Acid + Phosphorus Pentoxide Trifluoroacetic Anhydride
Swarts, F.
Bull. Acad. Roy. Belg. 8, 343 (1922)

pHarmacist
(pHantasticant)
09-21-03 11:40
No 460224
User Picture       The Grandberg synthesis

Basicly tryptamines from 4-halobutanals but in which the nitrogen that is usually lost during the Fischer process is instead incorporated as the nitrogen of aminoethyl side-chain - straight to tryptamine that is. A synthetic beauty, the inventor (Grandberg) must bee really proud of his method extraordinare...

Grandberg, I. I., Chem. Heterocycl. Compd. (engl. Transl.) 1974, 10, 501.

Something like this:

http://www.bassdrive.com/BassDrive.m3u

GC_MS
(Hive Addict)
09-21-03 19:45
No 460260
User Picture       NaBH4 reduction of aryl alkyl ketones

Two references I found in Post 460118 (Rhodium: "Enhancing NaBH4 Reactivity & Selectivity", Novel Discourse):

A Ono, T Maruyama, N Suzuki. Synth Commun 17 (1987) 1001

[...] The NaBH4 in combination with anhydrous AlCl3 conveniently reduces diaryl and aryl alkyl ketones to methylenic hydrocarbons. [...]

CF Nutaitis, JE Bernardo. Synth Commun 20 (1990) 487

Describes the reduction of substituted benzyl alcohol to their corresponding ethyl benzenes. Some gems might be created via this method.

Advanced clitoris massage specialist. 32 years of experience. PM me for a "sample".

Rhodium
(Chief Bee)
10-01-03 19:41
No 462120
User Picture       Retrieved References

All the files below has been retrieved and scanned by lugh:

For GC_MS:
A Ono, T Maruyama, N Suzuki. Synth Commun 17 (1987) 1001
CF Nutaitis, JE Bernardo. Synth Commun 20 (1990) 487
Has been linked in Post 462116 (Rhodium: "NaBH4 Deoxygenation of Benzyl Ketones/Alcohols", Novel Discourse)
Synth Commun 32(17) (2002) 2677-2681
Has been linked in Post 461804 (GC_MS: "Urea-Hydrogen peroxide complex", Novel Discourse)

For pHarmacist:
Indolylalkylamines From Arylhydrazines and gamma- and delta-Halocarbonyl Compounds (Review)
Grandberg, I. I.
Chem. Heterocycl. Compd. (engl. Transl.) 1974, 10, 501. (https://www.rhodium.ws/djvu/grundberg.djvu)

Structural Correlation between Apomorphine and LSD:
Involvement of Dopamine as well as Serotonin in the Actions of Hallucinogen
Dave E. Nichols
J. Theor. Biol. 59, 167-177 (1976) (https://www.rhodium.ws/djvu/nichols.djvu)

Rhodium
(Chief Bee)
10-06-03 17:57
No 462997
User Picture       PCP Analogs

Edit: Found by chemistris: J.Fluorine. Chem. 114(1), 39-42 (2002) (https://www.rhodium.ws/pdf/pcp/syntheses.of.fluorinated.phencyclidine.analogs.pdf)

Rhodium
(Chief Bee)
10-11-03 04:13
No 463915
User Picture       GHBTolerance and Withdrawal in a Rat Model

Gamma-hydroxybutyric Acid Tolerance and Withdrawal in a Rat Model
Bania, T. C.; Ashar, T.; Press, G.; Carey, P. M.
Academic Emergency Medicine Acad Emerg Med 10(7), 697-704 (2003) (http://www.rhodium.ws/pdf/ghb.tolerance.withdrawal.model.pdf)
Medline (PMID=12837642)

Abstract

Long-term daily use of gamma-hydroxybutyrate (GHB) and related compounds has recently been associated with a withdrawal syndrome. To the best of the authors' knowledge, there are currently no animal models of GHB withdrawal. Objectives: The authors studied and described the effect of chronic dosing of GHB (3-6 days) on tolerance and withdrawal in a rat model. Methods: Rats were administered GHB every three hours via intraperitoneal catheter. Groups of rats (2 per group) were dosed with GHB for either 3 (24 doses), 4 (32 doses), 5 (40 doses), or 6 (48 doses) days. The GHB dose was 0.25 g/kg for doses 1-8, 0.75 g/kg for doses 9-12, 1 g/kg for doses 13-16, 1.25 g/kg for doses 17-24, 1.5 g/kg for doses 25-32, 1.75 g/kg for doses 33-40, and 2 g/kg for doses 41-48. Following the last dose of GHB, the rats were scored using a 16-point ethanol intoxication-withdrawal scale rating spontaneous behaviors, response to handling, grooming, and neurological signs. Lower scores indicate intoxication, while higher scores indicate withdrawal. Scores were recorded at hours 0, 1, 2, 3, 4, 5, 6, 9, 12, and 24. Results: Tolerance: Rats dosed with GHB for more days were less intoxicated one hour after their last GHB dose despite receiving higher doses. Withdrawal: The scores for all rats dosed with GHB increased at hours 4 (p = 0.028), 5 (p = 0.037), 6 (p = 0.007), and 9 (p = 0.024) after the last dose, indicating withdrawal. The scores demonstrated a linear increase dependent upon the number of days of GHB dosing at hours 3 (p < 0.000), 4 (p = 0.004), 5 (p = 0.002), and 12 (p = 0.039) as well as prior to the last dose at hour 0 (p = 0.000). No rats developed seizures. Conclusions: Tolerance and mild withdrawal in rats can be induced by administering intraperitoneal GHB every three hours for 3-6 days. More prolonged dosing and higher doses of GHB may be necessary to induce severe withdrawal.

Edit: Article retrieved by Ziqquratu: Academic Emergency Medicine Acad Emerg Med 10(7), 697-704 (2003) (http://www.rhodium.ws/pdf/ghb.tolerance.withdrawal.model.pdf)

imp
(Stranger)
10-17-03 05:50
No 465119
      An easy one

This should be quite easy, SWIM's library is missing the year!... Bull. soc. chim., pp.196, 1940

They claim to chloropropylate anisole, and dehydrohalogenate to get anethole. It might be applicable for 3,4-methylenedioxybenzene --> isosafrole. The paper also descibes 30% yield in chloroisobutylation of anisole and 40-60% yield for chloroethylation.

Rhodium
(Chief Bee)
10-23-03 17:12
No 466328
User Picture       Bromodecarbo*ylation with NaBr/Oxone

Bromodecarbonylation and Bromodecarboxylation of Electron-Rich Benzaldehydes and Benzoic Acids with Oxone^® and Sodium Bromide
Bon-Suk Koo; Eun-Hoo Kim; Kee-Jung Lee
Synthetic Communications 32(15), 2275-2286 (2002) (https://www.rhodium.ws/pdf/bromodecarbo_ylation.nabr-oxone.pdf)
DOI:10.1081/SCC-120005997

Abstract
Benzaldehydes and benzoic acids bearing ortho and para electron-donating substituents having unshared electron-pair have undergone bromodecarbonylation or bromodecarboxylation on treatment with sodium bromide in the presence of Oxone in aq. methanol.

GC_MS
(Hive Addict)
10-24-03 17:26
No 466540
User Picture       https://www.rhodium.ws/pdf/amanita.muscaria.rev...

https://www.rhodium.ws/pdf/amanita.muscaria.review.pdf

Advanced clitoris massage specialist. 32 years of experience. PM me for a "sample".

azole
(One Remarkable HyperLab Bee)
10-27-03 18:32
No 467048
      the only ref. on MMA human use

de Zorzi, C., Cavalli, A., Zacchia, 10, 3 (1974)

Journal info: Zacchia: archivio di medicina legale, sociale e criminologica
Roma, -, 1921- * Non pubbl. dal 1981 al 1982 * ISSN 0044-1570

_{The experiments on animals suggest that MMA (3-methoxy-4-methylamphetamine) can be considered as a non-neurotoxic analog of MDMA (https://www.rhodium.ws/pdf/mmai.pdf)

A quote from PiHKAL #123: (http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml)

Some years ago a report appeared in the forensic literature of Italy, of the seizure of a small semitransparent capsule containing 141 milligrams of a white powder that was stated to be a new hallucinogenic drug. This was shown to contain an analogue of DOM, 3-methoxy-4-methylamphetamine, or MMA. The Italian authorities made no mention of the net weight contained in each dosage unit, but it has been found that the active level of MMA in man is in the area of 40-60 milligrams. The compound can apparently be quite dysphoric, and long lived.

There are several questions that may be answered in this article:Are there anecdotal reports on the effects of MMA in humans?
How was the structure of the seized substance elucidated? Is there any possibility that it could be actually an isomer of MMA, say, 4-MeO-3-Me-A, PMMA, or 4-MeO-3,5-diMe-PEA?
What method was applied to synthesize the substance?}

Chimimanie
(Hive Bee)
10-28-03 01:23
No 467162
User Picture       2-amino-5-spiro substituted oxazoline-4-one

Synthesis of compounds with potential central nervous system stimulant activity. I. 2-Amino-2-oxazolin-4-one-5-spirocycloalkanes and 2-amino-2-oxazolin-4-one-5-spiro(4'-piperidines)
Michael R. Harnden and Ray R. Rasmussen
JMC 12 pp 919 - 921 (1969)
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1969/12/i05/pdf/jm00305a051.pdf

Synthesis of compounds with potential central nervous system stimulant activity. II. 5-Spiro-substituted 2-amino-2-oxazolines
Michael R. Harnden and Ray R. Rasmussen
JMC 13 pp 305 - 308 (1970)
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1970/13/i02/pdf/jm00296a039.pdf

see also Patent US3931198 column 14: one of those compound is stimulant at 0.1 mg/kg with a LD50 > 750 mg/kg in mice. What is this compound? I never heard of it!

moo
(Hive Bee)
10-28-03 02:10
No 467172
      Are you asking which compound it is in the...

Are you asking which compound it is in the patent? It's number 32. Here are the articles.

Synthesis of compounds with potential central nervous system stimulant activity. I.
2-Amino-2-oxazolin-4-one-5-spirocycloalkanes and 2-amino-2-oxazolin-4-one-5-spiro(4'-piperidines)
Michael R. Harnden, Ray R. Rasmussen
J. Med. Chem. 12, 919-921 (1969) (https://www.rhodium.ws/pdf/spiro-oxazolines-1.pdf)

Synthesis of compounds with potential central nervous system stimulant activity. II.
5-Spiro-substituted 2-amino-2-oxazolines
Michael R. Harnden, Ray R. Rasmussen
J. Med. Chem. 13, 305-308 (1970) (https://www.rhodium.ws/pdf/spiro-oxazolines-2.pdf)

_{fear fear hate hate}

Lego
(Hive Bee)
10-28-03 13:45
No 467258
User Picture       And another Synth. Comm. article

Thank you Rhodium for the PDF-version of the article!!! cool

But there is another article needed....

Alkylation of alkyl nitroacetates under PTC conditions.    Gogte, V. N.; Natu, A. A.; Pore, V. S. Natl. Chem. Lab., Pune, Italy.

Synthetic Communications (1987), 17(12), 1421-9.

CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 109:6178 AN 1988:406178 CAPLUS

Abstract

Treatment of O2NCHRCO2R1 (I; R = H, R1 = Me; R = Me, R1 = Et) with p-R2C6H4CH2Br (R2 = H, Cl, MeO) and KHCO3 in DMF contg. TEBA gave 70-78% p-R2C6H4CH2CR(NO2)CO2R1. Similar treatment of I (R = H, R1 = Me) with p-O2NC6H4CH2Br gave (p-NO2C6H4CH2)2C(NO2)CO2Me.

Edit: Oops, and another one wink

S-Oxidation products of alkylthioamphetamines.    Rezende, Marcos Caroli; Nunez, Christian; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Hurtado-Guzman, Claudio. Facultad de Quimica y Biologia, Universidad de Santiago de Chile, Santiago, Chile.

Synthetic Communications (2002), 32(17), 2741-2750

CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 138:237922 AN 2002:674846 CAPLUS

Abstract

The prepn. of the sulfoxides and the sulfones of two centrally active alkylthioamphetamine salts, (±)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride and (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane hydrochloride, is described.

The candle that burns twice as bright burns half as long

java
(Hive Bee)
10-28-03 16:49
No 467301
      Re; Synthetic Communications articles

Register here, http://www.dekker.com and you are granted a 2 minute look at the article for free .......I imagine any article in the list of journals they carry..............java

P.S. I tried copying but not able there must be some trick to get it, let me know if you figure it out, also you can only preview for 2 minute once per article, I thought I let you know so be ready to copy and read fast.

We're all in this world together,
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
10-28-03 17:02
No 467305
User Picture       Snagging Synthetic Communications Articles

You can right-click and save each frame of a normal length article in those two minutes if you're fast, or you can open each page in a new window. You will still become forwarded to a "Time's up!" page after 2 minutes, but the "back" key still works in each window.

But - unfortunately only year 2001, 2002 & 2003 are available online.

Rhodium
(Chief Bee)
10-29-03 13:33
No 467512
User Picture       Wanted Reference

Synthesis markers in illegally manufactured 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethamphetamine.
International Journal Of Legal Medicine 106(1), 19-23 (1993)

Lego
(Hive Bee)
10-29-03 13:57
No 467519
User Picture       Studies in Surface Science and Catalysis (1991)

Selective hydrogenation of aromatic and aliphatic nitro compounds by hydrogen transfer over magnesia.    Kijenski, J.; Glinski, M.; Wisniewski, R.; Murghani, S. Inst. Org. Technol., Warsaw Tech. Univ., Warsaw, Pol.

Studies in Surface Science and Catalysis (1991), 59(Heterog. Catal. Fine Chem. 2), 169-76.

CODEN: SSCTDM ISSN: 0167-2991. Journal written in English. CAN 115:182389 AN 1991:582389 CAPLUS

Abstract

The possibility of using aliph. alcs. as hydrogen donors for the catalytic transfer redn. of nitro group over MgO was examd. Catalytic hydrogen transfer was found to be effective and selective for redn. of nitrobenzene, 4-nitrotoluene, 4-chloronitrobenzene, 4-nitro-m-xylene, b-nitrostyrene, 3-nitrobenzaldehyde, 1-nitropropane, and 1-nitrobutane. Conversion of starting nitro compd. into desired product depended on the alc. used as a donor. Adsorption of reactant and catalyst deactivation were studied by ESR. New aspects of a role of one-electron donor sites in hydrogen transfer over MgO were demonstrated.

The candle that burns twice as bright burns half as long

Rhodium
(Chief Bee)
10-30-03 23:37
No 467885
User Picture       Structure-activity of piracetam-like compounds

2-Pyrrolidinone moiety is not critical for the cognition-enhancing activity of piracetam-like drugs
Serena Scapecchi, Cecilia Martellia, Carla Ghelardini, Luca Guandalini, Elisabetta Martini and Fulvio Gualtieria
Il Farmaco, 58(9), 715-722 (2003)
DOI:10.1016/S0014-827X(03)00111-3

Abstract
Following the indications of previous work, 2-pyrrolidinone moiety of piracetam and piracetam-like compounds has been opened to the corresponding amide derivatives. As found previously in the case of 1,4-diazabicyclo[4.3.0]nonan-9-one compounds, the cognition-enhancing activity of 2-pyrrolidinone compounds is maintained in most cases, suggesting that this moiety is not crucial for activity.

Edit: The file has been uploaded to (Thanks Lego & Ziqquratu)

Rhodium
(Chief Bee)
10-31-03 14:03
No 468001
User Picture       4-MTA & Aleph-2 for Lego

S-Oxidation products of alkylthioamphetamines
Rezende, Marcos Caroli; Nunez, Christian; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Hurtado-Guzman, Claudio.
Synthetic Communications 32(17), 2741-2750 (2002) (https://www.rhodium.ws/pdf/aleph-2.4-mta.pdf)

Abstract
The prepn. of the sulfoxides and the sulfones of two centrally active alkylthioamphetamine salts, (±)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride and (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane hydrochloride, is described.

Rhodium
(Chief Bee)
10-31-03 20:10
No 468022
User Picture       Chloropropylation/elimination of anisole

For Imp:

Chloropropylation/elimination of anisole -> Anethole
Bull. soc. chim., pp.196, (1940)

Post 468021 (Rhodium: "Styrene Derivatives by Aromatic Chloroalkylation", Novel Discourse)

pHarmacist
(pHantasticant)
11-05-03 12:24
No 468900
User Picture       Wanted

N.A. Zakharova, N.V. Khromov-Borisov, M.L. Indenbom, Several derivatives of p-chlorophenoxyacetic acid, Biol. Aktivn. Soedin. Akad. Nauk. SSSR (1965) 112–116; Chem. Abstr. 63 (1965) 17948a.

http://www.bassdrive.com/BassDrive.m3u

Chimimanie
(Hive Bee)
11-09-03 03:07
No 469708
User Picture       beta-Chloroethylamines related to mescaline

beta-Chloroethylamines related to mescaline.    Cooper, Paul D. Fac. Pharm., Univ. Montreal, Montreal, QC, Can. Journal of Medicinal Chemistry (1973), 16(9), 1057-9. CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 80:63 AN 1974:63 CAPLUS

http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1973/16/i09/pdf/jm00267a026.pdf

Abstract

beta-Chloromethylmescaline-HCl (I) [49557-34-8] (>40 mg/kg, i.p.) produced a twitch syndrome in mice characteristic of mescaline action. I may cyclize in vivo to an aziridine sterically resembling the psychotomimetic alpha-methylmescaline. However, N-(beta-chloroethyl)mescaline-HCl [15257-73-5], which may cyclize in vivo to an aziridine resembling the pharmacol. inactive N,N-dimethylmescaline, produced a periodic spasticity response qual. different from that due to I or mescaline. alpha-Chloromethylphenethylamine-HCl [49557-36-0] produced no response, indicating that the mescaline-like effect of I was due to its trimethoxyphenyl substituent and not to its potential as an alkylating agent. To synthesize I, 3,4,5-trimethoxybenzaldehyde [86-81-7] was condensed with diethyl malonate, and the product was hydrogenated over Pd/C and reacted with EtONO to form Et [2-oximino-3-(3,4,5-trimethoxyphenyl)]propionate [49557-37-1]; this was reduced to 3,4,5-trimethoxyphenylalaninol [49557-38-2], converted to the sulfate ester, and then to I.

Thanx smile

pHarmacist
(pHantasticant)
11-09-03 11:33
No 469777
User Picture       beta-Chloroethylamines Related to Mescaline

For Chimimanie:

beta-Chloroethylamines related to mescaline
Cooper, Paul D.
Journal of Medicinal Chemistry 16, 1057-9 (1973) (http://pharmacist.the-hive.tripod.com/meschalo.pdf)

Abstract
beta-Chloromethylmescaline-HCl (I) [49557-34-8] (>40 mg/kg, i.p.) produced a twitch syndrome in mice characteristic of mescaline action. I may cyclize in vivo to an aziridine sterically resembling the psychotomimetic alpha-methylmescaline. However, N-(beta-chloroethyl)mescaline-HCl [15257-73-5], which may cyclize in vivo to an aziridine resembling the pharmacol. inactive N,N-dimethylmescaline, produced a periodic spasticity response qual. different from that due to I or mescaline. alpha-Chloromethylphenethylamine-HCl [49557-36-0] produced no response, indicating that the mescaline-like effect of I was due to its trimethoxyphenyl substituent and not to its potential as an alkylating agent. To synthesize I, 3,4,5-trimethoxybenzaldehyde [86-81-7] was condensed with diethyl malonate, and the product was hydrogenated over Pd/C and reacted with EtONO to form Et [2-oximino-3-(3,4,5-trimethoxyphenyl)]propionate [49557-37-1]; this was reduced to 3,4,5-trimethoxyphenylalaninol [49557-38-2], converted to the sulfate ester, and then to I.

http://www.bassdrive.com/BassDrive.m3u

Lego
(Hive Bee)
11-09-03 15:48
No 469796
User Picture       And yet another Synth. Comm. article

Selective hydrogenation of aromatic and aliphatic nitro compounds by hydrogen transfer over magnesia
Kijenski, J.; Glinski, M.; Wisniewski, R.; Murghani, S.
Studies in Surface Science and Catalysis (1991), 59(Heterog. Catal. Fine Chem. 2), 169-76.
CODEN: SSCTDM ISSN: 0167-2991. Journal written in English. CAN 115:182389 AN 1991:582389 CAPLUS

Abstract
The possibility of using aliph. alcs. as hydrogen donors for the catalytic transfer redn. of nitro group over MgO was examd. Catalytic hydrogen transfer was found to be effective and selective for redn. of nitrobenzene, 4-nitrotoluene, 4-chloronitrobenzene, 4-nitro-m-xylene, b-nitrostyrene, 3-nitrobenzaldehyde, 1-nitropropane, and 1-nitrobutane. Conversion of starting nitro compd. into desired product depended on the alc. used as a donor. Adsorption of reactant and catalyst deactivation were studied by ESR. New aspects of a role of one-electron donor sites in hydrogen transfer over MgO were demonstrated.

The candle that burns twice as bright burns half as long

pHarmacist
(pHantasticant)
11-09-03 23:05
No 469872
User Picture       K. Gerwald, Chem. Ber. 99, 1002 (1966).

K. Gerwald, Chem. Ber. 99, 1002 (1966).

EDIT: It's about Diels-Alder route to precursors of anthranilic acid derivatives. More that that I don't know.

http://www.bassdrive.com/BassDrive.m3u

Rhodium
(Chief Bee)
11-10-03 00:30
No 469893
User Picture       ph: What's it about?

It is very appreciated if you post the title or an abstract of the article, so that people are encouraged to retrieve it not only as a service for you, but for their own sake too, should their interests be similar to yours.

azole
(One Remarkable HyperLab Bee)
11-11-03 10:59
No 470166
      Retrieved references

For Rhodium, as requested in Post 217986 (Rhodium: "Wanted references", Novel Discourse) :
Zakharkin et.al., Izv. Akad. Nauk SSSR Ser. Khim., 561 (1964) - see the translated article in Post 470158 (azole: "reductions with NaAlH4 in hydrocarbon media", Russian HyperLab)

For pHarmacist:
K. Gewald, Chem. Ber., 99, 1002 (1966)
The article can be downloaded here:

http://briefcase.yahoo.com
Login: hyperlab_storage
Password: yukhimik

...then follow the link "Your Briefcase address": http://briefcase.yahoo.com/hyperlab_storage to see the content of the root folder.

File: ChemBer99_1002.djvu

As to the article by N.A. Zakharova et al., Biol. Aktivn. Soedin. Akad. Nauk. SSSR (1965) 112–116,- I haven't found the journal, sorry.

pHarmacist
(pHantasticant)
11-11-03 14:19
No 470203
User Picture       Wanted

Several derivatives of p-chlorophenoxyacetic acid
N.A. Zakharova, N.V. Khromov-Borisov, M.L. Indenbom
Biol. Aktivn. Soedin. Akad. Nauk. SSSR 112–116 (1965)
Chem. Abstr. 63, 17948a (1965)

http://www.bassdrive.com/BassDrive.m3u

Chimimanie
(Hive Bee)
11-11-03 22:17
No 470283
User Picture       AMT, AET and 5-meo-derivat

Hi! smile

Does any of you have access to this italian journal? Farmaco, Ed. Sci

I wanna those 3 refs, authors are S. Pietra and G. Tacconi:

Farmaco, Ed. Sci 13 893 1958
Farmaco, Ed. Sci 14 854 1959
Farmaco, Ed. Sci 16 483 1961

Altough the abstract are detailed, the actual text would be better (but it is italian, damn frown ).

They describe this route:

Indigo --nitric acid--> Isatin --?acetone/MEK?--> Isatylideneacetone --Pd/C, STP, hydroxylamine--> the oxime --Na, boiling PrOH--> AMT/AET

To make AMT from indigo this easily without even passing through indole stage should be further researched. wink
(and the yields looks ok too) cool

Rhodium
(Chief Bee)
11-11-03 22:37
No 470286
User Picture       Chem. Pharm. Bull.

Pharmacist:

1. Chem. Pharm. Bull. 2002 is freely available online, see Post 434885 (Rhodium: "J-Stage Japanese Journals (Direct Links)", Novel Discourse)
2. What made you unable to search for the article in TFSE this time? wink I have already posted it in Post 298275 (Rhodium: "Psilosynth", Tryptamine Chemistry)

azole
(One Remarkable HyperLab Bee)
11-13-03 16:15
No 470667
      Retrieved references

For Rhodium, as requested in Post 217986 (Rhodium: "Wanted references", Novel Discourse) :
Zakharkin et.al., Izv. Akad. Nauk SSSR Ser. Khim., 561 (1964) - see the translated article in Post 470158 (azole: "reductions with NaAlH4 in hydrocarbon media", Russian HyperLab)

For pHarmacist:
Diels-Alder route to precursors of anthranilic acid derivatives
K. Gewald, Chem. Ber., 99, 1002 (1966)
The article can be downloaded here:

http://briefcase.yahoo.com
Login: hyperlab_storage
Password: yukhimik

...then follow the link "Your Briefcase address": http://briefcase.yahoo.com/hyperlab_storage to see the content of the root folder.

File: ChemBer99_1002.djvu

As to the article by N.A. Zakharova et al., Biol. Aktivn. Soedin. Akad. Nauk. SSSR (1965) 112–116,- I haven't found the journal, sorry.

For Chimimanie:
Il Farmaco, Ed. Sc., 14, 854-866 (1959). (http://hyperlab.0catch.com/Derivati_Indolici_IV.djvu)
Il Farmaco, Ed. Sc., 16, 483-491 (1961). (http://hyperlab.0catch.com/Derivati_Indolici_VI.djvu)

Bonus article:
Il Farmaco, Ed. Sc., 16, 492-501 (1961). (http://hyperlab.0catch.com/Derivati_Indolici_VII.djvu)

Not retrieved:
Il Farmaco, Ed. Sci., 13, 893 (1958).

fallen_Angel
(Гиперконструктор)
11-15-03 19:59
No 471091
      Wanted:

2,4,5-trimethoxybenzaldehyde from vanillin
J.Chem.Soc. 1966, ¹23, 2222-2229

Reaction Kondakova (b-alkenyl-b'chloroketone):
Nenitzescu C.D., Balaban A.T., [1],Vol. 3, 1964, Pt. 2, p.1003
Ballaban A.T.., Tetrahedron Letters, 1968,4643

Rhodium
(Chief Bee)
11-16-03 03:11
No 471142
User Picture       References Retrieved by lugh

For Chimimanie:

Comparison of stimulants and hallucinogens on shuttle avoidance in rats
Davis, W. M.; Hatoum, H. T.
General Pharmacology 18(2), 123-8 (1987) (https://www.rhodium.ws/djvu/davis.djvu)

Synthesis and turnover of ³H-5-hydroxytryptamine in the lateral cerebroventricle
Kantak, K. M.; Wayner, M. J.; Tilson, H. A.; Dwoskin, L. P.; Stein, J. M.
Pharmacology, Biochemistry and Behavior 8(2), 153-61 (1978) (https://www.rhodium.ws/djvu/kantak.djvu)

Evaluation of substituted-amphetamine hallucinogens using the cat limb flick model
Rusterholz, D. B.; Spratt, J. L.; Long, J. P.; Barfknecht, C. F.
Communications in Psychopharmacology 1(6), 589-92 (1977) (https://www.rhodium.ws/djvu/rusterholz.djvu)

Further studies on BL-3912A: effects on avoidance behavior of rats with low baselines and on reaction thresholds to electric footshock
Tilson, Hugh A.; Chamberlain, John H.; Gylys, Jonas A.
Pharmacology, Biochemistry and Behavior 6(6), 627-30 (1977) (https://www.rhodium.ws/djvu/tilson.djvu)

Rhodium
(Chief Bee)
11-16-03 23:29
No 471277
User Picture       More refs uploaded

Potential psychotomimetics. New bromoalkoxyamphetamines
Sepulveda, Silvia; Valenzuela, Ricardo; Cassels, Bruce K.
Journal of Medicinal Chemistry 15(4), 413-15 (1972) (https://www.rhodium.ws/pdf/bromoalkoxyamphetamines.pdf)

I have also uploaded the missing file you mentioned.

Chimimanie
(Hive Bee)
11-17-03 04:41
No 471307
User Picture       Wanted Articles

Methoxyamphetamines and fenfluramine compared to amphetamine for antagonism of electroshock seizures
Davis, W. Marvin; Hatoum, Hind T.; Hatoum, Nabil S.
Research Communications in Substances of Abuse (1982), 3(3), 297-305.
____ ___ __ _

Synthesis of Ar-S-R from Ar-Br with Cu²⁺

New synthetic method for 2,5-dimethoxybenzaldehyde.
Chen, Zhi-tao; Xiang, Jian-nan; Li, Zhi-liang.
Chongqing Daxue Xuebao, Ziran Kexueban (2002), 25(2), 109-111.
CODEN: CDXZF2 ISSN: 1000-582X. Journal written in Chinese. CAN 138:73048 AN 2002:335010

_{Abstract
Reimer-Tiemann reaction and a methoxylation through di-Me sulfate are employed for the prepn. of 2,5-dimethoxybenzaldehyde from p-methoxyphenol in this paper. Comparing different phase transfer catalysts, it can be demonstrated that the PEG-10000 is the most favorable catalyst used in Reimer-Tiemann reaction. The yield and quality are improved through the methoxylation of 2-hydroxy-5-methoxy-benzaldehyde in a buffer soln. The diverse factors influencing the yield are examd. Some explanations are given from theor. viewpoint. The proper exptl. conditions are found and the overall yield reached 68%.}
____ ___ __ _

Analysis of the essential oil of Zingiber cassumunar Roxb. from Indonesia.
Taroeno; Brophy, J. J.; Zwaving, J. H. Fac. Pharm., Gadjah Mada Univ., Yogyakarta, Indonesia.
Flavour and Fragrance Journal (1991), 6(2), 161-3.

_{Abstract
The compn. of the Z. cassumunar oil from Indonesia was examd. by gas chromatog. (GC) and GC-mass spectrometry. A major part of the oil consists of monoterpenes with sabinene and terpinen-4-ol as main constituents. Sesquiterpenes accounted for a small part of the oil with sesquiphellandrene being the principal constituent. In addn. to these terpenes the oil contains a no. of phenylbutanoids. The essential oil obtained by steam contained about 25% of these phenylbutanoids whereas, the oil obtained by extn. with light petroleum had about 46% with trans-1-(3,4-dimethoxyphenyl)but-1-ene, trans-1-(3,4-dimethoxyphenyl)butadiene and trans-4-(3,4-dimethoxyphenyl)but-3-ene-1-yl acetate as the main constituents.}

Rhodium
(Chief Bee)
11-17-03 09:21
No 471330
User Picture       2,5-dimethoxy-4-methyl-propenylbenzene

Cross-linking and sequence-specific alkylation of DNA by aziridinylquinones. 3. Effects of alkyl substituents.
Hargreaves, Robert H. J.; O'Hare, C. Caroline; Hartley, John A.; Ross, David; Butler, John.
Journal of Medicinal Chemistry (1999), 42(12), 2245-2250. (https://www.rhodium.ws/pdf/4-me-25-meo-propenylbenzene.pdf)

Isomeric cyclopropyl ring-methylated homologs of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analog.
Jacob, James N.; Nichols, David E.
Journal of Medicinal Chemistry (1982), 25(5), 526-30. (https://www.rhodium.ws/pdf/nichols/nichols-methylated-cyclopropyl-peas.pdf)

Rhodium
(Chief Bee)
11-17-03 12:51
No 471358
User Picture       methamphetamine impurities

GC-MS analysis of methamphetamine impurities: reactivity of (+)- or (-)-chloroephedrine and cis- or trans-1,2-dimethyl-3-phenylaziridine
Lekskulchai V, Carter K, Poklis A, Soine W
J. Anal. Toxicol. 24(7), 602-5 (2000)

S-(+)-Methamphetamine is frequently found as the only isomer in urine specimens from methamphetamine abuseres. Enantiomerically pure S-(+)-methamphetamine can be synthesized from ephedrine or pseudoephedrine via chloroephedrine intermediates. These intermediates are unstable and capable of cyclizing to form cis- and trans-1,2-dimethyl-3-phenyl aziridine. Studies were done to determine if these intermediates could be detected when using a common gas chromatographic-mass spectrometric analytical method (derivatization with heptafluorobutyric anhydride, HFBA) for toxicological screening of methamphetamine. Analysis of (+)- or (-)-chloroephedrine after extraction into hexane and derivatization with HFBA indicated that both pseudoephedrine and ephedrine were the major compounds detected. Direct derivatization of a hexane solution of cis-1,2-dimethyl-3-phenyl aziridine yielded only the derivatives of ephedrine and pseudoephedrine, indicating that the aziridine intermediate is responsible for the formation of the ephedrine or pseudoephedrine. These studies indicate that the aziridine intermediates would not be detected in methamphetamine samples following HFBA derivatization.

azole
(One Remarkable HyperLab Bee)
11-17-03 13:53
No 471364
      Retrieved references

For fallen_Angel:

2,4,5-trimethoxybenzaldehyde from vanillin
J. Chem. Soc. (C), 2222-2229 (1969) (http://hyperlab.0catch.com/J_Chem_Soc_C_2222.djvu)

pyrylium salts by Ac₂O/HClO₄ diacylation of olefins
Tetrahedron Lett., 4643-4644 (1968) (http://hyperlab.0catch.com/TL1968_4643.djvu)

Not retreived:
C.D. Nenitzescu and A.T. Balaban: "Aliphatic Acylation", in "Friedel-Crafts and Related Reactions", editor G.A. Olah, Wiley-Interscience, New York, 1964, vol. 3, pt. 2, pp. 1033-1152

Rhodium
(Chief Bee)
11-17-03 16:42
No 471388
User Picture       Fallen_Angel:

Actually, I apparently do own the "Friedel-Crafts and Related Reactions" 5000-page treatise...

However, scanning 100 pages from that book may be a little too much work with my current setup, could you name any specific sections in the chapter you are looking for?

Table of Contents for Volume III, Part 2, Chapter 37:

fallen_Angel
(Гиперконструктор)
11-19-03 07:56
No 471696
      reaction Kondakova

Conditions realization of reaction Kondakova:
R-COCl + CH2=CH-R1 -> R-COCH2CH(R1)Cl

In particular
CH2=C(R)COCl + CH2=CH2 -> CH2=C(R)COCH2CH2Cl
R=H, CH3, C2H5...

I guess pages 1036-1066, if is it not difficult for you?

Chimimanie
(Hive Bee)
11-19-03 14:11
No 471737
User Picture       2,5-DMA precursors

Identification of new secondary metabolites of methoxyphenamine in man., McKay, G.; Cooper, J. K.; Hawes, E. M.; Roy, S. D.; Midha, K. K.
Xenobiotica (1983), 13(4), 257-64.

Abstract

Metabolites of methoxyphenamine (I) [93-30-1] were examd. in the urine of healthy human volunteers. The metabolites were sepd. by gas liq. chromatog. and identified by comparison of their chromatog. and mass-spectrometric behaviors with those of authentic synthetic compds. 5-Hydroxy-2-methoxy-N-methylamphetamine [61866-76-0], a metabolite previously identified by indirect methods, was conclusively identified by comparison with the now-available authentic synthetic material. In addn., 3 new metabolites of methoxyphenamine were identified 5-hydroxy-2-methoxyamphetamine [87835-15-2], 2-methoxyphenylacetone [5211-62-1] and 5-hydroxy-2-methoxyphenylacetone [87835-16-3].

2,4-Diaminothieno[2,3-d]pyrimidine analogs of trimetrexate and piritrexim as potential inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase. Rosowsky, Andre; Mota, Clara E.; Wright, Joel E.; Freisheim, James H.; Heusner, James J.; McCormack, John J.; Queener, Sherry F.
Journal of Medicinal Chemistry (1993), 36(21), 3103-12.
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1993/36/i21/pdf/jm00073a009.pdf

thanx. smile

Rhodium
(Chief Bee)
11-19-03 18:12
No 471773
User Picture       Very interesting article

2,4-Diaminothieno[2,3-d]pyrimidine analogs of trimetrexate and piritrexim as potential inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase.
Rosowsky, Andre; Mota, Clara E.; Wright, Joel E.; Freisheim, James H.; Heusner, James J.; McCormack, John J.; Queener, Sherry F.
Journal of Medicinal Chemistry 36, 3103-12 (1993) (https://www.rhodium.ws/pdf/methoxy-p2p.wittig.pdf)

Rhodium
(Chief Bee)
11-21-03 19:00
No 472295
User Picture       Requested References for various people

For Chimimanie:
Cross-linking and sequence-specific alkylation of DNA by aziridinylquinones. 3. Effects of alkyl substituents.
Hargreaves, Robert H. J.; O'Hare, C. Caroline; Hartley, John A.; Ross, David; Butler, John.
Journal of Medicinal Chemistry (1999), 42(12), 2245-2250. (https://www.rhodium.ws/pdf/4-me-25-meo-propenylbenzene.pdf)

Isomeric cyclopropyl ring-methylated homologs of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analog.
Jacob, James N.; Nichols, David E.
Journal of Medicinal Chemistry (1982), 25(5), 526-30. (https://www.rhodium.ws/pdf/nichols/nichols-methylated-cyclopropyl-peas.pdf)

The article below is very interesting, as it contains novel routes to phenyl-2-propanones and other fun stuff.

2,4-Diaminothieno[2,3-d]pyrimidine analogs of trimetrexate and piritrexim as potential inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase.
Rosowsky, Andre; Mota, Clara E.; Wright, Joel E.; Freisheim, James H.; Heusner, James J.; McCormack, John J.; Queener, Sherry F.
Journal of Medicinal Chemistry 36, 3103-12 (1993) (https://www.rhodium.ws/pdf/methoxy-p2p.wittig.pdf)
____ ___ __ _

For fallen_angel:

Friedel-Crafts and Related Reactions. Chapter 37, Section I-II: Alkene Acylation
C.D. Nenitzescu & A.T. Balaban
Volume III, Part 2, pp. 1032-1066 (https://www.rhodium.ws/djvu/alkene.acylation.1032-66.djvu)

Friedel-Crafts and Related Reactions. Chapter 37: References
C.D. Nenitzescu & A.T. Balaban
Volume III, Part 2, pp. 1136-1152 (https://www.rhodium.ws/djvu/alkene.acylation.1136-52.djvu)

A Convenient Preparation of Tetrahydro-4H-pyran-2-one
G. R. Owen & C. B. Reese
J. Chem. Soc. C, 2401-2403 (1970) (https://www.rhodium.ws/pdf/beta-dichloroketones.pdf)
____ ___ __ _

For java:

Preparation of Aldehydes from Alkenes by the Addition of Carbon Monoxide and Hydrogen with Cobalt Carbonyls as Intermediates
Homer Adkins, George Krsek
J. Am. Chem. Soc. 70, 383-386 (1948) (https://www.rhodium.ws/pdf/styrene.carbonylation.pdf)

Über die Beziehungen zwischen dem assym. Methyl-phenyl-äthylen-glycol und den ihm entsprechenden Anhydro-Formen
S. Danilow & E. Venus-Danilowa
Chem. Ber. 60, 1050-1069 (1927) (https://www.rhodium.ws/djvu/hydratropaldehyde.djvu)
____ ___ __ _

For lego:

Alkylation of alkyl nitroacetates under PTC conditions
Gogte, V. N.; Natu, A. A.; Pore, V. S.
Synthetic Communications 17(12), 1421-9 (1987) (https://www.rhodium.ws/pdf/nitroacetate.ptc.alkylation.pdf)
Abstract: Treatment of O2NCHRCO2R1 (I; R = H, R1 = Me; R = Me, R1 = Et) with p-R2C6H4CH2Br (R2 = H, Cl, MeO) and KHCO3 in DMF contg. TEBA gave 70-78% p-R2C6H4CH2CR(NO2)CO2R1. Similar treatment of I (R = H, R1 = Me) with p-O2NC6H4CH2Br gave (p-NO2C6H4CH2)2C(NO2)CO2Me.

In situ reagents for thionation of amides, peptides and lactams
Dennis Brillon
Synthetic Communications 20(19), 3085-3095 (1990) (https://www.rhodium.ws/pdf/amide-thionation.pdf)
Abstract: An agent, prepd. from 1:1 P₂S₅ and Na₂CO₃ in situ, is used for thionation of amides, amino acids, peptides, and lactams. Yields range from 28 to 96%.
As mentioned in: Post 468717 (Lego: "Amide to thioamide to amine", Serious Chemistry)

moo
(Hive Bee)
11-22-03 16:05
No 472493
      Here you go Chimimanie: Journal of Medicinal...

For Chimimanie
Synthesis and serotonin receptor affinities of a series of enantiomers of a-methyltryptamines: evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors.
Nichols, David E.; Lloyd, David H.; Johnson, Michael P.; Hoffman, Andrew J.
Journal of Medicinal Chemistry (1988), 31(7), 1406-12. (https://www.rhodium.ws/pdf/nichols/nichols-amt-enantiomers.pdf)

Abstract
(R)- And (S)-a-methyltryptamines I (R = H, 4-OMe, 5-OMe, 6-OMe, 4-OH, 5-OH) were prepd. by treating indoles with CH2:CMeNO2, oxidizing the 3-(2-nitropropyl)indoles to the 2-oxopropyl analogs, reductive amination with (R)- or (S)-PhCHMeNH2, and hydrogenolysis. To probe structure-activity relationships of serotonin receptors, affinities of (R)- and (S)-I were then measured. at the 5-HT2 antagonist receptor subtype, with displacement of [3H]ketanserin, and were estd. at the 5-HT1B receptor, with displacement of [3H]serotonin, in rat frontal cortex homogenates. Enantioselectivity at the receptor subtypes varied, depending on R. (S)-I (R = 5-OH, 5-OMe) had higher affinity or was equipotent to the R enantiomer. This selectivity at [3H]serotonin binding sites was reversed for I (R = 4-OH, 4-OMe) R did not enhance affinity over I (R = H). These results can be explained, for the [3H]serotonin displacement data, if the binding conformation is one where the ethylamine side chain is trans and lysing in a plane perpendicular to the indole ring plane.

_{fear fear hate hate}

Lego
(Hive Bee)
11-22-03 17:51
No 472506
User Picture       Thanks, but Lego has another Synth. Comm. article

Edit: article retrieved and posted in Post 473295 (azole: "ArNH2 --> ArSMe via aryldiazonium + CuSMe", Novel Discourse)

The facile conversion of aromatic amines to aryl methyl sulfides with methylthiocopper.
Baleja, James D. Dep. Chem., Univ. Manitoba, Winnipeg, MB, Can.
Synthetic Communications (1984), 14(3), 215-18.

Abstract
Benzenediazonium salts were treated with CuSMe to yield RSMe (R = Ph, NCC6H4, MeSC6H4, alkoxyphenyl, di- or trihalophenyl, naphthyl). Thus, 4-MeSC6H4NH2 was diazotized in water contg. H2SO4, and the mixt. was added to CuSMe to give 1,4-(MeS)2C6H4.

The candle that burns twice as bright burns half as long

azole
(One Remarkable HyperLab Bee)
11-26-03 18:10
No 473326
      for Lego

For Lego:

Alkene Reductions Employing Ethyl Acetate - Hydroxylamine, a Useful New Source of Diimide
P. A. Wade, N. V. Amin
Synthetic Communications, 12(4), 287-91 (1982). (http://hyperlab.0catch.com/SynthCommun1982_12_287_1.djvu)

Abstract
The reaction of alkenes with HN=NH (formed in situ from EtOAc and excess NH₂OH) gave the resp. alkanes. Thus, KOH was added to 0.50 mol NH₂OH.HCl, 0.22 mol EtOAc was introduced, and 0.010 mol 2-decen-1-ol was treated with the mixt. to give 1-decanol. Similarly, PhCH=CHCH₂OH was converted to Ph(CH₂)₃OH.

Chimimanie
(Hive Bee)
11-28-03 20:44
No 473673
User Picture       Russian tryptophol synthesis refs

Hi! Can any of you (russian bee or not) fetch this paper and that patent from Grandberg about tryptophol synthesis by reaction between dihydrofuran and phenylhydrazine?

Indoles. XXXII. Synthesis of tryptophols.
Grandberg, I. I.; Moskvina, T. P. Mosk. S.-Kh. Akad. im. Timiryazeva, Moscow, USSR.
Khimiya Geterotsiklicheskikh Soedinenii (1972),   (10), 1366-7.
Journal written in Russian.

Abstract

Tryptophols I (R = R1 = H; R = 5-Me, R1 = H; R = 7-Me, R1 = H; R = 7-MeO, R1 = H; R = H, R1 = Me; R = H, R1 = PhCH2) were prepd. in 20-70% yields by condensing RC6H4NR1NH2.HCl with dihydrofuran.

Tryptophol or homotryptophol.
Grandberg, I. I.; Afonina, N. I. (Timiryazev, K. A., Agricultural Academy).
U.S.S.R. (1969),    CODEN: URXXAF russian patent SU 239341 19690318
Patent written in Russian. Application: SU 19671104.

Abstract

The title compds. are prepd. by treating an arylhydrazine salt with dihydrofuran or dihydropyran (at an elevated temp.) in an aprotic solvent.

thanx! smile

Lego
(Hive Bee)
11-29-03 17:40
No 473786
User Picture       The Sandmeyer Reaction

A novel metal promoter for the Sandmeyer reaction.
Anon. UK. CODEN: RSDSBB ISSN: 0374-4353. CAN 103:87565 AN 1985:487565
Research Disclosure (1985), 252 171.

Abstract
Fe²⁺ halide or Fe^o-Fe³⁺ system as a promoter for the Sandmeyer reaction, wherein Cu⁺ causes detrimental side effects in the case of Me-substituted or ortho-substituted arenediazonium salts, was discussed. The oxidn. of pendant Me groups was not evident in the Fe system and the reaction was applicable to a wide variety of functional groups. The Fe system is less expensive than Cu⁺ and more friendly environmentally.

The candle that burns twice as bright burns half as long

azole
(One Remarkable HyperLab Bee)
12-01-03 19:05
No 474111
      retrieved references

For Lego:

An improved preparation of phenylacetone.
J. Kizlink
Chemicke Listy (1990), 84(9), 993-4. (http://hyperlab.0catch.com/ChemickeListy_1990_84_993.djvu)

Oxidation of nitromethane by manganese(III) acetate: novel formation of methyl radical.
Srivastava, Ranjan P.; Seth, M.; Bhaduri, A. P.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1989), 28B(1), 65-6. (http://hyperlab.0catch.com/IndJChem_1989_28B_65.djvu)

Synthesis of nitroalkanes from bromoalkanes by phase-transfer catalysis.
Sane, Pramodchandra V.; Sharma, Man Mohan
Organic Preparations and Procedures International (1988), 20(6), 598-9.
(http://hyperlab.0catch.com/OPPI_1988_20_598.djvu)

Preparation of N-unsubstituted thioamides by a modified Willgerodt-Kindler reaction.
You, Qidong; Zhou, Houyuan; Wang, Qizhou; Lei, Xinghan
Organic Preparations and Procedures International (1991), 23(4), 435-8. (http://hyperlab.0catch.com/OPPI_1991_23_435.djvu)

Improved synthesis of phenylacetamides by the Willgerodt reaction with microwave heating.
Strauss, Christopher R.; Trainor, Robert W.
Organic Preparations and Procedures International (1995), 27(5), 552-5. (http://hyperlab.0catch.com/OPPI_1995_27_552.djvu)

Selective reduction of nitro compounds with titanium(II) reagents.
J. George and S. Chandrasekaran
Synthetic Communications, 13(6), 495-9 (1983). (http://hyperlab.0catch.com/SynthCommun_1983_13_495.djvu)

The following articles are in Russian:

Methylation of phenol with methyl formate.
Nasadyuk, V. A.; Fedevich, E. V.; Pazderskii, Yu. A.; Moiseev, I. I.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, 787-90. (http://hyperlab.0catch.com/IzvAN_1989_787.djvu)

Reactions of hydrazine derivatives. XVII. New synthesis of α-methyltryptophol.
Grandberg, I. I.; Kost, A. N.; Terent'ev, A. P.
Zhurnal Obshchei Khimii, 27, 3342-5 (1957) (http://hyperlab.0catch.com/ZhOKh_1957_3342.djvu)

Abstract
Heating 10.8 g. PhNHNH2, 10.2 g. AcCH2CH2CH2OH, and 6 ml. AcOH 0.5 hr. at 100° gave after addn. of NH4OH and extn. with Et2O 88.5% PhNHN:CMeCH2CH2CH2OH (I), b8 194-6°, m. 60-6°. Reaction of 51 g. AcCH2CH2CH2Cl and 48.6 g. PhNHNH2 in EtOH gave after 1 hr. on steam bath 52.4% 1-phenyl-3-methyl-1,4,5,6-tetrahydropyridazine, b6 197-8° (picrate, m. 226.5°). Heating 15.7 g. PhNHNH2 and 15.3 g. AcCH2CH2CH2OH 1 hr. on steam bath, heating in vacuo to 150° to remove H2O, addn. of 0.2 g. Cu2Cl2 and heating to 230° 2 hrs. gave 69.4% a-methyltryptophol (II), b7-8 202-4°, m. 52-5° (picrate, m. 132°); use of ZnCl2 as catalyst gave 63% yield. I and AcCl in dioxane-CCl4 gave 33.4% O-acetyl-a-methyltryptophol, b3-4 196-204° (picrate, m. 131.5°), also formed from II and Ac2O at reflux. II and PBr3 in Et2O gave after an aq. treatment 70.3% a-methyl-b-(b-bromoethyl)indole, m. 58°, which with aq. Me2NH at 100° gave 66.5% a-methyl-b-(b-dimethylaminoethyl)indole, b21 204-5°, m. 93-5° (picrate, m. 176°). Cf. Hoshinyo, et al. C.A. 29, 79757.

For Chimimanie:

Indoles. XXXII. Synthesis of tryptophols.
Grandberg, I. I.; Moskvina, T. P.
Khimiya Geterotsiklicheskikh Soedinenii, 1972(10), 1366-7 (http://hyperlab.0catch.com/KhGS_1972_1366.djvu)

The last article is reviewed in the book "Preparative Chemistry of Indole" (in Russian) along with several other articles concerning tryptophols by the same author (I.I.Grandberg).

Rhodium
(Chief Bee)
12-02-03 18:51
No 474329
User Picture       arylations for java

For Java:
Palladium-catalyzed arylation of siloxycyclopropanes with aryl triflates. Carbon chain elongation via catalytic carbon-carbon bond cleavage
Satoshi Aoki, Tsutomu Fujimura, Eiichi Nakamura, Isao Kuwajima
J. Am. Chem. Soc. 110, 3296-3298 (1988) (https://www.rhodium.ws/pdf/arylation.pd-triflate.pdf)

Ferrous ion catalysis of reactions of nucleophiles with aryl halides
Carlo Galli, J. F. Bunnett
J. Org. Chem. 49, 3041-3042 (1984) (https://www.rhodium.ws/pdf/arylation.ferrous-srn1.pdf)

Summary
Reactions of ketone enolate ions and of diethyl phosphite ion with bromo- and iodobenzene in ammonia or dimethyl sulfoxide solution occur in preparatively useful amounts under catalysis by iron(II)salts, apparently via the SRN1 mechanism.

Rhodium
(Chief Bee)
12-03-03 20:04
No 474524
User Picture       Electrosynthesis of Nitroalkenes

Synthesis of some fluorinated nitro-olefins
R. Jacobo, A. Cota, E. Rogel, J. D. Garcia, I. A. Rivero, L. H. Hellberg and R. Somanathan
Journal of Fluorine Chemistry, 67(3), 253-255 (1994)
DOI:10.1016/0022-1139(93)02969-L
____ ___ __ _

Synthesis of (R)- and (S)-amphetamine-d3 from the corresponding phenylalanines
Gal J.
J Labelled Comp Radiopharm 13, 3-9 (1977)
____ ___ __ _

A Study of the Precursors, Intermediates and Reaction By-Products on the Synthesis of MDMA and its Application to Forensic Drug Analysis.
Renton, R.J., Cowie, J.S. and Oon, M.C.
Forensic Science International 60, 189-202 (1993)
Summary: MDMA was prepared by three separate synthetic routes, and the trace byproducts and impurities were identified and presented in a way that probable synthetic method could be deduced for legal purposes.
____ ___ __ _

How Similar is substantially Similar?
Alexander Shulgin
Journal of Forensic Sciences 35, 8 (1990)

azole
(One Remarkable HyperLab Bee)
12-05-03 14:27
No 474815
      retrieved...

For Rhodium:

<Preparation of 4-halobutanal acetals.>, from
M. G. Pleshakov, A. E. Vasil'yev, I. K. Sarycheva, and N. A. Preobrazhenskii
Zhurnal Obshchei Khimii, 31(5), 1545-7 (1961).
C. A., 55, 23339 (1961)
Probably, J. Gen. Chem. USSR, 31, 1433 (1961) is the same article translated into English. I can only guess since I have no access to the English version of the journal.
2-(γ-Chloropropyl)-1,3-dioxolane. A stream of hydrogen was passed into a refluxing mixture of γ-chlorobutyric acid chloroanhydride (35 g) [5], toluene (200 ml), and Pd/BaSO₄ (3.5 g) [6] until hydrogen chloride evolution ceased [7]. The catalyst was separated and conc. H₂SO₄ (0.5 ml) and ethylene glycol (40 ml) were added to the filtrate with stirring at 18-20°. The resulting mixture was refluxed for 4 h [8]. After removal of the solvent, the residue was distilled. Yield 23.9 g (64.2%), b.p. 78-79° (10 mm Hg), d²⁰₄ 1.1520, n²⁰_D 1.4548 .

2-(γ-Iodopropyl)-1,3-dioxolane. A mixture of 2-(γ-chloropropyl)-1,3-dioxolane (30 g), acetone (200 ml) and sodium iodide (45 g) was refluxed for 12 h. Then the reaction mixture was cooled to 18-20° and the precipitate was separated. After removal of the solvent, the residue was distilled. Yield 29.9 g (62.1%), b.p. 69-70° (0.6 mm Hg), d²⁰₄ 1.6971, n²⁰_D 1.5248 .

   5. W. J. Close, J. Amer. Chem. Soc., 79, 1455 (1957).
   6. E. Mosettig, R. Mozingo, in: Org. React., vol. IV, p. 368. Originally, the authors refer to the Russian translation of this series, the page number was given for the experimental part.
   7. Patent GB700825.
   8. S. S. Nigam, B. C. L. Weedon, J. Chem. Soc., 1956, 4049.

[Edit]

A Convenient Preparation of Conjugated Nitro Olefins by Electrochemical Method.
A. Kunai, Y. Yanagi, and K. Sasaki
Tetrahedron Lett., 24(41), 4443-4444 (1983). (http://hyperlab.0catch.com/TL_1983_v24_No41_4443.djvu)

For pHarmacist:

A One-step Ester to Hydrocarbon Reduction.
Donald C. Wigfield and Kevser Taymaz
Tetrahedron Lett., 49, 4481-4484 (1973). (http://hyperlab.0catch.com/TL_1973_49_4841.djvu)

[/Edit]

pHarmacist
(pHantasticant)
12-05-03 14:35
No 474816
User Picture       Lili's post

Maybee someone can get the ref that Lili was talking about in: Post 474534 (Lilienthal: "While looking through old cannabinoid papers I", Novel Discourse) i myself can't get tet. lett from prior to 1995

(¯`·.¸(¯`·.¸ http://www.bassdrive.com/BassDrive.m3u ¸¸.·´¯)¸.·´¯)

lugh
(Moderator)
12-05-03 22:00
No 474877
      Retrieved References

That article was retrieved, scanned and uploaded to Post 474847 (lugh: "Request Retrieved", Novel Discourse), the file extension has to be renamed to djvu presently crazy

For Rhodium:

J. Anal. Toxicol. 24(7), 602-5 (2000)

Tetrahedron Letters 24(41), 4443-4444 (1983)

For Lego:

Plant Physiol. 42: 520-524

For Chimimanie:

Arzneimittel-Forschung (2001), 51(7), 535-544

Phytochemistry (Elsevier) (1981), 20(5), 1164-5

Chemical & Pharmaceutical Bulletin (1980), 28(10), 2948-59

For pHarmacist:

Chem. Pharm. Bull., 1985, 33, 3696

Chemistry is our Covalent Bond

java
(Hive Bee)
12-06-03 22:37
No 475078
      Ketone by the 2-Phenylpropanal and dil H2SO4

S. N. Danilov, Zhur. Obschei. Khim (J Gen Chem) 18, 2000-2007 (1948)

Although metioned by ...

Post 424552 (Dionket: "J Org Chem USSR ?", Russian HyperLab)

and an attempted and appreciated, translation by Timmy...

Post 446720 (Timmy: "So it is...", Russian HyperLab)

I would like to have the translation of the article in english , as the topic of refluxin the 2-phenylpropanal in H2SO4 seems interesting , but more so I want to find out if there is any unreduced 2-phenylpropanal and if so, then it must then be oxidised and salted out with a KOH solution to free up the pure P2P........so I think!.....java

We're all in this world together,
http://www.aztlan.net

Terminator
(Newbee)
12-11-03 02:45
No 476041
      Here's the article mentioned here Post 316637...

Here's the article mentioned here
Post 316637 (3base: "safrole > isosafrole (solventless/microwave)", Novel Discourse)

http://home.ripway.com/2003-12/43034/Chemtext1/TapChi37-1-92-94p.pdf

I have the Tap Chi article here
Post 217986 (Rhodium: "Wanted references", Novel Discourse)
but I haven't scanned it yet. It basically involves isomerization in a closed container at high temperature.

azole
(One Remarkable HyperLab Bee)
12-12-03 18:55
No 476443
      as requested by java

[I would like to have the translation of the article in english , as the topic of refluxin the 2-phenylpropanal in H2SO4 seems interesting , but more so I want to find out if there is any unreduced 2-phenylpropanal and if so, then it must then be oxidised and salted out with a KOH solution to free up the pure P2P........so I think!.....java

Post 476441 (azole: "as requested by java", Russian HyperLab) - see the article translated.

Chimimanie
(Hive Bee)
12-13-03 03:38
No 476545
User Picture       eugenol -> asarone spanish ref

New synthetic route for the preparation of potentially hypocholesterolemic analogs of a-asarone. Determination of E/Z isomer content in natural and synthetic mixtures of a-asarone and its analogs.
Munoz, Heber; Diaz, Francisco; Sanchez, Adrian; Barajas, Marcelino; Labarrios, Fernando; Tamariz, Joaquin. Escuela Nac. Cienc. Biol., Inst. Politec. Nac., Mexico City, Mex.
Acta Mexicana de Ciencia y Tecnologia (1993), 11(41), 51-62.
Journal written in Spanish.

Abstract

A new and improved synthesis of potentially hypocholesterolemic (no data) (E)-2,4,5-R(MeO)2C6H2CH:CHMe [I, R = NO2, NH2] from eugenol is described. This pathway also allows the prepn. of the 2-propenyl analogs. Moreover, 5,6-dimethoxy-2-methylindole was also prepd. efficiently by this method. b-Asarone and (Z)-I [R = NO2] were also prepd. and the isomer ratios in natural and synthetic samples of a-asarone and I [R = NO2] detd. by GC/MS.

java
(Hive Bee)
12-13-03 04:34
No 476557
      Re:Acta Mexicana de Ciencia y Tecnologia

It's here...............needs translation......java

Acta Mexicana de Ciencia y Tecnologia, 11(41), 51-62 (1993) (https://www.rhodium.ws/pdf/asarone.nueva.ruta.pdf) ;

We're all in this world together,
http://www.aztlan.net

jsorex
(Hive Bee)
12-15-03 00:59
No 476869
User Picture       Re: Indian J. Chem., Sect B 33, 2, 182-83...

Indian J. Chem., Sect B 33, 2, 182-83 (1994)

Found it at a library, somebody had nicked it though!

-jsx

jsorex
(Hive Bee)
12-15-03 01:17
No 476871
User Picture       Re: It's here...............needs ...

It's here...............needs translation......java

Acta Mexicana de Ciencia y Tecnologia, 11(41), 51-62 (1993) (https://www.rhodium.ws/pdf/asarone.nueva.ruta.pdf) ;

But it's so fucking long!

-jsx

Rhodium
(Chief Bee)
12-15-03 02:14
No 476879
User Picture       how odd comments you post

Found it at a library, somebody had nicked it though!

And what use do we have of that info?

But it's so fucking long!

Yes, but one can always restrict the translation to the experimental part.

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
12-17-03 15:43
No 477411
User Picture       For Vitus_Verdegast

Here you go, please transcribe the sections of interest and post in a suitable thread...

A Synthesis of N-(3-Methoxybenzyl)-N-methyl-3-methoxy-4,5-methylenedioxyphenethylamine
K. E. Hamlin, Arthur W. Weston
J. Am. Chem. Soc. 71, 2210-2212 (1949) (https://www.rhodium.ws/pdf/3-meo-45-mdpea.pdf)

...and here is the Milas V₂O₅ oxidation protocol referenced in the above document.

The Hydroxylation of Unsaturated Substances. III. The Use of Vanadium Pentoxide and Chromium Trioxide as Catalysts of Hydroxylation
Nicholas A. Milas
J. Am. Chem. Soc. 59, 2342-2344 (1937) (https://www.rhodium.ws/pdf/v2o5.propenylbenzene2benzaldehyde.pdf)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
12-17-03 21:33
No 477464
User Picture       Retrieved references

For Merbst:
Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 8. 14-Methoxymetopon, an Extremely Potent Opioid Agonist
H. Schmidhammer, A. Schratz, J. Mitterdorfer
Helv. Chim. Acta. 73, 1784-87 (1990) (https://www.rhodium.ws/pdf/14-methoxymetopon.pdf)

For Relux:
GABA to GBL using NaNO₂
Bull. Soc. Chim. Fr. (1) 88-94 (1989)
Posted in Post 477462 (Rhodium: "Hydrolytic Nitrosation of Amino Acids with NaNO2", Chemistry Discourse)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
12-17-03 21:50
No 477469
User Picture       Article beyond my grasp

5-Hydroxyvanillin to Myristicinaldehyde in 77% Yield
Taniguchi, Eiji; Imamura, Keiichi; Ishabashi, Fumito; Matsui, Toshio; Nishio, Akira
Agric. Biol. Chem.; 53(3) 631-644 (1989)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
12-19-03 03:33
No 477752
User Picture       Methoxylation of aryl bromides

The copper catalysed reaction of sodium methoxide with aryl bromides, a mechanistic study leading to a facile synthesis of anisol derivates
Aalten et al.
Tetrahedron 45, 5565-5578 (1989)

^{The Hive - Clandestine Chemists Without Borders}

merbst
(Stranger)
12-22-03 10:07
No 478387
      Wanted Reference

If anyone has the time, I most humbly beg to see the contents of this article:

Optimization of the Synthesis of Oxycodone and 5-Methyloxycodone
R. KRASSNIG, C. HEDERER, H. SCHMIDHAMMER
Arch. Pharm. Med. Chem. 1996, 329, 325 (1996)

The Journal itself http://www3.interscience.wiley.com/cgi-bin/jtoc/5007844/all has archives back to 1998, unfortunately this article is from 1996.

5-Methyloxymorphone is also known as Metopon, an analgesic with few side effects, and a low physical dependance capacity.

Herr_Ovalmeister
(Hive Bee)
12-24-03 03:27
No 478764
      Here's Russian patent SU 239341 in TIFF ...

Here's Russian patent SU 239341 in TIFF format.

http://home.ripway.com/2003-12/43034/patents/SU239341a.tif

http://home.ripway.com/2003-12/43034/patents/SU239341b.tif

N'être que de la drogue

Rhodium
(Chief Bee)
12-28-03 15:29
No 479475
User Picture       Routes from Alcohols to Amines

In Situ Oxidation-Imine Formation-Reduction Routes from Alcohols to Amines
Leonie Blackburn and Richard J. K. Taylor
Org. Lett. 3(11) 1637-1639 (2001) (https://www.rhodium.ws/pdf/alcohol2amine.pscbh.pdf)
DOI:10.1021/ol015819b

Abstract
Manganese dioxide is employed as an in situ oxidant for the one-pot conversion of alcohols into imines. In combination with polymersupported cyanoborohydride (PSCBH), a one-pot oxidation-imine formation-reduction sequence is reported. This procedure enables alcohols to be converted directly into both secondary and tertiary amines.

^{The Hive - Clandestine Chemists Without Borders}

7is
(Stranger)
01-04-04 00:45
No 480322
      Articles retrieved

Drug Discrimination and Receptor Binding Studies of N-Isopropyl Lysergamide Derivates
Huang, Marona-Lewicka, Pfaff, Nichols
Pharmacology, Biochmistry and Behavior 47(3), 667-673 (1994) (https://www.rhodium.ws/pdf/nichols/nichols-n-isopropyl-lysergamide.pdf)

Ergot Peptide Alkaloid Spectra of Claviceps-Infected Tall Fescue, Wheat, and Barley
James K. Porter, Charles W. Bacon, Ronald D. Plattner, and Richard F. Arrendale.
J. Agric. Food Chem. 35, 359-361 (1987) (https://www.rhodium.ws/pdf/ergot.peptide.alkaloid.spectra.pdf)

Synthesis of some fluorinated nitro-olefins
R. Jacobo, A. Cota, E. Rogel, J. D. Garcia, I. A. Rivero, L. H. Hellberg and R. Somanathan
Journal of Fluorine Chemistry, 67(3), 253-255 (1994) (http://nic-nac-project.de/~tajkor/17.pdf)
DOI:10.1016/0022-1139(93)02969-L

I have access to most of the journals published by Elsevier, they now have pdf-articles back to year 1939:
http://www.sciencedirect.com/

lugh
(Moderator)
01-06-04 00:31
No 480620
      Requested Amphetamine Synthesis

For Rhodium:
Synthesis of (R)- and (S)-amphetamine-d3 from the corresponding phenylalanines
Gal J.
J. Labelled Comp. Radiopharm. 13, 3-9 (1977)

smile

Chemistry is our Covalent Bond

dioulasso
(Stranger)
01-06-04 02:50
No 480658
      Retrieved:

A few articles requested some time ago:

For Rhodium:

Copper(II)-B -cyclodextrin aided oxidation of eugenol
Indian Journal Of Chemistry. Sect. B. 42(2), 369-371 (2003)

http://www.angelfire.com/scary/beedioulasso/e1.djvu
http://www.angelfire.com/scary/beedioulasso/e2.djvu
http://www.angelfire.com/scary/beedioulasso/e3.djvu

Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds
Indian Journal Of Chemistry. Sect. B. 42(1), 180-183 (2003)

http://www.angelfire.com/scary/beedioulasso/zn1.djvu
http://www.angelfire.com/scary/beedioulasso/zn2.djvu
http://www.angelfire.com/scary/beedioulasso/zn3.djvu
http://www.angelfire.com/scary/beedioulasso/zn4.djvu

Reduction of oximes with NaBH4/CuSO4/MeOH
Indian journal of chemistry. Section B, 41(5):1072-1074 (2002)

http://www.angelfire.com/scary/beedioulasso/or1.djvu
http://www.angelfire.com/scary/beedioulasso/or2.djvu
http://www.angelfire.com/scary/beedioulasso/or3.djvu

NaBH4/I2 reductive amination
Indian Journal of Chemistry Sect. B, 41(9), 1970-1971 (2002)

http://www.angelfire.com/scary/beedioulasso/ra1.djvu
http://www.angelfire.com/scary/beedioulasso/ra2.djvu

(claimed to work only for benzaldehydes, not aliphatic carbonyl compounds) frown

For Vitus Verdegast:

Solvent-free Microwave Knoevenagel condensation catalyzed by NaCl or NH4OAc-AcOH
Indian Journal of Chemistry, Sect. B. 2000, 39(6) 403-405

http://www.angelfire.com/scary/beedioulasso/k1.djvu
http://www.angelfire.com/scary/beedioulasso/k2.djvu
http://www.angelfire.com/scary/beedioulasso/k3.djvu

(GOOD STUFF!) cool

" Unorthodox cooking, illicit cooking. A bit of real science, in fact. "

Rhodium
(Chief Bee)
01-06-04 21:39
No 480797
User Picture       Digital gifts for roger & pH...

For roger2003
Zur Kenntnis der Glyoxylsäure
Hans Meyer
Chem. Ber. 34, 3593-93 (1904) (https://www.rhodium.ws/pdf/glyoxylic.ber.37.3592.1904.pdf)

For pHarmacist
Deveral Derivatives of p-Chlorophenoxyacetic Acid
N. A. Zakharova, et al.
Chemical Abstracts, Vol 63, 17948 (1965) (https://www.rhodium.ws/pdf/p-chlorophenoxyacetic.pdf)
(Unfortunately I believe that you will have to make do with only the abstract - Rumor says that odd journal is only kept in a total of five libraries in the western world...)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
01-08-04 02:01
No 481030
User Picture       repost of dioulasso's findings

These are the articles retrieved by dioulasso in Post 480658 (dioulasso: "Retrieved:", Novel Discourse) (I simply bundled the separate djvu pages and uploaded the files to my page)

For Rhodium:

Copper(II)-B-cyclodextrin aided oxidation of eugenol
Indian Journal Of Chemistry. Sect. B. 42(2), 369-371 (2003) (https://www.rhodium.ws/djvu/cu-cyclodextrin.eugenol.ox.djvu)

Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds
Indian Journal Of Chemistry. Sect. B. 42(1), 180-183 (2003) (https://www.rhodium.ws/djvu/nitro2amine.zn-n2h4.djvu)

Reduction of oximes with NaBH4/CuSO4/MeOH
Indian journal of chemistry. Section B, 41(5):1072-1074 (2002) (https://www.rhodium.ws/djvu/oxime-reduction.nabh4-cuso4.djvu)

NaBH4/I2 reductive amination
Indian Journal of Chemistry Sect. B, 41(9), 1970-1971 (2002) (https://www.rhodium.ws/djvu/redamin.nabh4-i2.djvu)
(claimed to work only for benzaldehydes, not aliphatic carbonyl compounds)

For Vitus Verdegast:

Solvent-free Microwave Knoevenagel condensation catalyzed by NaCl or NH4OAc-AcOH
Indian Journal of Chemistry, Sect. B. 39(6), 403-405 (2000) (https://www.rhodium.ws/djvu/knoevenagel.zncl2.djvu)

Cobalt(II)Chloride Hexahydrate - Zinc - DMF - Water: An Efficient System for the Reduction of Aldehydes to Alcohols
Indian Journal of Chemistry, Sect. B. 33, 182-183 (1994) (https://www.rhodium.ws/djvu/aldehyde2alcohol.cocl2-zn-dmf-h2o.djvu)

^{The Hive - Clandestine Chemists Without Borders}

Manichi
(Stranger)
01-08-04 22:27
No 481243
User Picture       useful for 2C-Ts + pharmaco triO stuff

This reference describe the preparation of 2-Hydroxy-5-methoxythiophenol. This is a very useful precursor.

Synthesis of Aminomethyl Derivatives of 2-Hydroxy-5-methoxythiophenol

Abstract
Reacting p-methoxyphenol with sulfur monochloride we obtained 2-hydroxy-5-methoxythio-phenol.The latter yields by Mannich reaction with formaldehyde and secondary amines aminomethyl derivatives of 2-hydroxy-5-methoxythiophenol.

Russ.J.Org.Chem. 32, 10, 1996, 1502-1504; in english, or in russian: Zh.Org.Khim., 32, 10, 1996, 1552-1554.

also those two refs from JMC please:

Shulgin, JMC, 1968, p186
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1968/11/i01/pdf/jm00307a056.pdf

and

Glennon, JMC, 1992, p734
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1992/35/i04/pdf/jm00082a014.pdf

also this one, linked in Post 453382 (Rhodium: "Related SAR article, with DOF/DOI/DON synth", Serious Chemistry) but the file is not found:

Glennon, JMC, 1982, p1163
http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1982/25/i10/pdf/jm00352a013.pdf

7is
(Stranger)
01-09-04 04:03
No 481341
      For Manichi

Binding of Phenylalkylamine Derivatives at 5-HT1C and 5-HT2 Serotonin Receptors: Evidence for a Lack of Selectivity
Richard. A. Glennon
J. Med. Chem, 734 (1992) (http://nic-nac-project.de/~tajkor/jm00082a014.pdf)

The Ethyl Homologs of 2,4,5-Trimethoxyphenylisopropylamines
Alexander T. Shulgin
J. Med. CHem 11, 196-187 (1968) (http://nic-nac-project.de/~tajkor/jm00307a056.pdf)

http://nic-nac-project.de/~tajkor/jm00352a013.pdf

Edit: This latter article is accessible in Post 453382 (Rhodium: "Related SAR article, with DOF/DOI/DON synth", Serious Chemistry) at the moment, it might have been a temporary glitch /Rhodium

azole
(One Remarkable HyperLab Bee)
01-09-04 19:22
No 481441
      For Manichi: Zh. Org. Khim.

For Manichi:

Synthesis of Aminomethyl Derivatives of 2-Hydroxy-5-methoxythiophenol
Zh. Org. Khim., 32, 1552-1554 (1996) (http://hyperlab.0catch.com/ZhOrgKh_1996_32_1552.djvu) (journal written in Russian).

Abstract
Reacting p-methoxyphenol with sulfur monochloride we obtained 2-hydroxy-5-methoxythio-phenol.The latter yields by Mannich reaction with formaldehyde and secondary amines aminomethyl derivatives of 2-hydroxy-5-methoxythiophenol.

An excerpt from the experimental part:

2-Hydroxy-5-methoxythiophenol (II). To a solution of purified 4-methoxyphenol (I) (30 g) in benzene (100 ml) was added freshly distilled sulfur monochloride (16.2 g) over the course of 45 min at 40-45 °C. The reaction mixture was heated in a water bath until evolution of HCl ceased. Zinc dust (100 g) was added at 5-10 °C to the product obtained, followed by slow dropwise addition of conc. hydrochloric acid (500 ml). Then the reaction mixture was stirred for 1 h and heated in a water bath for 5 h. The mixture was extracted with benzene and washed with water. After evaporation of benzene, the residue was distilled under reduced pressure. Yield 40%, m. p. 29-30 °C.

More detailed translation will come soon.

7is
(Stranger)
01-12-04 09:00
No 481979
      For Potter

http://nic-nac-project.de/~tajkor/18.pdf
Colour reactions of some aromatic ethers found in essential oils
Janet E. Forrest, R. Richard and R. A. Heacock
Journal of Chromatography A
Volume 65, Issue 2 , 23 February 1972, Pages 439-444

Vitus_Verdegast
(Hive Addict)
01-25-04 14:46
No 484514
User Picture       a-ethynylamphetamine & phenoxyethylamines

As posted in Post 475500 (Nicodem: "Modifications on the side chain (again)", Novel Discourse) :

“The alpha-methyl group of amphetamine itself can be replaced by allyl, ethyl, or ethynyl groups of electron-donating character, without deleterious effects on centrally-mediated actions [1,2], but replacement by electron-withdrawing groups, such as cyano [3] or trifluoromethyl [4], abolishes amphetamine-like properties.”

[1] Burger, Zimmermann, Ariens (1966), J. Med. Chem. , 9, 469. [Retrieved]
[2] Shamano, Hitchens, Goldstein, Beiler (1968), Arch. int. Pharmacodyn. Ther. , 172, 251.
[3] Pinder, Burger, Ariens (1970), Arzeim.-Forsch. , 20, 245. [Retrieved]
[4] Pinder, Burger (1967), J. Pharm. Sci., 56, 970. [Retrieved]

If anybody can find and post them, these are the refs for the phenoxyethylamines:
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 4 (1969), 334.
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 5 (1970), 337.
(European J. of Med. Chem. stil had the title Chim. Ther. in those times)
Rougeul, A.; Laval. med., 40 (1969), 37.
Rougeul, A. and Verdaux, J.; Rev. Can. Biol., 31 (1972), 49.

I like to watch (http://www.churchofeuthanasia.org/iltow_100k.wmv)

silenziox
(Hive Bee)
01-26-04 05:22
No 484609
User Picture       Does anyone have Ninth National Convention,...

Does anyone have Ninth National Convention, Royal Australian Chemical Institute, Monash University, 6-11 December, 1992. "Aluminium Hydride/Amide Chemistry", with Jerry L. Atwood, Stacey M. Lawrence, Fu Chin Lee, Colin L. Raston and Kerry D. Robinson. ? Would be appreciated!

Holotna Pravda... Neskolko dnej iz zhizni siLENZiova   laugh

7is
(Stranger)
01-26-04 18:03
No 484675
      For Vitus

1-Ethynylphenethylamine
Alfred Burger, Stuart E. Zimmerman, and E. J. Ariëns
(1966), J. Med. Chem. , 9, 469.
http://nic-nac-project.de/~tajkor/19.pdf

Rhodium
(Chief Bee)
01-27-04 00:37
No 484738
User Picture       1,2-Dimethyl-3-phenylaziridine

The formation and chemical properties of diastereomeric 1,2-Dimethyl-3-phenylaziridine
T. Taguchi & M. Kojima
Chem. Pharm. Bull. 7, 103-107 (1959)

^{The Hive - Clandestine Chemists Without Borders}

murmur
(HyperLab Bee)
01-28-04 09:06
No 485061
      1-(Dimethylamino)-2-bromopropane HBr

1-(Dimethylamino)-2-bromopropane HBr
Surnin, V. A.; Zenkevich, I. G.; Lobanov, P. S.; Potekhin, A. A.
Zh.Org.Khim. 19(11), 2288-2294 (1983)

Only exp. part:
1-(Dimethylamino)-2-propanol HBr(0.22 mol)and Pbr₃ (0.08 mol) was heated under refluxing condenser on open flame until reaction begins (melting of salt and vigorous boiling up of react. mixt.), then heat was withdrawn and flask shaked up until boiling ends.
Thus obtained oil crystallized on cooling. An exsess of PBr₃ was disst. in vacuo, crystalline residue was precipitated by Et₂O from abs. EtOH and recryst. from EtOH.
Yield 86%, mp=179-181°C.
Authors give the following reference: M.Lefler, R.Adams. J.Am.Chem.Soc. 59, 2252 (1937)

Lego
(Hive Bee)
01-29-04 01:04
No 485184
User Picture       For Vitus - modifications of the side chain

J. Pharm. Sci., 1967, 56, 970-973 (http://lego.chemistry.tripod.com/Journals/TF-Amph.djvu)
Trifluromethyl analogs of amphetamine and norephedrine
Roger M. Pinder, Alfred Burger

Arzneimittel-Forschung , 1970, 20, 245-246 (http://lego.chemistry.tripod.com/Journals/CN-Amph.djvu)
m- and p-Hydroxy-1-cyanophenethylamine
Roger M. Pinder, Alfred Burger, E. J. Ariens

Thanks Dioulasso! The link is now fixed.

The tendency is to push it as far as you can

dioulasso
(Newbee)
01-29-04 01:22
No 485188
      Lego, you accidentally posted the Arz-Forsch.

Lego, you accidentally posted the Arz-Forsch. paper again in place of the J. Pharm. Sci. one !

" Unorthodox cooking, illicit cooking. A bit of real science, in fact. "

Antoncho
(Official Hive Translator)
01-29-04 10:51
No 485264
      GHB pharmacology

I hope i'm in the right forum - there's no "Wanted refs" thread in General smile

So... Could anyone please get these highly interesting articles, if he/she happens to come by them?

Tunnicliff G.
"Sites of action of gamma-hydroxybutyrate (GHB)--a neuroactive drug with abuse potential."
Journal of toxicology. Clinical toxicology. 1997; 35(6): 581-90.
Medline (PMID=9365423)

Antoncho

7is
(Stranger)
01-30-04 01:01
No 485399
      Halpern JH: The use of hallucinogens in the...

The use of hallucinogens in the treatment of addiction
Halpern, J.H.
Addict Res 4, 177–189 (1996)

That is not a chemistry article, but I haven´t been able to find it, so I thought I would ask for it here. If anyone could get it I would bee very thankful.

lugh
(Moderator)
01-31-04 10:20
No 485666
      Retrieved Articles

The following articles were retrieved:

For Chimimanie:
Identification of new secondary metabolites of methoxyphenamine in man.,
McKay, G.; Cooper, J. K.; Hawes, E. M.; Roy, S. D.; Midha, K. K.
Xenobiotica (1983), 13(4), 257-64.

Abstract
Metabolites of methoxyphenamine (I) [93-30-1] were examd. in the urine of healthy human volunteers. The metabolites were sepd. by gas liq. chromatog. and identified by comparison of their chromatog. and mass-spectrometric behaviors with those of authentic synthetic compds. 5-Hydroxy-2-methoxy-N-methylamphetamine [61866-76-0], a metabolite previously identified by indirect methods, was conclusively identified by comparison with the now-available authentic synthetic material. In addn., 3 new metabolites of methoxyphenamine were identified 5-hydroxy-2-methoxyamphetamine [87835-15-2], 2-methoxyphenylacetone [5211-62-1] and 5-hydroxy-2-methoxyphenylacetone [87835-16-3].
____ ___ __ _

For Rhodium:
The formation and chemical properties of diastereomeric 1,2-Dimethyl-3-phenylaziridine
T. Taguchi & M. Kojima
Chem. Pharm. Bull. 7, 103-107 (1959)


The Synthesis of ¹⁴C-diethylamine and lysergic acid diethylamide
Journal of Labelled Compounds and Radiopharmaceuticals 10:(2), 207 (1974)

A Study of the Precursors, Intermediates and Reaction By-Products on the Synthesis of MDMA and its Application to Forensic Drug Analysis.
Renton, R.J., Cowie, J.S. and Oon, M.C.
Forensic Science International 60, 189-202 (1993)

Chemistry is our Covalent Bond

Zamboni
(Stranger)
02-02-04 00:35
No 485919
      Dissertationes Pharmaceuticae

Can anyone get this article? This Abstract was found in Chemical Abstracts 61, 4145b (1964)

Dissertationes Pharmaceuticae 15(4), 419-426 (1963)
IR spectra in the 1-14µ range of apiole, 1,2,3,6-tetramethoxy-4-allylbenzene, myristicin, etc. obtained from various essential oils are recorded and discussed.

_{Some things I found using Google:

Prace Komisji Nauk Farmaceutycznych Dissertationes Pharmaceuticae
Dissertationes Pharmaceuticae
http://www.if-pan.krakow.pl/pjp/986_1.htm

Polish Journal of Pharmacology and Pharmacy (1973-1992) (ISSN 0301-0244 POL)
Dissertationes Pharmaceuticae et Pharmacologicae (1966-1972) (ISSN 0012-3870 POL)
Dissertationes Pharmaceuticae (1954-1965) (ISSN 0301-1615 POL)
Dissertationes Pharmaceuticae (1949-1952) (ISSN 0477-4795 POL)

http://unionlist.sti.sci.eg/data/00013/00013835.htm}

Rhodium
(Chief Bee)
02-02-04 09:21
No 486019
User Picture       Cinnamic acids to nitrostyrenes?

A Nitro-Hunsdiecker Reaction: From Unsaturated Carboxylic Acids to Nitrostyrenes and Nitroarenes
Jaya Prakash Das, Pradipta Sinha, Sujit Roy
ChemInform, Vol. 34, Issue 3, 5 Mar 2003
DOI:10.1002/chin.200303068
____ ___ __ _

Magnesium/Ammonium Formate Promoted Rapid, Low-Cost and Selective Reduction of Nitro Compounds.
G. R. Srinivasa, K. Abiraj, D. Channe Gowda
ChemInform, Vol. 35, Issue 8, 28 Jan 2004
DOI:10.1002/chin.200408055

^{The Hive - Clandestine Chemists Without Borders}

azole
(One Remarkable HyperLab Bee)
02-02-04 13:04
No 486043
      PTC alkylation of hydroquinone

Synthesis of 1,4-bis(2-chloroethoxy)benzene by PTC alkylation of hydroquinone (ref. #23 from Dihydrobenzofuran Analogues of Hallucinogens. 3. (https://www.rhodium.ws/pdf/nichols/nichols-dihydrobenzofuran-3-fly.pdf)):

Synthesis of Concave Receptors Derived from Diphenylglycoluril.
Sijbesma, R. P.; Nolte, R. J. M.
Recl. Trav. Chim. Pays-Bas 1993, 112, 643-647.

Lego
(Hive Bee)
02-04-04 17:14
No 486341
User Picture       For azole

Recl. Trav. Chim. Pays-Bas, 1993, 112, 643-647 (http://lego.chemistry.tripod.com/Journals/quinone-PTC.djvu)

Sorry for the bad quality, if you really need the left margin Lego will copy it again. The experimental details of the compound can bee read.

The tendency is to push it as far as you can

lugh
(Moderator)
02-04-04 21:53
No 486401
      For Murmur

From Post 485061 (murmur: "1-(Dimethylamino)-2-bromopropane HBr", Novel Discourse)

M.Lefler, R.Adams. J.Am.Chem.Soc. 59, 2252 (1937)

and the English translation of Zh.Org.Khim. 19(11), 2288-2294 (1983):

J.Org.Chem.USSR (Engl.Transl.) 1997-2002 (1983)

smile

Chemistry is our Covalent Bond

Lego
(Hive Bee)
02-04-04 23:53
No 486432
User Picture       Some Synth. Comm. articles again...

Preperation of methyl-MDA precursors, as mentioned in J. Med. Chem., 1985,28, 1273-1279 (ref. 17 and 18)
Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse)

Sinhababu, A. K.; Borchardt, R. T.
Synth. Comm., 1983, 13, 677-

Sinhababu, A. K.; Borchardt, R. T.
Synth. Comm., 1982, 12, 983-

The tendency is to push it as far as you can

Vitus_Verdegast
(Hive Addict)
02-21-04 22:27
No 490214
User Picture       wanted, alive and well :)

As posted in Post 475500 (Nicodem: "Modifications on the side chain (again)", Novel Discourse) :

“The alpha-methyl group of amphetamine itself can be replaced by allyl, ethyl, or ethynyl groups of electron-donating character, without deleterious effects on centrally-mediated actions [1,2], but replacement by electron-withdrawing groups, such as cyano [3] or trifluoromethyl [4], abolishes amphetamine-like properties.”

[1] Burger, Zimmermann, Ariens (1966), J. Med. Chem. , 9, 469. [Retrieved]
[2] Shamano, Hitchens, Goldstein, Beiler (1968), Arch. int. Pharmacodyn. Ther. , 172, 251.
[3] Pinder, Burger, Ariens (1970), Arzeim.-Forsch. , 20, 245. [Retrieved]
[4] Pinder, Burger (1967), J. Pharm. Sci., 56, 970. [Retrieved]

If anybody can find and post them, these are the refs for the phenoxyethylamines:
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 4 (1969), 334.
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 5 (1970), 337.
(European J. of Med. Chem. stil had the title Chim. Ther. in those times)
Rougeul, A.; Laval. med., 40 (1969), 37.
Rougeul, A. and Verdaux, J.; Rev. Can. Biol., 31 (1972), 49.

"A short and efficient preparation of alpha,p-dimethylstyrene from citral."
Barton, Derek H. R. / Parekh, Shyamal I.
Synthetic communications 19, 19, 3353-3361 (1989)

Related article:

"The effect of hydrogen ion concentration and oxygen upon the acid catalysed cyclization of citral"

Tetrahedron Vol 26, Issue 20 (1970) p. 4901-4913
DOI:10.1016/S0040-4020(01)93142-4

http://www.movieconnection.it/schede/nosferatu.jpg

Purepacker
(Stranger)
02-27-04 21:03
No 491498
User Picture       Traces of metals in Ecstacy tablets

Could someone retrieve the following article?

Traces of metals in Ecstacy tablets
S. Comment et. al.,
Probl. Forensic Sci., 66, p. 131 (2001)

I´m not suffering from Magnon´s Syndrome...It just itches!

Rhodium
(Chief Bee)
03-05-04 01:46
No 493054
User Picture       For Ganesha:

The Ho article was published in Journal of Medicinal Chemistry and not in Nature.

Amphetamine Analogs. II. Methylated Phenethylamines
Beng T. Ho, et. al.
J. Med. Chem. 13, 134-135 (1970) (https://www.rhodium.ws/pdf/amph-analog-2.pdf)
____ ___ __ _

Psychotropic Phenylisopropylamines derived from Apiole and Dillapiole
Alexander T. Shulgin
Nature 215, 1494-95 (1967) (https://www.rhodium.ws/chemistry/dmmda.shulgin.html)
____ ___ __ _

Structure-Activity Relationships of One-Ring Psychotomimetics
Alexander T. Shulgin, Thornton Sargent, Claudio Naranjo
Nature 221, 537-541 (1969) (https://www.rhodium.ws/djvu/shulgins.djvu)

Abstract
Human dose-response relationships for psychotomimetic phenethylamines: An isopropylamine side chain and triple methoxy substitution provide optimum activity. Available data suggest possible structures for the hypothetical psychotogen of schizophrenia.

^{The Hive - Clandestine Chemists Without Borders}

Ganesha
(Stranger)
03-05-04 13:13
No 493143
      Shulgin

The replacement of two adjacent methoxy groups with a methylenedioxy ring generally increases potency...
I would be grateful if someone could supply me with this paper covering the details:

C. Naranjo, A. T Shulgin, and T. Sargent, Med. Pharmacol. Exp., 17,359 (1967)

Bibliography data on the latter, found by Major_Armstrong:
Medicina et pharmacologia experimentalis
Basel ; New York : S. Karger, 1965-1967, 6 v. : ill. ; 26 cm, Vol. 12, no. 1-v. 17, no. 6.
[sup]See: http://www.scd.univ-rennes1.fr/sante/perab_m.html%5B/sup]

Additional, much wanted paper is:

Psilocybin induces schizophrenia-like psychosis in humans via a serotonin-2 agonist action.
Vollenweider, F. X., Vollenweider-Scherpenhuyzen, M. F., Babler, A., Vogel, H., & Hell, D.
NeuroReport 9, 3897–3902 (1998)

'I' am a crowd, obeying as many laws As it has members. Chemically impure Are all 'my' beings.

azole
(A Truly Remarkable HyperLab Bee)
03-05-04 13:48
No 493149
      Retrieved Refs:

For Ruthenium:
(the article was also mentioned in
Post 422033 (Vitus_Verdegast: "R-T articles that might be interesting", Methods Discourse))

The Reimer-Tiemann Reaction, Enhanced by Ultrasound
John C. Cochran and Margaret G. Melville
Synth. Commun., 1990, 20(4), 609-616.

For Nicodem:
V. M. Rodionov, E. V. Machinskaya, and V. M. Belikov
Zh. Obshch. Khim., 18, 917-920 (1948) (in Russian).
Abstract
   Ethyl nitroacetate was obtained from acetoacetic ester by nitrosation followed by oxidation with dichromate / sulfuric acid in 60% overall yield.

Translation coming soon.

For Ganesha:

Post 492921 (azole: "<MMDA> Shulgin, Nature, 201, 1120 (1964)", Novel Discourse)
____ ___ __ _

The Ethyl Homologues of [TMA-2]
A Shulgin
Nature, 11, 186 (1968)
Post 493254 (Ganesha: "<TMA-2> ethyl homologs of", Novel Discourse)
____ ___ __ _

The Psychotomimetic Properties of 3,4,5-Trimethoxyamphetamine.
A. T. Shulgin, S. Bunnell, and T. Sargent
Nature, 189, 1011-1012 (1961).
Post 493144 (azole: "<TMA> Shulgin, Nature, 189, 1011-2 (1961)", Novel Discourse)

moo
(Hive Bee)
03-09-04 03:44
No 493855
      It appears that the preparation of nitroethane

It appears that the preparation of nitroethane from sodium ethyl sulfate and sodium nitrite gives many people much worse yields (see Post 471717 (wolfram: "P2NP Question", Chemistry Discourse)) than to the authors of the literature preparation, reference number 4 in https://www.rhodium.ws/chemistry/nitroalkane.html. Here is an abstract and more proper reference for that preparation, it might be an interesting read. Unfortunately my libraries don't carry this journal so it would be nice if someone could get it.

Preparation of nitroethane.
Desseigne, Gerard; Giral, Henri.
Memorial des Poudres, 34, 49-53 (1952). Journal language unavailable.
CAN 49:4388 ISSN 0369-1535

Abstract
cf. C.A. 47, 10229b. Na Et sulfate (85% yield) is made by treating 1 mole 20% oleum with 2 moles ethanol at 45 Deg for 30 min. and neutralizing with Na2CO3. EtNO2 (42.6%) is made by treating 1.5 moles NaNO2 with 1 mole Na Et sulfate at 125-30 Deg in the presence of 0.0625 moles K2CO3.

_{fear fear hate hate}

lugh
(Moderator)
03-09-04 11:13
No 493924
      Article Uploaded

The article requested by moo:

Desseigne, Gerard; Giral, Henri.
Memorial des Poudres, 34, 49-53 (1952)

cool

Chemistry is our Covalent Bond

Vitus_Verdegast
(Hive Addict)
03-09-04 19:15
No 493996
User Picture       Gigantine

Preparation of gigantine
Chemistry & Industry (London) 1971, p. 578

http://www.movieconnection.it/schede/nosferatu.jpg

moo
(Hive Bee)
03-09-04 21:49
No 494030
      Thanks!

Yes, thank you for the ref. I appreciate the old literature you post here, not only because I appreciate old literature per se. wink If I may ask you, do you just have an access to a great library or have you managed to collect the most interesting references already during the years? I myself am blessed with a so called "antique library" and I like it very much.

_{fear fear hate hate}

azole
(A Truly Remarkable HyperLab Bee)
03-14-04 14:56
No 495043
      retrieved refs.

For Ganesha:

Deoxygenation of Some 3-Oxo-steroids by Chlorotrimethylsilane and Zinc
P. Hodge and M. N. Khan
J. Chem. Soc. Perkin Trans. I 1975, 809-811.

<Ketones are deoxygenated to olefins using Zn/Me₃SiCl.>

An Improved Synthesis of (±)-Dihydroactinidiolide
G. V. Subbaraju, M. S. Manhas and A. K. Bose
Tetrahedron Lett., 32(37), 4871-4874 (1991).

<A 3-hydroxylactone adsorbed on SiO₂ is dehydrated under MW irradiation.>

For Nicodem:

1-[3-(2-Alkoxyphenoxy)-3-phenylpropyl]piperazines and some related compounds
V. Valenta, M. Bartošová and M. Protiva
Collect. Czech. Chem. Commun. 46(5), 1280-1287 (1981).

Synthesis of α-functional nitrocompounds by the nitration of activated carbonyl derivatives in two-phase system
V. P. Kislyi, A. L. Laikhter, B. I. Ugrak, and V. V. Semenov
Izv. Akad. Nauk, Ser. Khim. 1994(1), 76-79 (in Russian).

Ethyl 2-nitroacetoacetate as a new synthon for ethoxycarbonylnitrile oxide
V. P. Kislyi, A. L. Laikhter, B. I. Ugrak, and V. V. Semenov
Izv. Akad. Nauk, Ser. Khim. 1994(1), 103-105 (in Russian).

For Vitus_Verdegast:

Total synthesis of (±)-gigantine
G. J. Kapadia, G. S. Rao, M. B. E. Fayez, B. K. Chowdhury and M. L. Sethi
Chemistry and Industry (London) 1970, 1593-1594.

Synthesis of the Tetrahydroisoquinoline Alkaloids (±)-Tepenine, Tehaunine, and (±)-O-Methylgigantine and Revised Structure of Gigantine
G. J. Kapadia, M. B. E. Fayez, M. L. Sethi, and G. Subba Rao
Chem. Commun. 1970, 856-857.

<Ref. 3 from the article below.>

Total synthesis of (±)-gigantine and its O-methyl ether
A. M. Choudhury
Chemistry & Industry (London) 1971, 578.

<An independent synthesis. Again, no experimental details are given.>

BTW, Vitus, do you still need the articles about cyclization of citral?

Ganesha
(Stranger)
03-16-04 14:32
No 495493
      Wanted

Nichols, D.E., and Glennon, R.A. Medicinal chemistry and structure-activity relationships of hallucinogens. In: Jacobs, B.L., ed. Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press, 1984. pp. 95-142.

Please, someone, if you have the copy, scan those pages and post!

'I' am a crowd, obeying as many laws As it has members. Chemically impure Are all 'my' beings.

7is
(Newbee)
03-16-04 20:17
No 495540
      For Ganesha

David E. Nichols, Alexander T. Shulgin and Donald C. Dyer
Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives
Life Sciences Volume 21, Issue 4 , 15 August 1977, Pages 569-576

Abstract
Octanol-water partition coefficients (log P) were determined for a series of substituted psychotomimetic phenethylamine derivatives. A relationship was established between log P, steric bulk in the paraposition and the ability to stimulate serotonin (5-HT) receptors in an in vitro sheep umbilical artery preparation. It appears that Log P values and in vitro activity in this preparation may be useful in predicting hallucinogenic potency in man.

Rhodium
(Chief Bee)
03-17-04 00:33
No 495592
User Picture       Figures for TLC Mesh Column Chromatography

Could anyone please get me the Supplementary Material (Figures etc.) to this article?

TLC Mesh Column Chromatography
Douglass F. Taber
J. Org. Chem. 47, 1351-52 (1982) (https://www.rhodium.ws/pdf/tlc.mesh.column.chromatography.pdf)

^{The Hive - Clandestine Chemists Without Borders}

azole
(A Truly Remarkable HyperLab Bee)
03-17-04 12:20
No 495701
      alpha,para-dimethylstyrene

For Vitus_Verdegast:

A short and efficient method for the preparation of α,p-dimethylstyrene from citral (1)
D. H. R. Barton and S. I. Parekh
Synth. Commun., 19(19), 3353-3361 (1989).

   Abstract: Acid catalysed cyclization of citral to give α,p-dimethylstyrene using chloranil as an oxidizing agent is reported. The important aspect of this transformation is the dehydration of intermediate piperitenol followed by dehydrogenation to furnish the target compound in 80.5% yield.

Nicodem
(Hive Bee)
03-17-04 14:17
No 495716
User Picture       For Ganesha

Lemaire, Jacob and Shulgin. Ring-substituted bete-methoxyphenylethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol. 37: 575-577 (1985).

Abstract:Four members of a new class of psychotomimetic agents have been synthesized and evaluated in man. These compounds, which incorporate beta-methoxy group onto a beta-phenylethylamine sidechain. arc the first reported psychotomimctics which are structural analogues of the neurotransmitter noradrenaline. These substances are more potent than the corresponding phenethylamines (lacking a beta-methoxy group) but less potent than the correspondingly substituted amphetamine derivatives.
_{Sorry for the low PDF quality but I had to use a digital camera due to some restrictions about photocopying in a certain library. But anyway, the experimental part was already OCRed by Post 413294 (GC_MS: "Ring-substituted beta-methoxyphenylethylamines", Methods Discourse)}

“The real drug-problem is that we need more and better drugs.” – J. Ott

Nicodem
(Hive Bee)
03-17-04 19:20
No 495771
User Picture       OK, I know...

...this time I ask nearly the impossible but anyway:
Nikolova M., Daleva L. Marinova V. Farmazia (Sofia) 19 (1969) 31.
and/or
Vasileva E., Natova L. Compt. Rend. Bulgaria 44 (1991) 37.
_{The papers are probably in Bulgarian but that is OK}

“The real drug-problem is that we need more and better drugs.” – J. Ott

dioulasso
(Hive Bee)
03-17-04 20:36
No 495782
      Here is the Romanian one

For Nicodem:

Ana Serpler -- BAZE MANNICH, DERIVAŢI AI PIPERAZINEI
Farmacia (Bucharest) 16, 1968, 617-620.

ENGLISH SUMMARY:

Ana Serpler -- PIPERAZINE DERIVATED MANNICH BASES. NOTE II. NEW
DERIVATIVES OF 4-(BENZOIL-ETHYL)-1-BENZOIL PIPERAZINE

Following studies carried out by the author previously, some Mannich
bases were synthetized, disubstituted aromatic derivatives of piperazine. In these,
the benzyl radical was maintained, as a substituent in one of the nitrogen atoms,
while in the second nitrogen atom alkyl-aryl-cetone chains were grafted as
alkyl substituents, alkyl-oxy, alkenyl-oxy or bromide in the para position on the
aromatic nucleus.
Eight new components were obtained that have not been mentioned in the
literature before.
The conditions were established for the preparation and the necessary
qnantitative estimations were carriled out, as well as spectral analysis in the
infra-red range.

The rest is in Romanian, but understanding it shouldnt be a problem with some knowledge of Italian...

" Unorthodox cooking, illicit cooking. A bit of real science, in fact. "

n00dle
03-20-04 14:22
      biosynth ref
(Rated as: off-topic)

Megatherium
(Hive Bee)
04-04-04 11:39
No 498988
      Mannich reaction on primary amines (Wiss Z Techn)

[The Mannich reaction on primary amines]
H.G.O. Becker, W. Ecknig, E. Fanghänel, S. Rommel
Wiss. Z. Techn., Vol. 11, p. 38 (1968) [In German]

Vitus_Verdegast
(Hive Addict)
04-04-04 13:25
No 499011
User Picture       syringaldehyde

This is a similar synthesis like the one described in Post 286983 (foxy2: "Hmmm, CO2????", Chemistry Discourse), which was unfortunately a Chinese journal:

The copper–carbon dioxide system, a new mild and selective catalyst for the methoxylation of non-activated aromatic bromides
D. Nobel

Journal of the Chemical Society, Chemical Communications, 1993, (4), 419 - 420
DOI:10.1039/C39930000419

Abstract
Copper when associated with carbon dioxide is a mild and selective catalyst for the methoxylation of numerous non-activated aromatic bromides.
^{Reactant: NaOMe; carbon dioxide; 3-bromo-4-hydroxy-5-methoxy-benzaldehyde
Product: 4-hydroxy-3,5-dimethoxy-benzaldehyde; carbonic acid monomethyl ester sodium-salt
Yield: 99 percent
Reagent: Cu(OH)₂CuCO₃
Solvent: methanol
Time: 3 hour(s)
Temperature: 125°C
Other Conditions: var. time; also without CO₂, other aromatic bromides

As posted in Post 475500 (Nicodem: "Modifications on the side chain (again)", Novel Discourse) :

“The alpha-methyl group of amphetamine itself can be replaced by allyl, ethyl, or ethynyl groups of electron-donating character, without deleterious effects on centrally-mediated actions [1,2], but replacement by electron-withdrawing groups, such as cyano [3] or trifluoromethyl [4], abolishes amphetamine-like properties.”

[1] Burger, Zimmermann, Ariens (1966), J. Med. Chem. , 9, 469. [Retrieved]
[2] Shamano, Hitchens, Goldstein, Beiler (1968), Arch. int. Pharmacodyn. Ther. , 172, 251.
[3] Pinder, Burger, Ariens (1970), Arzeim.-Forsch. , 20, 245. [Retrieved]
[4] Pinder, Burger (1967), J. Pharm. Sci., 56, 970. [Retrieved]

If anybody can find and post them, these are the refs for the phenoxyethylamines:
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 4 (1969), 334.
Julia, M. and de Rosnay; European Journal of Medicinal Chemistry, 5 (1970), 337.
(European J. of Med. Chem. stil had the title Chim. Ther. in those times)
Rougeul, A.; Laval. med., 40 (1969), 37.
Rougeul, A. and Verdaux, J.; Rev. Can. Biol., 31 (1972), 49.

"It is the declared policy of the US Government to create a Drug-Free America by 1995."}

azole
(A Truly Remarkable HyperLab Bee)
04-09-04 17:00
No 499913
      For Ganesha: Can. J. Chem...

For Ganesha:

Synthesis of anthracyclinones. Part 1. Regioselective alkylation of 5-hydroxyquinizarin.
L. M. Harwood, L. C. Hodgkinson, J. K. Sutherland, and P. Towers.
Can. J. Chem., 62, 1922-1925 (1984).

   1,4-Dimethoxybenzene was reacted with propionic acid in polyphosphoric acid (70°, 2 h) to give 2,5-dimethoxypropiophenone in 95% yield. Subsequent reduction (Zn/Hg - aq. HCl, reflux, 5 h) resulted in 2,5-dimethoxy-1-n-propylbenzene which was further acetylated with AcCl/AlCl₃ in CS₂ to give 2,5-dimethoxy-4-n-propylacetophenone.

Rhodium
(Chief Bee)
04-10-04 15:35
No 500072
User Picture       Mg reduction of Nitro groups + amphetamine

Could anyone fetch these two revolutionary articles by Channe Gowda, published back-to back in Ind. J. Chem?

Hydrazine/magnesium mediated cost-effective and selective reduction of nitro compounds
Srinivasa GR, Abiraj K, Gowda DC
Ind. J. Chem. Sect. B, 42(11), 2885-2887 (2003)

Abstract
Hydrazine aided catalytic transfer hydrogenation has been employed for the reduction of both aliphatic and aromatic nitro compounds to corresponding amines. The use of low-cost magnesium, as catalyst leads to high yields of amino compounds under ambient conditions of temperature and pressure. Many commonly encountered functional groups like ethene, nitrile, acid, phenol, halogen etc. are compatible with the present system.
____ ___ __ _

Magnesium/ammonium formate promoted rapid, low-cost and selective reduction of nitro compounds
Srinivasa GR, Abiraj K, Gowda DC
Ind. J. Chem. Sect. B, 42(11), 2882-2884 (2003)

Abstract
The reduction of nitro compounds, both aliphatic and aromatic into corresponding amines has been achieved at room temperature in good yields by employing ammonium formate in the presence of low cost magnesium powder. The hydrogenation is fast and selective in the presence of other sensitive functionalities such as halogens, -OH, -OCH3, -CN, -COOR, -COOH etc. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.

Wanted Amphetamine Syntheses:

Synthesis of beta-phenyl-isopropylamine
O.Y. Magidson and G.A. Garkuska
J. Gen. Chem. (USSR) 11, 339-343 (1941) [CA 35, 58695 (1941)]

A new method of 1-phenyl-2-aminopropane preparation
B.R. Bobranskii and Y.K. Drabik
J. Appl. Chem. (USSR) 14, 410-414 (1941) [CA 36, 2531⁹ (1942)]

Preparation of 2-phenylisopropylamine
F.M. Jaeger and J.A. van Dijk
Proc. Acad. Sci. Amsterdam, 44, 26-40 (1941) [CA 37, 6219 (1943)]

Reduction of phenylhydrazone-p-sulfonic acids
R. Fusco and L. Canonica
Chim. Ind. (Milan) 32, 208-210 (1950) [CA 45, 4645a (1951)]

^{The Hive - Clandestine Chemists Without Borders}

sYnThOmAtIc
(Stranger)
04-10-04 19:13
No 500092
      Reference retrieval please

Ozone concentration determination w/ aq. KI
Mudd, J. B.; Leavitt, R.; Ongun, A.; McManus, T. T.
Atmos. Environ. 1969, 3, 669.

azole
(A Truly Remarkable HyperLab Bee)
04-12-04 12:18
No 500337
      Retrieved refs.

For Rhodium:

Two independent syntheses of amphetamine from the pre-war Soviet Union, in Russian. Translation... maybe later.

Synthesis of β-Phenylisopropylamine (Phenamine)
O. Yu. Magidson and G. A. Garkusha
Zhurnal Obshchei Khimii (J. Gen. Chem. (USSR)), 11, 339-343 (1941).

PhCH₂COOH + Ac₂O (cat. AcONa) --> P2P (50-55%);
P2P + HCONH₂ --> N-formylamphetamine;
N-formylamphetamine + 40% H₂SO₄ --> amphetamine (50-55% from P2P);
separation of enantiomers via bitartrate salt.

A New Method for the Preparation of 1-Phenyl-2-aminopropane
B. R. Bobranskii and Ya. V. Drabik
Zhurnal Prikladnoy Khimii (J. Appl. Chem. (USSR)), 14, 410-415 (1941).

PhCH₂CN + EtOAc + 1 eq. EtONa --> PhCH(CN)COCH₃ (86%);
PhCH(CN)COCH₃ + aq. H₃PO₄, 150°C --> P2P (76%);
P2P + HCOONH₄ --> N-formylamphetamine;
N-formylamphetamine + aq. HCl --> amphetamine (56% from P2P).

Nicodem
(Hive Bee)
04-13-04 08:02
No 500528
User Picture       For Ganesha

This is not Schmidt,E. et al.; Chem.Ber.; 55; 1922; 1756 which therefore still remain wanted,
but it is from the same year, same journal, same subject and probably of the same interest to you:
(Uploaded file not existing)

“The real drug-problem is that we need more and better drugs.” – J. Ott

lugh
(Moderator)
04-13-04 11:26
No 500548
      Same Author(s)

Actually the above pages were also by the same author(s), here's the entire article, Ber 1529-1537 (1922)

(Uploaded file not existing)

wink

Chemistry is our Covalent Bond

Rhodium
(Chief Bee)
04-13-04 15:43
No 500583
User Picture       tetranitromethane nitration

For Ganesha:
_{Zur Kenntnis des Tetranitromethans, V. Mitteilung.}
Tetranitromethan als Nitrierungsmittel (II)
E. Schmidt, et. al.
Chem. Ber. 55, 1751-1759 (1922) (https://www.rhodium.ws/pdf/tetranitromethane.nitration-2.pdf)

Bonus: For yet another tetranitromethane nitration of propenylbenzenes, see the end of this document: https://www.rhodium.ws/chemistry/nitryliodide.html

^{The Hive - Clandestine Chemists Without Borders}

Ganesha
(Newbee)
04-13-04 23:25
No 500678
      Shulgin

Medicinal chemistry and structure-activity relationships of hallucinogens.
Nichols, D.E., and Glennon, R.A.
In: Jacobs, B.L., ed. Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press, 1984. pp. 95-142.

The replacement of two adjacent methoxy groups with a methylenedioxy ring generally increases potency...
I would be grateful if someone could supply me with this paper covering the details:

C. Naranjo, A. T Shulgin, and T. Sargent, Med. Pharmacol. Exp., 17,359 (1967)

Bibliography data on the latter, found by Major_Armstrong:
Medicina et pharmacologia experimentalis
Basel ; New York : S. Karger, 1965-1967, 6 v. : ill. ; 26 cm, Vol. 12, no. 1-v. 17, no. 6.
[sup]See: http://www.scd.univ-rennes1.fr/sante/perab_m.html%5B/sup]

GOVERNMENT IS ON YOUR SIDE + WATCH WAR ON TV + REPRODUCE + NO INDEPENDENT THOUGHT + OBEY

Rhodium
(Chief Bee)
04-14-04 17:32
No 500815
User Picture       Retrieved References & Friendly Advice

For Lego:
Selective hydrogenation of aromatic and aliphatic nitro compounds by hydrogen transfer over magnesia
Kijenski, J.; Glinski, M.; Wisniewski, R.; Murghani, S.
Studies in Surface Science and Catalysis 59 (Heterog. Catal. Fine Chem. 2), 169-76 (1991) (https://www.rhodium.ws/pdf/nitro.reduction.mgo.pdf)

Abstract
The possibility of using aliph. alcs. as hydrogen donors for the catalytic transfer redn. of nitro group over MgO was examd. Catalytic hydrogen transfer was found to be effective and selective for redn. of nitrobenzene, 4-nitrotoluene, 4-chloronitrobenzene, 4-nitro-m-xylene, b-nitrostyrene, 3-nitrobenzaldehyde, 1-nitropropane, and 1-nitrobutane. Conversion of starting nitro compd. into desired product depended on the alc. used as a donor. Adsorption of reactant and catalyst deactivation were studied by ESR. New aspects of a role of one-electron donor sites in hydrogen transfer over MgO were demonstrated.
____ ___ __ _

For Armageddon:
Indium/Ammonium Chloride Mediated Selective Reduction of Aromatic Nitro Compounds: Practical Synthesis of 6-Amino-Chrysene
Bimal K. Banik, Michelle Suhendra, Indrani Banik, and Frederick F. Becker
Synthetic Communications 30(20), 3745-3754 (2000) (https://www.rhodium.ws/pdf/indium.nitro.reduction.pdf)

Abstract
Reduction of aromatic and heteroaromatic nitro compounds to the corresponding amino compounds was achieved by indium/ammonium chloride induced reaction in aqueous ethanol. This method was extended for the preparation of large quantities of 6-aminochrysene in excellent yield.
____ ___ __ _

Ganesha:

Instead of pursuing those ancient articles for benzaldehyde preparation, I'd like to direct you towards the much more modern references linked in the following threads:

Post 479855 (dioulasso: "Substituted Mandelic acids", Chemistry Discourse)
Post 459724 (moo: "Oxidation of mandelic acid to benzaldehyde etc.", Methods Discourse)
Post 328397 (demorol: "Piperonal synthesis", Novel Discourse)

^{The Hive - Clandestine Chemists Without Borders}

azole
(A Truly Remarkable HyperLab Bee)
04-14-04 18:25
No 500823
      For Ganesha:

For Ganesha:

An article in Russian, just for archiving purposes.

Synthesis of Vanillin
G. V. Chelintsev and B. N. Rodnevich
Zhurnal Prikladnoy Khimii (J. Applied Chem. (USSR)), 8, 909-911 (1935).

   Patented methods of vanillin synthesis are reviewed. Optimized conditions for the synthesis of vanillin from guaiacol and glyoxylic acid are given. Electrosynthesis of glyoxylic acid from oxalic acid is described.

Old (1868 - 1901) Berichte volumes can be viewed free of charge at http://gallica.bnf.fr

Rhodium
(Chief Bee)
04-20-04 15:24
No 501813
User Picture       For Armageddon

Thiamin Analogs. IV. 4(5)-Methyl-5(4)-(beta-hydroxyethyl)-imidazole
Sidney W. Fox, Herbert Sargent, Edwin R. Buchman
J. Am. Chem. Soc. 67, 496-497 (1945)

(Reduction of an oxime to an amine using Sn/SnCl₂/HCl)

^{The Hive - Clandestine Chemists Without Borders}

josef_k
(Hive Bee)
04-21-04 20:10
No 502121
      quaternary N-methyl-4-piperidone methiodide

Could someone get these articles drone mentioned on the reaction of the quaternary N-methyl-4-piperidone methiodide with amines to get N-substituted 4-piperidones.

Chem. Heterocycl. Compd. 21(12) 1327

Also, in an article I saw they alkylated 4-piperidone pyrrolidine enamine with allylbromide to get 3-allyl-4-piperidone but they didn't give reaction details or references. That kind of reaction would be useful for making 3-methyl piperidones.

Chem. Heterocycl. Compd. 21(12): 1362

Ganesha
(Newbee)
04-22-04 23:29
No 502336
      iodination

Paper is from '92, hence too old to be found online for free.

acetophenone --> a-iodoacetophenone in 86% yield @ R.T w/ H2SO4/KI/KIO3 in acetic:

Okamoto, Tsuyoshi; Kakinami, Takaaki; Nishimura, Tetsuo; Irwan-Hermawan; Kajigaeshi, Shoji; Bull.Chem.Soc.Jpn.; 65; 6; 1992; 1731-1733.

Ok, thanks!

'I' am a crowd, obeying as many laws As it has members. Chemically impure Are all 'my' beings.

Lego
(Hive Bee)
04-23-04 18:47
No 502510
User Picture       PTC & diazonium chemistry

Applications of phase transfer catalysis to arenediazonium cation chemistry.
Gokel, George W.; Ahern, Michael F.; Beadle, James R.; Blum, Lorna; Korzeniowski, Stephen H.; Leopold, Ahuva; Rosenberg, David E.
Dep. Chem., Univ. Miami, Coral Gables, FL, USA.
Israel Journal of Chemistry (1985), 26(3), 270-6.

Abstract
A review with 54 refs. on the applications of phase-transfer catalysis to arenediazonium cation in coupling, redn., halogenation, arylation and cyclization reactions.

The tendency is to push it as far as you can

Vitus_Verdegast
(Hive Addict)
04-27-04 21:52
No 503376
User Picture       β-Phenoxyethylamines & AMT from Isatin

[The pursuit of AMT from isatin]
Joshi, K.C. et al, Pharmazie 39, 153 (1984)

_{Summary:
3-Methyleneoxindoles can be selectively reduced at the C=C double bond using sodium dithionite in aq. ethanol.
Isatylideneacetones are reduced to the corresponding 3-acetonyloxindoles in 57-92% yield.}

_{As posted in Post 475500 (Nicodem: "Modifications on the side chain (again)", Novel Discourse):}

β-Phenoxyethylamines:

Julia, M. and de Rosnay; Eur. J. Med. Chem. (Chim. Therap.), 4, 334 (1969)
Julia, M. and de Rosnay; Eur. J. Med. Chem. (Chim. Therap.), 5, 337 (1970)
Rougeul, A. and Verdaux, J.; Rev. Can. Biol., 31, 49 (1972)
Rougeul, A.; Laval. Med., 40, 37 (1969)

"It is the declared policy of the US Government to create a Drug-Free America by 1995."

7is
(Newbee)
04-29-04 14:13
No 503747
      GHB vs. GBL

Improved pharmacological activity via pro-drug modification: comparative pharmacokinetics of sodium gamma-hydroxybutyrate and gamma-butyrolactone
Lettieri J, Fung H-L
Research Communications in Chemical Pathology and Pharmacology 1978, 22(1)107-118

Abstract
Although gamma-butyrolactone (GBL) rapidly converts to gamma-hydroxybutyrate (GHB) in vivo, the lactone gave significantly more prolonged hypnotic effects than GHB when equimolar doses were compared both parenterally and orally in rats. Plasma drug concentrations were higher after GBL administration through both routes, consistent with the observed differences in the pharmacological activity of these two compounds. Oral GBL was absorbed much faster than oral GHB, with the dual effects of decreasing potential first-pass metabolism and elevating plasma drug concentrations to the region where capacity-limited elimination is operative. Parenteral GBL produced a slower initial drug plasma clearance than parenteral GHB. In spite of the rapid metabolism of GBL to GHB, the apparent tissue distribution of these two compounds may be different.

7is
(Newbee)
05-05-04 23:19
No 505131
      for josef_k

Enamines: recent advances in synthetic, spectroscopic, mechanistic, and stereochemical aspects––I
Peter W. Hickmott
Tetrahedron (1982) 38(14): 1975-2050

Here is second part too.

Enamines: recent advances in synthetic, spectroscopic, mechanistic, and stereochemical aspects––II
Peter W. Hickmott
Tetrahedron (1982) 38(23): 3363-3446

java
(Hive Bee)
05-09-04 18:27
No 506027
      Hydrogenolysis of alcohols

Hydro-De- Hydroxylation or Dehydroxylation

ROH + H2 ------>(catalyst)----->   RH

Synthesis 32,1981
Morita,T.; Okamoto Y.; Sakurai, H.

*An indirect reduction that can be done in one step involves the treatment of the alcohol (primary, secondary or benzylic ) with NaI, Zn. and Me3SiCl . In this case the alcohol is first converted to the iodide, which is reduced.

*see. March's 5th ed. pg.527

We're all in this world together,
http://www.aztlan.net

moo
(Hive Bee)
05-10-04 14:14
No 506217
      Aromatic hydroxylation with H2O2 and Cu(NO3)2

For psyloxy:

Aromatic hydroxylation by a new cupric nitrate-H2O2-phosphate buffer system.
Nasreen, Aayesha; Adapa, Srinivas R.
Organic Preparations and Procedures International, 32(4), 373-376 (2000). Journal written in English.
CAN 133:335049 ISSN 0030-4948

Abstract
The title system was effective in converting arom. compds. to phenols in high yields. The reagents are easily handled and inexpensive, and the procedure is ecofriendly with high regioselectivity.

_{fear fear hate hate}

Rhodium
(Chief Bee)
05-10-04 16:44
No 506246
User Picture       For Java

Mild Conversion of Alcohols to Alkyl Halides Using Halide-Based Ionic Liquids at Room Temperature
Ren, R. X.; Wu, J. X., Org. Lett. 3(23), 3727-3728 (2001)
Supporting Information (http://pubs3.acs.org/acs/journals/supporting_information.page?in_coden=orlef7&in_volume=3&in_start_page=3727)

Articles from Synthesis can you retrieve yourself, see Post 363228 (Rhodium: "Free Online Chemistry & Medicinal Journals", Novel Discourse)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
05-22-04 04:56
No 508725
User Picture       Wanted: Shulgin Publications

Experientia 19, 127 (1963) (TMA Analogs + LAH Nitroalkene reduction byproduct)
Experientia 20, 366-9 (1964) (Methoxy-3,4-Alkoxy-Amphetamines)

^{The Hive - Clandestine Chemists Without Borders}

azole
(A Truly Remarkable HyperLab Bee)
05-26-04 14:30
No 509740
      For Rhodium:

For Rhodium:

Preparation of homomyristicinic acid
G. Y. Moltrasio and D. Giacopello
Org. Prep. Proc. Int. 4(1), 13-18 (1972).

Examination of the essential oil from the fruits of parsley
S. A. Alimukhamedov, N. A. Maksudov, M. I. Goryaev, and F. S. Sharipova
Khim. Farm. Zh. 6(9), 15 (1972).
(journal written in Russian)

Abstract
   The essential oil obtained by steam distillation of crushed seeds of parsley at 2 atm pressure was separated into 2 fractions which were analysed by GC. The oil was shown to contain apiole (57.6%), myristicin (10.8%), allyltetramethoxybenzene (0.8%) and terpenes: α-pinene (9.1%), camphene (0.3%), sabinene (6.3%), α-terpinene (1.8%), limonene (3.1%), γ-terpinene (0.2%) and p-cymene (2.8%). The derivatives of phenols were characterized by oxidation into apiolaldehyde (m. p. 101-102 °C) and tetramethoxybenzoic (m. p. 85-86 °C) and myristicinic (m. p. 206-207 °C) acids.

   I pretty much disbelieve the whole article. The authors claim that they separated the essential oil of parsley into the "phenolic" fraction (myristicin, apiole, and allyltetramethoxybenzene) and the neutral fraction (various terpenes) by means of 5% solution of KOH as if there were phenolic hydroxyls in apiole etc. .

   The page number given for the other article (Khim. Farm. Zh. 6(8), 23 (1972)) is probably incorrect.

lugh
(Moderator)
05-28-04 09:26
No 510033
      Shulgin Articles Retrieved

As requested in Post 508725 (Rhodium: "Wanted: Shulgin Publications", Novel Discourse);

Experientia 19, 127 (1963) and Experientia 20, 366-9 (1964)

cool

Chemistry is our Covalent Bond

Rhodium
(Chief Bee)
05-30-04 15:50
No 510319
User Picture       For demorol: Dave Nichols Reductions

Nickel boride/hydrazine hydrate reduction of aromatic and aliphatic nitro compounds. Synthesis of 4-(benzyloxy)indole and alpha-alkyltryptamines.
David H. Lloyd, David E. Nichols
J. Org. Chem. 51(22), 4294-4295 (1986) (https://www.rhodium.ws/pdf/nichols/nichols-ni2b-hydrazine.nitro-reduction.pdf)

Abstract
Nickel boride and hydrazine hydrate are convenient reagents for the reduction of aromatic and aliphatic nitro compounds to the corresponding amines. The reductive cyclization of 2-(benzyloxy)-6-nitro-2'-piperidinostyrene to 4-(benzyloxy)indole and the reduction of several indole nitroalkanes to the corresponding alpha-alkyltryptamines are provided as examples.

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
06-01-04 15:42
No 510729
User Picture       Some retrievals & some bad news..

For Ganesha:

[4-Methoxyphenol --72%--> 2-Hydroxy-5-Methoxybenzaldehyde --61%--> 2,5-Dimethoxybenzaldehyde]
K. Y. Chu, J. Griffiths, D. Ward
J. Chem. Research (Miniprint), No. 10, pp 3701-3721 (1981)

____ ___ __ _

[Hydroquinone --benzylchloride--> p-benzyloxyphenol]
Billy L. Allwood, Billy L. et. al
J. Chem. Soc. Chem. Commun. 14, 1061-1064 (1987)

Armageddon:

_{W. Buth, F. Külz and K.W. Rosenmund, Chem. Ber., 72 (1939) p. 19-28
V. Hanus, K. Keres and J Cabák, Org. Mass Spectrom., 10 (1975) p. 448-454}

The above articles aren't useful. The german citation is an obituary over a chemistry professor, and the second one discusses mass spectrometry of benzaldehyde imines, and only devotes one line commenting on that P2P also forms imines which can be seen in a GC-MS.

Lego:

I think something is wrong with your citation T. Ho, Synth. Comm., 1972, 2, 702 - Volume 2 (1972) of Synth. Commun. has less than 500 pages if the bound book at my library is complete.

But I found Part II and III in Abramovitch's article series in my paper archive and posted them here: Post 510378 (Rhodium: "Abramovitch Tryptamine Syntheses", Tryptamine Chemistry)

^{The Hive - Clandestine Chemists Without Borders}

Ganesha
(Hive Bee)
06-01-04 21:21
No 510761
      ZzzZZzzZZzz

Thanks for the first high-yield-paper, it will come to use!

I fell asleep while trying to read the second... Am I blind or are they no details (other than yield and NMR data) on how to prepare the frikkin' mono-benzyloxy-compound from HQ and BzCl? Can someone take a look in ref. # 1 and ref. # 2 in that paper?

'I' am a crowd, obeying as many laws As it has members. Chemically impure Are all 'my' beings.

Lego
(Hive Bee)
06-01-04 21:36
No 510767
User Picture       The reference

The reference is from J. Med. Chem., 1982, 25, 908-913:

(9) T. Ho, Synth. Commun., 2, 702 (1972).

Perhaps this a classical example of reference typo frown or your libarian is cheating on you....

The tendency is to push it as far as you can

Rhodium
(Chief Bee)
06-03-04 18:46
No 511264
User Picture       More references of desire

Ephedrine Chemistry: Review
Monatsh. Chem. 41, 325 (1920)

^{The Hive - Clandestine Chemists Without Borders}

Ganesha
(Hive Bee)
06-04-04 13:55
No 511444
      Hallucinogen SAR

Medicinal chemistry and structure-activity relationships of hallucinogens.
Nichols, D.E., and Glennon, R.A.
In: Jacobs, B.L., ed. Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press, 1984. pp. 95-142.

'I' am a crowd, obeying as many laws As it has members. Chemically impure Are all 'my' beings.

SpicyBrown
(Hive Bee)
06-05-04 19:43
No 511659
      Attn demerol

Formylation of the dimethoxybenzenes using phosphorus oxychloride and N-methylformanilide
Armiger H. Sommers, R. J. Michaels, and Arthur W. Weston

J. Am. Chem. Soc., 74(21), 5546(1952)

-SpicyBrown

Kinetic
(Hive Bee)
06-06-04 12:50
No 511774
      Enormous PDF files

For Rhodium, with apologies for the enormity of the scanned PDF files (8.2 and 5.1MB respectively):

Active Amino Acids. V*⁵. Synthesis of Optically Active alpha-Aminoalcohols by the Reduction of alpha-Amino Acid Esters with Sodium Borohydride
Chem. Pharm. Bull., 13 (8), 995-1000 (1965)

Cupric Oxide as an Efficient Catalyst in Methylenation of Catechols
Chem. Pharm. Bull. 16 (3), 523-526 (1968)

Rhodium
(Chief Bee)
06-07-04 03:08
No 511877
User Picture       For Armageddon

Ammonium Salts of Aliphatic Carboxylic Acids
Saverio Zuffanti, J. Am. Chem. Soc. 63, 3123-3124 (1941)

^{The Hive - Clandestine Chemists Without Borders}

azole
(A Truly Remarkable HyperLab Bee)
06-07-04 15:52
No 511988
      retrieved refs.

For Rhodium:

Über Diastereomerie V). Diastereomerie und Krystallsymmetrie des Ephedrins
H. Emde und F. Spaenhauer
Helv. Chim. Acta, 13, 3-9 (1930).

For Ganesha:

Ueber Paraoxyphenol und einige vom Hydrochinon derivirende Aldehyde und Alkohole
A. Hantzsch
J. Prakt. Chem., <2>22, 460-476 (1880).

Reimer-Tiemann formylation of 4-ethoxyphenol (yield 40-45%).

Lego
(Hive Bee)
06-07-04 23:20
No 512079
User Picture       Sandmeyer

A novel metal promoter for the Sandmeyer reaction.
Anon. UK. CODEN: RSDSBB ISSN: 0374-4353. CAN 103:87565 AN 1985:487565
Research Disclosure (1985), 252 171.

Abstract
Fe²⁺ halide or Fe^o-Fe³⁺ system as a promoter for the Sandmeyer reaction, wherein Cu⁺ causes detrimental side effects in the case of Me-substituted or ortho-substituted arenediazonium salts, was discussed. The oxidn. of pendant Me groups was not evident in the Fe system and the reaction was applicable to a wide variety of functional groups. The Fe system is less expensive than Cu⁺ and more friendly environmentally.

The following reference is from J. Med. Chem., 1982, 25, 908-913:

(9) T. Ho, Synth. Commun., 2, 702 (1972).

Perhaps this a classical example of reference typo frown or your libarian is cheating on you....

The tendency is to push it as far as you can

azole
(A Truly Remarkable HyperLab Bee)
06-08-04 15:21
No 512200
      For synthon:

O-Monoalkylation of hydroquinone with alcohols
A. G. Rybin, A. V. Orlov, E. N. Zil'berman, M. Z. Barskova
Zh. Org. Khim., 27(9), 1828-1831 (1991).
(journal written in Russian)

4-Alkoxyphenols, ROC₆H₄OH. The method is based on Patent US4294991.
   a. (R = CH₃, C₃H₇, C₄H₉, i-C₄H₉).
   A thermostatted glass reactor equipped with a magnetic stirrer and a reflux condenser was loaded with hydroquinone (8 g), quinhydrone (3 g), an alcohol (ROH, 100 ml) and sulfuric acid (8 ml). The mixture was stirred at 70 °C for 20 min; the unreacted alcohol was evaporated; the residue was taken up in water (50 ml) and extracted with PhMe (2×50 ml). The combined extracts were fractionally distilled in a vacuum (5 mm Hg).
   b. (R = C₅H₁₁, C₆H₁₃, C₇H₁₅). The reactants were mixed as above, and the mixture was brought to boiling until the reactants dissolved completely. Then it was cooled, washed with water to remove the acid, and fractionated in a vacuum.
   All the phenols obtained were recrystallized from heptane.

R Yield, % m. p., °C

CH₃ 80 54-55

C₃H₇ 64.1 55-56

C₄H₉ 48.8 64-65

i-C₄H₉ 17.2 64-66

C₅H₁₁ 30.2 46-47

C₆H₁₃ 28.2 47-48

C₇H₁₆ 7.7 59-60

   Should I post the translation in the thread Post 267698 (Antoncho: "P-MeO-phenol from hydroquinone: part II", Novel Discourse)?

java
(Hive Bee)
06-09-04 01:42
No 512272
      A Simple Method for the Reduction of Carboxylic...

A Simple Method for the Reduction of Carboxylic Acids to Aldehydes or Alcohols Using H(2) and Pd/C.
Falorni M, Giacomelli G, Porcheddu A, Taddei M.
J Org Chem. 1999 Nov 26;64(24):8962-8964.

I've read Post 430441 (Lego: "Reduction of carboxylic acids to aldehydes", Novel Discourse) to the article , I would like the whole article

Also a related article on related article on reduction of COOH .
J. Organomet. Chem 367,1989,C12

and alternatives approaches,
Tetrahedron Lett. 39, 8153, 1998

Hydrogenation of Carboxylic Acids to Aldehydes...
Appl. Catal. 88, 1992
Yoikoyama, T

We're all in this world together,
http://www.aztlan.net

demorol
(Hive Bee)
06-09-04 09:52
No 512352
      Methoxylation article wanted

Esters are effective co-catalysts in copper-catalyzed methanolysis of aryl bromides
Patrice Capdevielle, and Michel Maumy
Tet. Lett. 1993, 34(6), 1007-1010

Abstract

Rate of copper(I)-catalyzed substitution of aryl bromides into methyl-aryl ethers by methoxide ion is greatly enhanced in presence of esters. Soluble copper(I) complexes 2, arising from tetrahedral adducts 1 of methoxide onto esters, are likely responsible for this improvement.

Graphical Abstract

Esters RCOOMe afford soluble copper(I) complexes in> 3M MeONa solutions, allowing facile methanolysis of aryl bromides:

(Uploaded file not existing)

Excerpt from this article was already posted by foxy2 in Post 275285 (foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse), but I would really like to read the whole paper. Thanks.

Rhodium
(Chief Bee)
06-09-04 11:11
No 512368
User Picture       For Demorol & Java

For Demorol:

I have already posted that article in Post 287999 (Rhodium: "ArBr + NaOMe -> ArOMe + NaBr", Methods Discourse) but I forgot to add correct reference data to that post. For future reference, I'll add a link to that PDF from Post 275285 (foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse)

For Java:

A Simple Method for the Reduction of Carboxylic Acids to Aldehydes or Alcohols Using H2 and Pd/C
Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M., J. Org. Chem. 64, 8962-8964 (1999)

____ ___ __ _

UTFSE! Tetrahedron Lett. 39, 8153, 1998 has already been posted in Post 464426 (Lilienthal: "acid chlorides to aldehydes with formic acid", Tryptamine Chemistry)
____ ___ __ _

Finally, is this last one really correct? It seems to deal with acyl fluorides...

Katalytische Reduktion von aromatischen Carbonsäurefluoriden zu Aldehyden
Rudolf Braden and Thomas Himmler, J. Organomet. Chem. 367(3), C12-C14 (1989)
DOI:10.1016/0022-328X(89)87061-5

Abstract
Aromatic acyl fluorides can be reduced to the corresponding aldehydes in the presence of palladium complexes. Polymethylhydrosiloxane (PMHS) gives better results than hydrogen.

^{The Hive - Clandestine Chemists Without Borders}

java
(Hive Bee)
06-10-04 00:17
No 512505
      the enantioselective Hydrogenation of .....

Rhodium....thanks for the assistance with the references they are appreciated.....java

The enantioselective hydrogenation of N-acyl dehydroamino acids

Topics In Catalysis5 (1-4): 3-23, 1998

DOI:10.1023/A:1019141717606

Abstract
The historical development of asymmetric hydrogenation of N-acyl dehydroamino acids and their derivatives is reported. Both homogeneous and heterogeneous catalysis are illustrated by selected examples. Catalysis by water soluble complexes and transfer hydrogenation are also treated in this review. The mechanism of catalytic hydrogenation, its elementary steps and the origin of enantioselection are discussed.

Just hold on to the thread...that keeps us going
http://www.chiapaslink.ukgateway.net/

Rhodium
(Chief Bee)
06-10-04 13:26
No 512579
User Picture       For Java

The enantioselective hydrogenation of N-acyl dehydroamino acids
Topics In Catalysis 5(1-4), 3-23 (1998)

Abstract
The historical development of asymmetric hydrogenation of N-acyl dehydroamino acids and their derivatives is reported. Both homogeneous and heterogeneous catalysis are illustrated by selected examples. Catalysis by water soluble complexes and transfer hydrogenation are also treated in this review. The mechanism of catalytic hydrogenation, its elementary steps and the origin of enantioselection are discussed.

^{The Hive - Clandestine Chemists Without Borders}

Kinetic
(Hive Bee)
06-12-04 10:42
No 512950
      Related patent

Hi Nicodem smile

You might be interested to know that one of the authors of the study, Guilio Maffii, has taken out a patent on 3-phenylazetidine and its analogues:

Patent GB872446

pericles
(Newbee)
06-13-04 21:59
No 513204
      Shulgin 5-MeO-DIPT article

Someone must have access to Communications in Psychopharmacology. I'd love to read this.

N,N-Diisopropyltryptamine (DIPT) and 5-Methoxy-N,N-Diisopropyltryptamine (5-MeO-DIPT). Two Orally Active Tryptamine Analogs with CNS Activity.
Shulgin AT, Carter MF.
Communications in Psychopharmacology 1980; 4():363-369

Rhodium
(Chief Bee)
06-14-04 08:51
No 513279
User Picture       GABA-B as anxiolytic/antidepressant target

Genetic and pharmacological evidence of a role for GABA(B) receptors in the modulation of anxiety- and antidepressant-like behavior.
Mombereau C, Kaupmann K, Froestl W, Sansig G, van der Putten H, Cryan JF.
Neuropsychopharmacology 29(6), 1050-62 (2004)

Although there is much evidence for a role of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA) in the pathophysiology of anxiety and depression, the role of GABA(B) receptors in behavioral processes related to these disorders has not yet been fully established. GABA(B) receptors are G-protein-coupled receptors, which act as functional heterodimers made up of GABA(B(1)) and GABA(B(2)) subunits. Using recently generated GABA(B(1)) -/- mice, which lack functional GABA(B) receptors, and pharmacological tools we assessed the role of GABA(B) receptors in anxiety- and antidepressant-related behaviors. In the light-dark box, GABA(B(1)) -/- mice were more anxious than their wild-type littermates (less time spent in the light; reduced number of transitions). GABA(B(1)) -/- mice were also more anxious in the staircase test. Conversely, acute and chronic treatment with GS39783, a novel GABA(B) receptor positive modulator, decreased anxiety in the light-dark box and elevated zero maze tests for anxiety. On the other hand, GABA(B(1)) -/- mice had decreased immobility (antidepressant-like behavior) in the forced swim test (FST). These behavioral effects are unrelated to alterations in locomotor activity. In confirmation of the genetic data, acute and chronic treatment with CGP56433A, a selective GABA(B) receptor antagonist, also decreased immobility in the FST, whereas GS39783 did not alter this behavior. Taken together, these data suggest that positive modulation of the GABA(B) receptor may serve as a novel therapeutic strategy for the development of anxiolytics, whereas GABA(B) receptor antagonism may serve as a basis for the generation of novel antidepressants.

Medline (PMID=15039762)
DOI:doi:10.1038/sj.npp.1300413

^{The Hive - Clandestine Chemists Without Borders}

java
(Hive Bee)
06-14-04 17:49
No 513349
      for Rhodium Genetic and pharmacological ...

Genetic and pharmacological evidence of a role for GABA(B) receptors in the modulation of anxiety- and antidepressant-like behavior.
Mombereau C, Kaupmann K, Froestl W, Sansig G, van der Putten H, Cryan JF.
Neuropsychopharmacology 29(6), 1050-62 (2004)

Just hold on to the thread...that keeps us going
http://www.chiapaslink.ukgateway.net/

psyloxy
(Hive Addict)
06-14-04 19:14
No 513358
User Picture       reaction of P2O5 with various metal salts...

reaction of P₂O₅ with various metal salts (research target: POCl₃ from P₂O₅)

H. Kolbe, Ann. d. chem. u. pharm., 103, 240 (1859)

--psyloxy--

java
(Hive Bee)
06-14-04 19:38
No 513363
      Articles by H.Kolbe.....

Psyloxy...I found this articles by Kolbe, perhaps the one you want is among this since I don't read the language......java

http://134.130.101.5/akhintermann/chemistry/Kolbe/Kolbe_main.htm

Just hold on to the thread...that keeps us going
http://www.chiapaslink.ukgateway.net/

java
(Hive Bee)
06-14-04 19:49
No 513364
      For Psyloxy, Pericles & Myself:

For Psyloxy:
I found this articles by Kolbe, perhaps the one you want is among this since I don't read the language......java

http://134.130.101.5/akhintermann/chemistry/Kolbe/Kolbe_main.htm
____ ___ __ _

For Pericles:
I found this ....seems like the similar article....java

http://www.ijmt.net/7_1/7_1_3.html
____ ___ __ _

For Java:
DMTC that can be prepared directly from trichlorotriazine (cyanuric chloride)
Synth. Commun. 26, 3491 (1996)

DMTC= 2-chloro-4,6-dimethoxy[1,2,3]triazine

Just hold on to the thread...that keeps us going
http://www.chiapaslink.ukgateway.net/

java
(Hive Bee)
06-14-04 21:36
No 513389
      For Java

DMTC that can be prepared directly from trichlorotriazine (cyanuric chloride)
Synth. Commun. 26, 3491 (1996)

DMTC= 2-chloro-4,6-dimethoxy[1,2,3]triazine

Just hold on to the thread...that keeps us going
http://www.chiapaslink.ukgateway.net/

armageddon
(Hive Bee)
06-16-04 08:25
No 513751
      wanted

Hehehe....

"Isolation of Lysergol from Kaladana", C.I. Abou-Chaar and G.A. Digenis, Nature 212, 618 (1966)

BTW, the plant's full latin name is "Calonyction-Ipomoea (Choisy) Hallier f. nova species"....

THX A

"..ein Trank von unterschiedlicher Farbe, in ihm ist Heilung für die Menschen."

azole
(A Truly Remarkable HyperLab Bee)
06-16-04 17:03
No 513798
      For Nicodem:

Farmacologia della 3-fenilazetidina e di alcuni suoi derivati
G. Bianchi, G. Maffii
Il Farmaco, Ed. Sci., 21(2), 131-154 (1966).

Article in Italian. 473 kB (w/pictures).
Summary.
   The pharmacological properties (adrenergic) of substituted 3-phenylazetidines have been studied. 3-Phenylazetidine (L 2051) shows both excitatory and inhibitory effects on the β-sympathetic receptors: in small doses it produces increase in heart rate and contractile force; this effect is antagonized by dichloroisopropylarterenol. In high doses the drug reduces the effects of isopropylarterenol, and inhibits the inotropic action of epinephrine and arterenol. A biphasic action of L 2051 may be demonstrated also on the site of the α-receptors. The pharmacological activity of L 2051 may depend, at least in part, on histamine liberation. These various activities of L 2051 were found isolated in some of its derivatives.
   There is no synthetic part in the article. The derivatives of 3-phenylazetidine were synthesized according to the following publications:
Liebigs Ann. Chem., 626, 114 (1959);
ibid., 639, 157 (1961);
ibid., 647, 83 (1961).

	All 449 posts		Subject: Wanted references		Please login to post		Down