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Digest: Pseudonitrosite Publications (1891-1998) Please login to post

Rhodium
(Chief Bee)
05-13-04 18:25
No 503727
User Picture Pseudonitrosite Publications (1891-1998)
(Rated as: excellent)

Here I will collect the all articles ever published on the topic of Pseudonitrosite adducts of propenylbenzenes, and any other article of significance to that topic (even if it mainly deals with pseudonitrosite derivatives of other alkenes). Please PM me if you know of any omissions (I estimate the current collection to comprise well over half of the above scope). I will add summaries of the most important findings in each of the articles (including a list of prepared compounds of interest) when I have the time. If you want to help out with this, send your summaries to me.

Recent Pseudonitrosite Articles (in English)

_{New NO-Donors with Antithrombotic and Vasodilating Activities, Part 21}
Pseudonitrosites and Other Azodioxides with Vicinal Electron Acceptors (Added 04-29-04):
Klaus Rehse and Martin Herpel
Arch. Pharm. Pharm. Med. Chem. 331(3), 111-117 (1998) (https://www.rhodium.ws/pdf/pseudonitrosite.no-donor.pdf)

Abstract
Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a–h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test, collagen). Four of them showed an IC₅₀ below 10 uM, 2a being the most active substance with an IC₅₀ = 2.1 uM. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound (18% inhibition in arterioles). The in vitro decomposition of 2a at 37°C gave NO and N₂O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron acceptors i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b,c).
____ ___ __ _

Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide (Added 04-19-04):
Teruaki Mukaiyama, Eiichiro Hata, and Tohru Yamada
Chemistry Letters 505-506 (1995) (https://www.rhodium.ws/pdf/alkene.nitration.no-1.pdf)

Abstract
Nitroolefins are conveniently prepared in high yields by nitration of olefins under an atmospheric pressure of nitric oxide at room temperature and subsequent treatment with acidic alumina.
____ ___ __ _

A Convenient Method for the Preparation of Nitro Olefins by Nitration of Olefins with Nitrogen Monoxide (Added 04-19-04):
Eiichiro Hata, Tohru Yamada, and Teruaki Mukaiyama
Bull. Chem. Soc. Jpn., 68, 3629-3636(1995) (https://www.rhodium.ws/pdf/alkene.nitration.no-2.pdf)

Abstract
Olefins with a terminal double bond or conjugated with aromatic nucleus are successfully nitrated into nitro olefins in good-to-high yields on treatment with nitrogen monoxide (NO) in 1,2-dichloroethane. Nitro alcohols formed as by-products are dehydrated to yield nitro olefins by the subsequent treatment with acidic activated alumina. By GC analysis, it was confirmed that an equimolar amount of nitrogen gas was evolved during the present nitration. A possible reaction pathway including the formation of nitro nitroso compounds, key intermediates, is described. The key intermediates are transformed into nitro olefins by reaction with nitrogen monoxide.

Other Pseudonitrosite Articles (in English or German)

Synthesis of 3-Methyl Isoquinolines (Added 04-29-04):
T. R. Govindachari, B. R. Pai
J. Org. Chem. 18, 1253-1262 (1953) (https://www.rhodium.ws/pdf/pseudonitrosite.25-meo.pdf)

2,5-Dimethoxy-propenylbenzene pseudonitrosite
____ ___ __ _

Über Pseudonitrosite, Nitroxime und Furoxane (Added 05-03-04):
Dieter Klamann, Wolfgang Koser, Peter Weyerstahl und Manfred Fligge
Chem. Ber. 98, 1831-1836 (1965) (https://www.rhodium.ws/pdf/pseudonitrosite.klamann.1965-ber1831.pdf)

Vintage Pseudonitrosite Articles (in German)

Ueber die Einwirkung der salpetrigen Säure auf einige ungesättigte Verbindungen der aromatischen Reihe. I. Mitteilung. (Added 04-29-04):
Angelo Angeli
Chem. Ber. 24, 3994-3996 (1891) (https://www.rhodium.ws/pdf/pseudonitrosite.angeli-1891.pdf)
____ ___ __ _

Ueber die Einwirkung der salpetrigen Säure auf einige ungesättigte Verbindungen der aromatischen Reihe. I. Mitteilung. (Added 04-29-04):
Angelo Angeli
Chem. Ber. 25, 1956-1963 (1892) (https://www.rhodium.ws/pdf/pseudonitrosite.angeli-1892.pdf)
____ ___ __ _

Zur Kenntniss der Pseudonitrosite latest addition (05-13-04):
H. Wieland
Ann. Chem. 329, 225-268 (1903) (https://www.rhodium.ws/pdf/pseudonitrosite.wieland.1903-ann225.pdf)
____ ___ __ _

Ueber die Additionsproducte von N₂O₃ und von NOCl (Added 05-03-04):
O. Wallach
Ann. Chem. 332, 305-336 (1904) (https://www.rhodium.ws/pdf/pseudonitrosite.wallach.1903-ann305.pdf)
____ ___ __ _

Zur Kenntnis der sogenannte Styrolnitrosite. Ueber eine neue Bildungsweise der untersalpetrigen Säure (Added 05-03-04):
H. Wieland
Chem. Ber. 36, 2558-2567 (1903) (https://www.rhodium.ws/pdf/pseudonitrosite.wieland.1903-ber2558.pdf)
____ ___ __ _

Über das Pseudonitrosit des Asarons (Added 04-29-04):
Viktor Bruckner
J. Prakt. Chem. 138, 268-274 (1933) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1933-jpc268.pdf)
____ ___ __ _

_{Über eine neue Umwandlung der Pseudonitrosite propenylhaltiger Phenoläther}
Eine neue Synthese von α-(Alkoxy-phenyl)-β-nitro-propanolen bzw. deren Methyläther (Added 04-29-04):
V. Bruckner und E. Vinkler
J. Prakt. Chem. 142, 277-290 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-jpc277.pdf)
____ ___ __ _

Über die Alkaliempfindlichkeit von α-(Alkoxy-phenyl)-β-amino- und -hydroxylamino-propanolen (Added 04-29-04):
Viktor Bruckner
J. Prakt. Chem. 142, 301-309 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-jpc301.pdf)
____ ___ __ _

_{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on α-arylierten β-Hydroxylamino- und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.}
I. Mitteilung. Methyl-isoeugenol- und Isosafrol-Derivate (Added 04-29-04):
Viktor Bruckner
Ann. Chem. 518, 226-244 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-ann226.pdf)
____ ___ __ _

_{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on α-arylierten β-Hydroxylamino- und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.}
II. Mitteilung. Isoeugenolderivate. (Added 04-29-04):
V. Bruckner und A. Krámli
J. Prakt. Chem. 143, 287-297 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-jpc287.pdf)
____ ___ __ _

_{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on α-arylierten β-Hydroxylamino- und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.}
III. Mitteilung. Anetholderivate (Added 04-29-04):
A. Krámli und V. Bruckner
J. Prakt. Chem. 148, 117-125 (1937) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1937-jpc117.pdf)
____ ___ __ _

Über eine neue Synthese von Ephedrinabkömmlingen (Added 04-29-04):
V. Bruckner und A. Krámli
Arch. Pharm. 273, 372-384 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-ap372.pdf)
____ ___ __ _

Über eine neue Synthese von Abkömmlingen des 3-Methyl-Isochinolins (Added 04-29-04):
V. Bruckner und A. Krámli
J. Prakt. Chem. 145, 291-300 (1936) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1936-jpc291.pdf)
____ ___ __ _

Über eine neue Synthese des α-[3,4-Dioxy-phenyl]-β-amino-propanols latest addition (05-13-04):
V. Bruckner und G. von Fodor
Chem. Ber. 76, 466-479 (1943) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1943-ber466.pdf)

^{The Hive - Clandestine Chemists Without Borders}

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			Digest: Pseudonitrosite Publications (1891-1998)		Please login to post


		Rhodium (Chief Bee) 05-13-04 18:25 No 503727				Pseudonitrosite Publications (1891-1998) (Rated as: excellent)
						Here I will collect the all articles ever published on the topic of Pseudonitrosite adducts of propenylbenzenes, and any other article of significance to that topic (even if it mainly deals with pseudonitrosite derivatives of other alkenes). Please PM me if you know of any omissions (I estimate the current collection to comprise well over half of the above scope). I will add summaries of the most important findings in each of the articles (including a list of prepared compounds of interest) when I have the time. If you want to help out with this, send your summaries to me. Recent Pseudonitrosite Articles (in English) _{New NO-Donors with Antithrombotic and Vasodilating Activities, Part 21} Pseudonitrosites and Other Azodioxides with Vicinal Electron Acceptors (Added 04-29-04): Klaus Rehse and Martin Herpel Arch. Pharm. Pharm. Med. Chem. 331(3), 111-117 (1998) (https://www.rhodium.ws/pdf/pseudonitrosite.no-donor.pdf) Abstract Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a–h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test, collagen). Four of them showed an IC₅₀ below 10 uM, 2a being the most active substance with an IC₅₀ = 2.1 uM. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound (18% inhibition in arterioles). The in vitro decomposition of 2a at 37°C gave NO and N₂O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron acceptors i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b,c). ____ ___ __ _ Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide (Added 04-19-04): Teruaki Mukaiyama, Eiichiro Hata, and Tohru Yamada Chemistry Letters 505-506 (1995) (https://www.rhodium.ws/pdf/alkene.nitration.no-1.pdf) Abstract Nitroolefins are conveniently prepared in high yields by nitration of olefins under an atmospheric pressure of nitric oxide at room temperature and subsequent treatment with acidic alumina. ____ ___ __ _ A Convenient Method for the Preparation of Nitro Olefins by Nitration of Olefins with Nitrogen Monoxide (Added 04-19-04): Eiichiro Hata, Tohru Yamada, and Teruaki Mukaiyama Bull. Chem. Soc. Jpn., 68, 3629-3636(1995) (https://www.rhodium.ws/pdf/alkene.nitration.no-2.pdf) Abstract Olefins with a terminal double bond or conjugated with aromatic nucleus are successfully nitrated into nitro olefins in good-to-high yields on treatment with nitrogen monoxide (NO) in 1,2-dichloroethane. Nitro alcohols formed as by-products are dehydrated to yield nitro olefins by the subsequent treatment with acidic activated alumina. By GC analysis, it was confirmed that an equimolar amount of nitrogen gas was evolved during the present nitration. A possible reaction pathway including the formation of nitro nitroso compounds, key intermediates, is described. The key intermediates are transformed into nitro olefins by reaction with nitrogen monoxide. Other Pseudonitrosite Articles (in English or German) Synthesis of 3-Methyl Isoquinolines (Added 04-29-04): T. R. Govindachari, B. R. Pai J. Org. Chem. 18, 1253-1262 (1953) (https://www.rhodium.ws/pdf/pseudonitrosite.25-meo.pdf) 2,5-Dimethoxy-propenylbenzene pseudonitrosite ____ ___ __ _ Über Pseudonitrosite, Nitroxime und Furoxane (Added 05-03-04): Dieter Klamann, Wolfgang Koser, Peter Weyerstahl und Manfred Fligge Chem. Ber. 98, 1831-1836 (1965) (https://www.rhodium.ws/pdf/pseudonitrosite.klamann.1965-ber1831.pdf) Vintage Pseudonitrosite Articles (in German) Ueber die Einwirkung der salpetrigen Säure auf einige ungesättigte Verbindungen der aromatischen Reihe. I. Mitteilung. (Added 04-29-04): Angelo Angeli Chem. Ber. 24, 3994-3996 (1891) (https://www.rhodium.ws/pdf/pseudonitrosite.angeli-1891.pdf) ____ ___ __ _ Ueber die Einwirkung der salpetrigen Säure auf einige ungesättigte Verbindungen der aromatischen Reihe. I. Mitteilung. (Added 04-29-04): Angelo Angeli Chem. Ber. 25, 1956-1963 (1892) (https://www.rhodium.ws/pdf/pseudonitrosite.angeli-1892.pdf) ____ ___ __ _ Zur Kenntniss der Pseudonitrosite (05-13-04): H. Wieland Ann. Chem. 329, 225-268 (1903) (https://www.rhodium.ws/pdf/pseudonitrosite.wieland.1903-ann225.pdf) ____ ___ __ _ Ueber die Additionsproducte von N₂O₃ und von NOCl (Added 05-03-04): O. Wallach Ann. Chem. 332, 305-336 (1904) (https://www.rhodium.ws/pdf/pseudonitrosite.wallach.1903-ann305.pdf) ____ ___ __ _ Zur Kenntnis der sogenannte Styrolnitrosite. Ueber eine neue Bildungsweise der untersalpetrigen Säure (Added 05-03-04): H. Wieland Chem. Ber. 36, 2558-2567 (1903) (https://www.rhodium.ws/pdf/pseudonitrosite.wieland.1903-ber2558.pdf) ____ ___ __ _ Über das Pseudonitrosit des Asarons (Added 04-29-04): Viktor Bruckner J. Prakt. Chem. 138, 268-274 (1933) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1933-jpc268.pdf) ____ ___ __ _ _{Über eine neue Umwandlung der Pseudonitrosite propenylhaltiger Phenoläther} Eine neue Synthese von α-(Alkoxy-phenyl)-β-nitro-propanolen bzw. deren Methyläther (Added 04-29-04): V. Bruckner und E. Vinkler J. Prakt. Chem. 142, 277-290 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-jpc277.pdf) ____ ___ __ _ Über die Alkaliempfindlichkeit von α-(Alkoxy-phenyl)-β-amino- und -hydroxylamino-propanolen (Added 04-29-04): Viktor Bruckner J. Prakt. Chem. 142, 301-309 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-jpc301.pdf) ____ ___ __ _ _{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on α-arylierten β-Hydroxylamino- und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.} I. Mitteilung. Methyl-isoeugenol- und Isosafrol-Derivate (Added 04-29-04): Viktor Bruckner Ann. Chem. 518, 226-244 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-ann226.pdf) ____ ___ __ _ _{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on α-arylierten β-Hydroxylamino- und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.} II. Mitteilung. Isoeugenolderivate. (Added 04-29-04): V. Bruckner und A. Krámli J. Prakt. Chem. 143, 287-297 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-jpc287.pdf) ____ ___ __ _ _{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on α-arylierten β-Hydroxylamino- und β-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.} III. Mitteilung. Anetholderivate (Added 04-29-04): A. Krámli und V. Bruckner J. Prakt. Chem. 148, 117-125 (1937) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1937-jpc117.pdf) ____ ___ __ _ Über eine neue Synthese von Ephedrinabkömmlingen (Added 04-29-04): V. Bruckner und A. Krámli Arch. Pharm. 273, 372-384 (1935) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1935-ap372.pdf) ____ ___ __ _ Über eine neue Synthese von Abkömmlingen des 3-Methyl-Isochinolins (Added 04-29-04): V. Bruckner und A. Krámli J. Prakt. Chem. 145, 291-300 (1936) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1936-jpc291.pdf) ____ ___ __ _ Über eine neue Synthese des α-[3,4-Dioxy-phenyl]-β-amino-propanols (05-13-04): V. Bruckner und G. von Fodor Chem. Ber. 76, 466-479 (1943) (https://www.rhodium.ws/pdf/pseudonitrosite.bruckner.1943-ber466.pdf) ^{The Hive - Clandestine Chemists Without Borders}