1-aza-2-azoniaallene salts: reactions with azomethines and other N-nucleophiles

被引：10

作者：

Al-Soud, YA ^{[1
]}

Shrestha-Dawadi, PB ^{[1
]}

Winkler, M ^{[1
]}

Wirschun, W ^{[1
]}

Jochims, JC ^{[1
]}

机构：

[1] Univ Konstanz, Fak Chem, D-78434 Constance, Germany

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 22期

关键词：

D O I：

10.1039/a804116d

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Azomethines undergo nucleophilic addition to 1-aza-2-azoniaallene salts 7 to furnish N-(azoalkyl)iminium salts (e.g. 10, 12, 13). With cyclic hydrazones such as pyrazole or indazole, heterocumulenes 7 afford bicyclic 1,2,4,5-tetrazinium salts (e.g. 14, 16), or simple N-adducts such as 15, 17. On the other hand, with open-chain hydrazones azinium salts 19 are formed. Benzotriazole and the aziridine 21 react with 1-aza-2-azoniaallene salts 7 to afford (azoalkyl)ammonium salts 20, 22. The heterocumulenes 7 undergo cycloaddition across the C=N double bond of the azirine 23 to furnish azirenotriazolium salts 25, while with the 1-aza-2-azoniaallene salt 3a the triazolium salt 28 was formed. The constitutions of compounds 22, 25a and 28 were confirmed by X-ray structural analyses.

引用

页码：3759 / 3766

页数：8

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