Unexpected 1,2,3-triazole formation in the reaction of diethylaluminum azide with α′-amino-α,β-unsaturated ketones

被引：14

作者：

Adamo, I ^{[1
]}

Benedetti, F ^{[1
]}

Berti, F ^{[1
]}

Nardin, G ^{[1
]}

Norbedo, S ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 51期

关键词：

3+2]cycloaddition; diethylaluminum azide; hydride transfer; 1H-1,2,3-triazole;

D O I：

10.1016/j.tetlet.2003.10.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Acyl-1H-1,2,3-triazoles are formed from diethylaluminum azide and alpha'-(N,N-dibenzylamino)-alpha,beta-unsaturated ketones by [3+2] cycloaddition of azide, followed by 1,5 hydride transfer to the beta carbon of the triazoline side chain and fragmentation of the tertiary amino group promoted by coordination of the latter to the Lewis acid. The structure of a triazole product is confirmed by X-ray crystallography. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9095 / 9097

页数：3

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