Cycloaddition of new N-unsubstituted azomethine ylides generated from N-(trimethylsilylmethyl)thioureas to electron-deficient olefins, acetylenes and aldehydes, synthetic equivalents of nonstabilized aminonitrile ylides

被引：21

作者：

Tsuge, O ^{[1
]}

Hatta, T

Tashiro, H

Kakura, Y

Maeda, H

Kakehi, A

机构：

[1] Sojo Univ, Dept Appl Chem, Ikeda, Kumamoto 8600082, Japan

[2] Shinshu Univ, Fac Engn, Dept Chem & Mat Engn, Wakasato, Nagano 3808553, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 39期

关键词：

azomethine ylides; 1,3-dipolar cycloadditions; nonstabilized aminonitrile ylide;

D O I：

10.1016/S0040-4020(00)00688-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The S-methylation of N-(trimethylsilylmethyl)thioureas and the subsequent desilylation of the silylmethyl group generates N-unsubstituted azomethine ylides having both methylthio and amino groups at the ylide carbon. These azomethine ylides undergo successful cycloaddition to electron-deficient olefins, acetylenes and aldehydes. As the methylthio group is eliminated under the reaction conditions to produce the corresponding pyrrolines, pyrroles and 2-oxazolines bearing the amino group at 2-position, these azomethine ylides can be synthetic equivalents of nonstabilized aminonitrile ylides that are otherwise relatively inaccessible. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7723 / 7735

页数：13