Reactions of Malonothioamide Derivatives with Azides

被引：15

作者：

Dianova, L. N. ^{[1
]}

Berseneva, V. S. ^{[1
]}

El'tsov, O. S. ^{[1
]}

Fan, Z. -J. ^{[2
]}

Bakulev, V. A. ^{[1
]}

机构：

[1] Ural Fed Univ, Ekaterinburg 620002, Russia

[2] Nankai Univ, State Lab Heteroorgan Chem, Tianjin 300071, Peoples R China

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2014年 / 50卷 / 07期

基金：

俄罗斯基础研究基金会; 对外科技合作项目（国际科技项目）;

关键词：

aryl azides; malonothioamides; 1,2,3-thiadiazoles; 1,2,3-triazoles; cyclocondensation; rearrangements; 1,2,3-TRIAZOLES; REARRANGEMENTS; CYCLIZATION;

D O I：

10.1007/s10593-014-1552-x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of primary and tertiary malonothioamides with aryl and sulfonyl azides can take place in three directions, depending on the nature of the thioamides and azides. Ethoxycarbonylthioacetamide reacts with aryl azides with the formation of ethyl 5-amino-1-aryl-1,2,3-triazole-4-carboxylates. In reaction with aryl azides tertiary thioamides of cyanoacetic acid form 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides, and in reaction with tosyl azide they form 5-amino-4-carboxamidino-1,2,3-thia-diazoles. Hypothetical mechanisms for the transformations are discussed.

引用

页码：972 / 978

页数：7

共 27 条

[1] Installation/Modulation of the Emission Response via Click Reaction [J].