Thiazole as leaving group. Thermal elimination from thiazolylketoses

被引：3

作者：

Dondoni, A ^{[1
]}

Marra, A ^{[1
]}

机构：

[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

HETEROCYCLES | 1999年 / 50卷 / 01期

关键词：

D O I：

10.3987/COM-98-8154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heating thiazolylketofuranoses and -ketopyranoses in refluxing toluene results in the elimination of thiazole and formation of the corresponding sugar lactones in nearly quantitative yield. The same reaction does not occur with 1-O-acetyl and 1-O-trimethylsilyl derivatives. Also model furyl- and thienylketofuranoses and various thiazolyl alcohols proved to be stable under the above thermolysis conditions. A possible mechanism of the observed thermolysis of thiazolylketoses involves the thiazolium 2-ylide as the actual leaving group.

引用

页码：419 / 426

页数：8

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