Bronsted Acid Catalyzed Cyclization of Propargylic Alcohols with Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles

被引：80

作者：

Zhang, Xiaoxiang ^{[1
]}

Teng, Wan ^{[1
]}

Teo, Sally ^{[1
]}

Chan, Philip Wai Hong ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637616, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 18期

关键词：

NUCLEOPHILIC SUBSTITUTIONS; CYSTOTHIAZOLE-A; SILYL ETHERS; C-C; CATIONS; LEWIS;

D O I：

10.1021/jo101292r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH center dot H2O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.

引用

页码：6290 / 6293

页数：4

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