Journal of Organic Chemistry 2010-09-17

Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of di- and trisubstituted thiazoles.

Xiaoxiang Zhang, Wan Teng Teo, Sally, Philip Wai Hong Chan

Index: J. Org. Chem. 75(18) , 6290-3, (2010)

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Abstract

A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·H(2)O-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.