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

A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·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 th...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-09, Vol.75 (18), p.6290-6293
Main Authors: Zhang, Xiaoxiang, Teo, Wan Teng, Sally, Chan, Philip Wai Hong
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Molecular Structure
Organic chemistry
Preparations and properties
Propanols - chemistry
Stereoisomerism
Thiazoles - chemical synthesis
Thiazoles - chemistry
Thioamides - chemistry
Toluene - analogs & derivatives
Toluene - chemistry
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Description
Summary:A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101292r