4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 18, Pages 6290-6293

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo101292r

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Funding

  1. Nanyang Technological University [RG55/06]
  2. A*STAR, Singapore [092 1010 053]

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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.

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