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

J Org Chem. 2010 Sep 17;75(18):6290-3. doi: 10.1021/jo101292r.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Propanols / chemistry*
  • Stereoisomerism
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thioamides / chemistry*
  • Toluene / analogs & derivatives*
  • Toluene / chemistry

Substances

  • Alkynes
  • Propanols
  • Thiazoles
  • Thioamides
  • Toluene
  • propargyl alcohol
  • 4-toluenesulfinic acid