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Hantzsch Thiazole Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr296

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Hantzsch Thiazole Synthesis. Comprehensive Organic Name Reactions and Reagents. 296:1330–1334.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The generation of thiazole derivatives by means of condensation of α-haloketones and thioamidesis referred to as the Hantzsch thiazole synthesis. This reaction takes place due to the strong nucleophilicity of the sulfur atom in thioamides or thioureas, and gives fantabulous yields for simple thiazoles but low yields for some substituted thiazoles, as of dehalogenation. It is a multistep reaction, and the intermediates have been isolated at low temperatures. This reaction has been changed to reduce the epimerization upon the formation of thiazole. Additionally, α-tosyloxy ketones have been used to replace α-haloketones for such reactions. It has wide application in the preparation of thiazole derivatives.

Keywords:

  • thio-ketone derivatives;
  • nucleophilicity;
  • cyclic intermediates;
  • epimerization