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Gewald Reaction

(Gewald Aminothiophene Synthesis, Gewald Synthesis of 2-Aminothiophene)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr267

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Gewald Reaction. Comprehensive Organic Name Reactions and Reagents. 267:1213–1216.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The route for synthesizing 2-aminothiophene involving a base-catalyzed condensation of a ketone having an active CH2 group with α-ketonitrile to form an olefin that cyclizes with sulfur is generally referred to as the Gewald reaction. This reaction has two major types of variants: a two-step synthesis and a one-pot synthesis. This reaction provides a route for thieno[2,3-d][1,3]-oxazin-4-ones, which is a useful moiety for the serine protease inhibitor. This reaction has also been modified to synthesize 2-aminothiophene with a substituent at the 3-, 4-, or 5-position.

Keywords:

  • thieno[2,3-d][1,3]-oxazin-4-ones;
  • 2-aminothiophenes;
  • olefin;
  • diethyl amine