Preparation of Thioamide Building Blocks via Microwave-Promoted Three-Component Kindler Reactions

Oleksandr I. Zbruyev, Nikola Stiasni, and C. Oliver Kappe*
Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria
J. Comb. Chem., 2003, 5 (2), pp 145–148
DOI: 10.1021/cc0200538
Publication Date (Web): December 6, 2002
Copyright © 2003 American Chemical Society
*

 To whom correspondence should be addressed. Phone:  +43-316-3805352. Fax:  +43-316-3809840. E-mail:  oliver.kappe@uni-graz.at.

Abstract

Abstract Image

A microwave-enhanced variation of the Kindler thioamide synthesis is introduced. Taking advantage of the sealed vessel capabilities of a dedicated single-mode microwave reacto,r a diverse selection of 13 aldehyde and 12 amine precursors was utilized in the construction of a representative 34-member library of substituted thioamides. The three-component condensations of aldehydes, amines, and elemental sulfur were carried out using 1-methyl-2-pyrrolidone (NMP) as solvent employing microwave flash heating at 110−180 °C for 2−20 min. A simple workup protocol allows the isolation of synthetically valuable primary, secondary, and tertiary thioamide building blocks in 83% average yield and >90% purity.

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History

  • Published In Issue March 10, 2003
  • Received July 15, 2002

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