Reaction between (Z)-arylchlorooximes and α-isocyanoacetamides: a procedure for the synthesis of aryl-α-ketoamide amides

J Org Chem. 2014 Jul 3;79(13):6006-14. doi: 10.1021/jo5005444. Epub 2014 Jun 20.

Abstract

(Z)-Arylchlorooximes and α-isocyanoacetamides undergo a smooth reaction to produce 1,3-oxazol-2-oxime derivatives in good yields. Opening of the oxazole ring and deoximation reaction give a facile access to aryl-α-ketoamide amides, a class of privileged scaffolds in medicinal chemistry and important synthetic intermediates in organic chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Catalysis
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry*
  • Oximes / chemical synthesis*
  • Oximes / chemistry

Substances

  • 1,3-oxazol-2-oxime
  • Amides
  • Nitriles
  • Oxazoles
  • Oximes
  • 2-cyanoacetamide