Unconventional oxazole formation from isocyanides

Chem Commun (Camb). 2009 Jul 14:(26):3907-9. doi: 10.1039/b904699b. Epub 2009 May 20.

Abstract

The coupling of an acyl chloride with an isocyanide affords 2,5-disubstituted oxazoles under mild basic conditions instead of 4,5-disubstituted derivatives when using Schöllkopf conditions (butyllithium); this reaction constitutes a remarkable example of a base-induced chemoselective process in isocyanide chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyanides / metabolism*
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Oxazoles / metabolism*

Substances

  • Cyanides
  • Oxazoles