Synthesis of highly substituted oxazoles through iodine(III)-mediated reactions of ketones with nitriles

Molecules. 2012 Sep 13;17(9):11046-55. doi: 10.3390/molecules170911046.

Abstract

In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane-sulfonyl)imide (Tf₂NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic*
  • Hydrocarbons, Fluorinated / chemistry
  • Imides / chemistry
  • Iodine / chemistry*
  • Iodobenzenes / chemistry
  • Ketones / chemistry*
  • Mesylates / chemistry
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry*

Substances

  • Hydrocarbons, Fluorinated
  • Imides
  • Iodobenzenes
  • Ketones
  • Mesylates
  • Nitriles
  • Oxazoles
  • bis(trifluoromethanesulfonyl)imide
  • Iodine
  • trifluoromethanesulfonic acid
  • iodosobenzene