One step regioselective synthesis of 5-aminoisoxazoles from nitrile oxides and alpha-cyanoenamines

Molecules. 2004 Jun 30;9(7):527-34. doi: 10.3390/90700527.

Abstract

The 1,3-dipolar cycloaddition of nitrile oxides to 1-cyanoenamines gives 5-aminoisoxazoles regioselectively. Moderate to good yields could be obtained depending on the method used to generate the nitrile oxides. The intermediate isoxazolines could not be isolated.

MeSH terms

  • Acrylonitrile / analogs & derivatives*
  • Acrylonitrile / chemistry
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Oxides / chemistry*
  • Stereoisomerism

Substances

  • Isoxazoles
  • Oxides
  • Acrylonitrile