Synthesis of 3-aminoisoxazoles via the addition-elimination of amines on 3-bromoisoxazolines

Org Lett. 2009 Mar 5;11(5):1159-62. doi: 10.1021/ol9000284.

Abstract

A novel two-step procedure for the synthesis of 3-amino-5-substituted-isoxazoles is described. In the presence of a base, readily available 3-bromoisoxazolines react with amines to afford 3-aminoisoxazolines. An oxidation protocol was developed for these heterocycles to provide 3-aminoisoxazoles in consistently high yield.

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Brominated / chemistry*
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Amines
  • Hydrocarbons, Brominated
  • Isoxazoles