An efficient entry to 1,2-benzisoxazoles via 1,3-dipolar cycloaddition of in situ generated nitrile oxides and benzyne

Org Biomol Chem. 2010 Jun 7;8(11):2537-42. doi: 10.1039/b927235f. Epub 2010 Apr 7.

Abstract

An efficient protocol for the synthesis of a range of 1,2-benzisoxazoles using an improved 1,3-dipolar cycloaddition of nitrile oxides and benzyne is described. Key to the procedure is the in situ generation of the reactive nitrile oxide and benzyne reactants simultaneously.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Cyclization
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxides / chemistry*
  • ortho-Aminobenzoates / chemistry

Substances

  • 1,2-benzisoxazole
  • Benzene Derivatives
  • Isoxazoles
  • Nitriles
  • Oxides
  • benzyne
  • ortho-Aminobenzoates
  • anthranilic acid