Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes

Org Biomol Chem. 2012 Dec 14;10(46):9204-13. doi: 10.1039/c2ob26267c. Epub 2012 Oct 23.

Abstract

The dipolar cycloadditions of ortho-nitrophenyl alkynes with aryl nitrile oxides has been demonstrated. A range of substituents are tolerated on the alkyne. These reactions proceed with excellent levels of regioselectivity. Subsequent functionalization of the isoxazole scaffold has been demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Amides / chemical synthesis*
  • Catalysis
  • Cycloaddition Reaction
  • Isoxazoles / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Nitriles / chemistry*
  • Oxides / chemistry*
  • Oximes / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkynes
  • Amides
  • Isoxazoles
  • Nitriles
  • Oxides
  • Oximes