A Sonogashira cross-coupling/5-exo-dig cyclization/ionic hydrogenation sequence: synthesis of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones from 2-iodocyclopropanecarboxamides

J Org Chem. 2013 Jun 7;78(11):5794-9. doi: 10.1021/jo400713u. Epub 2013 May 15.

Abstract

A variety of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones have been prepared from 2-iodocyclopropanecarboxamides by a three-step sequence involving a copper-free Sonogashira coupling with terminal aryl- or heteroarylalkynes, followed by a 5-exo-dig cyclization and an ionic hydrogenation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Cyclization
  • Cyclopropanes / chemistry*
  • Hydrogenation
  • Ions / chemistry
  • Molecular Conformation

Substances

  • Alkynes
  • Bridged Bicyclo Compounds, Heterocyclic
  • Cyclopropanes
  • Ions