InBr3-mediated one-pot synthesis of 2-(polyhydroxylatedalkyl)-N-aryl-/-alkylpyrroles from 1,2-cyclopropa-3-pyranone and amines

Org Lett. 2013 Aug 2;15(15):3852-5. doi: 10.1021/ol401489x. Epub 2013 Jul 15.

Abstract

An efficient one-pot synthesis of polyhydroxyalkyl-substituted pyrroles from 1,2-cyclopropa-3-pyranones with primary amines is reported. With 10% of InBr3 as the catalyst, both aryl- and alkylamines as well as various 1,2-cyclopropa-3-pyranones are well tolerated. This method is highly appealing because of its one-pot process, mild reaction conditions, substrate simplicity, and broad substrate scope.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Indium / chemistry*
  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*

Substances

  • Amines
  • Pyrones
  • Pyrroles
  • indium bromide
  • Indium