Modular one-pot synthesis of tetrasubstituted pyrroles from alpha-(alkylideneamino)nitriles

J Org Chem. 2007 Sep 14;72(19):7083-90. doi: 10.1021/jo070426x. Epub 2007 Aug 22.

Abstract

2,3,4,5-Tetrasubstituted pyrroles have been prepared with high regioselectivity by a formal cycloaddition of alpha-(alkylideneamino)nitriles and nitroolefins followed by elimination of HCN and HNO2. The reaction allows the convergent construction of the pyrrole ring in four steps from a nitroalkane and three aldehydes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Cyclization
  • Nitriles / chemistry*
  • Nitro Compounds / chemistry
  • Pyrroles / chemical synthesis*

Substances

  • Aldehydes
  • Alkenes
  • Nitriles
  • Nitro Compounds
  • Pyrroles