One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes

Org Biomol Chem. 2015 Sep 14;13(34):8993-5. doi: 10.1039/c5ob01462j. Epub 2015 Aug 5.

Abstract

A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor-acceptor cyclopropanes and subsequent in situ reduction of enamine (imine) intermediates.

Publication types

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

MeSH terms

  • Amides / chemical synthesis*
  • Amines / chemistry*
  • Cyclopropanes / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • gamma-Aminobutyric Acid / chemistry*

Substances

  • Amides
  • Amines
  • Cyclopropanes
  • gamma-Aminobutyric Acid
  • cyclopropene