Cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: the amide question

Molecules. 2011 Aug 25;16(9):7267-87. doi: 10.3390/molecules16097267.

Abstract

The n-butyramido, isobutyramido, benzamido, and furancarboxamido functions profoundly modulate the electronics of the stilbene olefinic and NH groups and the corresponding radical cations in ways that influence the efficiency of the cyclization due presumably to conformational and stereoelectronic factors. For example, isobutyramido- stilbene undergoes FeCl(3) promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Cations
  • Chlorides / chemistry
  • Cyclization
  • Dimerization
  • Ferric Compounds / chemistry
  • Free Radicals / chemistry
  • Indoles / chemical synthesis
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism
  • Stilbenes / chemistry*

Substances

  • Amides
  • Cations
  • Chlorides
  • Ferric Compounds
  • Free Radicals
  • Indoles
  • Stilbenes
  • indoline
  • ferric chloride