Metal-free synthesis of 3,3-disubstituted oxoindoles by iodine(III)-catalyzed bromocarbocyclizations

Chemistry. 2012 Aug 27;18(35):10834-8. doi: 10.1002/chem.201201232. Epub 2012 Jul 11.

Abstract

"I" did it: An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio- and stereoselective fashion. The indole-2-ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemistry
  • Bromides / chemistry
  • Bromosuccinimide / chemistry*
  • Catalysis
  • Cyclization
  • Halogenation
  • Indoles / chemical synthesis*
  • Molecular Structure
  • Physostigmine / chemical synthesis*
  • Potassium Compounds / chemistry

Substances

  • Acrylamides
  • Bromides
  • Indoles
  • Potassium Compounds
  • Physostigmine
  • methacrylamide
  • Bromosuccinimide
  • potassium bromide