A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles

Chem Commun (Camb). 2009 Jan 7:(1):104-6. doi: 10.1039/b816989f. Epub 2008 Nov 11.

Abstract

The key steps of a versatile new protocol for the convergent synthesis of 3,4-disubstituted indoles are the addition of an alpha-lithiated alkylaminofuran to a carbonyl compound, a microwave-accelerated intramolecular Diels-Alder cycloaddition and an in situ double aromatization reaction.

Publication types

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

MeSH terms

  • Cyclization
  • Electrons
  • Furans / chemistry*
  • Heterocyclic Compounds / chemistry
  • Indicators and Reagents
  • Indoles / chemical synthesis*
  • Indoles / radiation effects
  • Lithium / chemistry
  • Microwaves

Substances

  • Furans
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Indoles
  • Lithium