Domino Heck-aza-Michael reactions: efficient access to 1-substituted tetrahydro-beta-carbolines

J Org Chem. 2010 Mar 5;75(5):1787-90. doi: 10.1021/jo902652h.

Abstract

A simple and efficient palladium-catalyzed domino reaction for the synthesis of a series of C1-substituted tetrahydro-beta-carbolines is described. This domino process involves a Heck reaction at the indole 2-position of a halogenated tryptamine precursor, followed by intramolecular aza-Michael addition.

MeSH terms

  • Aza Compounds / chemistry*
  • Carbolines / chemical synthesis*
  • Carbolines / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Palladium / chemistry
  • Stereoisomerism
  • Tryptamines / chemistry*

Substances

  • Aza Compounds
  • Carbolines
  • Tryptamines
  • Palladium