Synthesis of C3-substituted 4-azaindoles: an easy access to 4-azamelatonin and protected 4-azatryptophan

J Org Chem. 2008 Sep 19;73(18):7390-3. doi: 10.1021/jo8011623. Epub 2008 Aug 26.

Abstract

C3-Substituted-4-azaindoles were synthesized from pyridylacetonitriles in a two-step sequence allowing the easy introduction of a range of substituents. This strategy permits the rapid synthesis of 4-azamelatonin and a protected 4-azatryptophan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Melatonin / analogs & derivatives*
  • Melatonin / chemical synthesis
  • Melatonin / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Tryptophan / analogs & derivatives*
  • Tryptophan / chemical synthesis
  • Tryptophan / chemistry

Substances

  • 4-azaindole
  • 4-azamelatonin
  • 4-azatryptophan
  • Indoles
  • Tryptophan
  • Melatonin