Efficient regioselective synthesis of indole N-carboximidamides and N-carboximidoates by a sequential Aza-Wittig/Ag(I)-catalyzed cyclization

J Org Chem. 2009 Sep 4;74(17):6874-7. doi: 10.1021/jo901362c.

Abstract

An efficient Ag(I)-catalyzed regioselective cyclization of (2-alkynylphenyl)guanidine or (2-alkynylphenyl)isourea to indole N-carboximidamides or N-carboximidoates has been developed. The approach has the advantages of high regioselectivity, mild reaction conditions, easily accessible starting materials, and good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Chemistry, Organic / methods
  • Chemistry, Pharmaceutical / methods
  • Crystallography, X-Ray
  • Cyclization
  • Drug Design
  • Imides / chemical synthesis*
  • Imides / chemistry
  • Indoles / chemical synthesis*
  • Models, Chemical
  • Molecular Structure
  • Silver / chemistry
  • Temperature
  • Urea / chemistry

Substances

  • Amides
  • Imides
  • Indoles
  • Silver
  • Carbon
  • Urea