Synthesis of [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones through copper-catalyzed tandem reactions of N-(2-haloaryl)propiolamides with sodium azide

Org Lett. 2012 Mar 2;14(5):1262-5. doi: 10.1021/ol300114w. Epub 2012 Feb 15.

Abstract

A simple and efficient approach for the synthesis of [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones is described. The methodology is based on a tandem reaction of 1-(2-haloaryl)propiolamides with sodium azide through a [3 + 2] azide-alkyne cycloaddition and intramolecular Ullmann-type C-N coupling process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Molecular Structure
  • Quinoxalines / chemistry*
  • Sodium Azide / chemistry*
  • Triazoles / chemical synthesis*

Substances

  • Amides
  • Quinoxalines
  • Triazoles
  • Copper
  • Sodium Azide