Consecutive Cycloaddition/S(N)Ar/Reduction/Cyclization/Oxidation Sequences: A Copper-Catalyzed Multicomponent Synthesis of Fused N-Heterocycles

Org Lett. 2015 Jun 5;17(11):2820-3. doi: 10.1021/acs.orglett.5b01242. Epub 2015 May 21.

Abstract

A highly efficient multicomponent domino protocol has been developed for the synthesis of 5-phenyl-[1,2,3]triazolo[1,5-c]quinazolines from simple and readily available (E)-1-bromo-2-(2-nitrovinyl)benzenes, aldehydes, and sodium azide. This elegant domino process involved consecutive [3 + 2] cycloaddition, copper-catalyzed S(N)Ar, reduction, cyclization, and oxidation sequences. Notably, sodium azide acted as a dual nitrogen source in the construction of this novel fused N-heterocycle.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Copper / chemistry*
  • Cycloaddition Reaction
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry

Substances

  • Azides
  • Heterocyclic Compounds
  • Quinazolines
  • Copper