Copper-catalyzed domino cycloaddition/C-N coupling/cyclization/(C-H arylation): an efficient three-component synthesis of nitrogen polyheterocycles

Angew Chem Int Ed Engl. 2013 Oct 11;52(42):10992-6. doi: 10.1002/anie.201305970. Epub 2013 Sep 6.

Abstract

A cat of all trades: A single copper catalyst promoted up to three reaction steps with separate catalytic cycles in a domino sequence (azide-alkyne cycloaddition/Goldberg amidation/Camps cyclization/(CH arylation)) for the rapid construction of complex heterocycles from three simple components under mild conditions. Facile cleavage of the triazole ring enables further elaboration of the condensation products.

Keywords: CH arylation; amidation; copper catalysis; heterocycles; multicomponent reactions.

MeSH terms

  • Copper / chemistry*
  • Cyclization
  • Cycloaddition Reaction / methods*
  • Heterocyclic Compounds / chemical synthesis*
  • Molecular Structure
  • Nitrogen / chemistry*

Substances

  • Heterocyclic Compounds
  • Copper
  • Nitrogen