Cu(II)-catalyzed domino reaction of 2H-azirines with diazotetramic and diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles

Org Biomol Chem. 2013 Sep 7;11(33):5535-45. doi: 10.1039/c3ob40708j.

Abstract

The Cu(II)-catalyzed addition of two molecules of a 3-aryl-2H-azirine to diazotetramic or diazotetronic acids proceeds as a domino reaction with the formation of 1,2,3-triazole derivatives with ortho-fused (pyrrolo[3,4-b]pyrrol or furo[3,4-b]pyrrol) and spiro-cyclic (1-oxa-4,7-diazaspiro[4.4]nonane or 1,7-dioxa-4-azaspiro[4.4]nonane) substituents at the N2 position. The disclosed reaction is a new type of formation of a 1,2,3-triazole ring from (N-N) and (C-C-N) building blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azirines / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry
  • Copper / chemistry*
  • Molecular Structure
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Azirines
  • Azo Compounds
  • Coordination Complexes
  • Triazoles
  • Copper