4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 33, Pages 5535-5545

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40708j

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Funding

  1. Russian Foundation for Basic Research [11-03-00186]
  2. Saint Petersburg State University [12.38.78.2012]

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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.

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