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Issue 33, 2013
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Cu(II)-catalyzed domino reaction of 2H-azirines with diazotetramic and diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles

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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.

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

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Publication details

The article was received on 09 Apr 2013, accepted on 21 Jun 2013 and first published on 25 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40708J
Citation: Org. Biomol. Chem., 2013,11, 5535-5545
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    Cu(II)-catalyzed domino reaction of 2H-azirines with diazotetramic and diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles

    N. V. Rostovskii, M. S. Novikov, A. F. Khlebnikov, S. M. Korneev and D. S. Yufit, Org. Biomol. Chem., 2013, 11, 5535
    DOI: 10.1039/C3OB40708J

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