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Russian Chemical Bulletin

, Volume 68, Issue 8, pp 1504–1509 | Cite as

Reactions of donor-acceptor cyclopropanes or benzylidenemalonate with benzyl azide by generating gallium trichloride 1,2-zwitterionic complexes

  • I. A. Borisova
  • A. V. Tarasova
  • K. V. Potapov
  • R. A. Novikov
  • Yu. V. TomilovEmail author
Full Article
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Abstract

The reactions of 1,2-zwitterionic complexes, generated from 2-arylcyclopropane-1,1-dicarboxylates (ACDC) or benzylidenemalonate and gallium trichloride, with benzyl azide proceeds as a formal [3+2] cycloaddition to form dihydro-1,2,3-triazoles. The latter, when the reaction mixture is treated with 10% aqueous HCl, undergo retrocyclization with elimination of diazomalonate. The reaction of ACDC, benzyl azide, and GaCl3 with simultaneous mixing of the reagents leads to the interception of the 1,3-zwitterion, with this stage being accompanied by both the cyclization to substituted 1,2,3-triazinine and the elimination of a nitrogen molecule to form 3,4-dihydro-2H-1,2-oxazine structure, which after acid hydrolysis gives substituted 3-hydroxypyrrolidin-2-one.

Key words

donor-acceptor cyclopropanes 1,2-zwitterionic complexes gallium trichloride benzyl azide N-heterocyclic compounds 

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Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • I. A. Borisova
    • 1
  • A. V. Tarasova
    • 1
  • K. V. Potapov
    • 1
  • R. A. Novikov
    • 1
  • Yu. V. Tomilov
    • 1
    Email author
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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