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Russian Chemical Bulletin

, Volume 68, Issue 1, pp 191–193 | Cite as

An unusual reduction of azido group accompanied by ring closure to 1,2,3-triazole 3-oxide

  • A. A. Konnov
  • M. S. Klenov
  • A. M. ChurakovEmail author
  • Yu. A. Strelenko
  • I. V. FedyaninEmail author
  • V. A. Tartakovsky
Brief Communications
  • 11 Downloads

Abstract

The reaction of 2-[(2-azidophenyl)hydrazono]-2-(tert-butyl-NNO-azoxy)-N′-hydr oxyethanimidamide with sodium acetate in DMF aff ords 2-(2-aminophenyl)-5-(tert-butyl-NNO-azoxy)-2H-1,2,3-triazol-4-amine 3-oxide rather than the anticipated 2-(2-azidophenyl)-5- (tert-butyl-NNO-azoxy)-2H-1,2,3-triazol-4-amine. The formation of this product can be explained by intramolecular reduction of azido to amino group and cyclization of an inter mediate vicinal (azo)nitrosoethylene into a triazole 3-oxide ring. The structure of aminotriazole 3-oxide 10 was confirmed by X-ray diff raction and NMR spectroscopy.

Key words

1,2,3-triazoles azides reduction cyclization X-ray diff raction 

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Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • A. A. Konnov
    • 1
  • M. S. Klenov
    • 1
  • A. M. Churakov
    • 1
    Email author
  • Yu. A. Strelenko
    • 1
  • I. V. Fedyanin
    • 2
    Email author
  • V. A. Tartakovsky
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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