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Russian Chemical Bulletin

, Volume 58, Issue 1, pp 191–202 | Cite as

Fused polycyclic nitrogen-containing heterocycles 20. Thiazolo[3,4-a]quinoxalines from 4-hydroxy-2-phenyliminothiazolidines and C-substituted 1,2-phenylenediamines

  • V. A. Mamedov
  • N. A. Zhukova
  • T. N. Beschastnova
  • A. T. Gubaidullin
  • Ya. A. Levin
  • I. A. Litvinov
Full Articles

Abstract

The condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 4,5-dimethyl-1,2-phenylenediamine affords 7,8-dimethyl-3-phenyl-1-phenyliminothiazolo[3,4-a]quinox-alin-4(5 H)- one; the condensation with 1,2-phenylenediamines containing different substituents at positions 4 and 5 gives both theoretically possible isomeric thiazolo[3,4-a]quinoxalines, which differ in the distribution of these substituents between positions 7 and 8 in the benzene ring of the quinoxaline system. 3a-Hydroxy-7,8-dimethyl-3-phenyl-l-phenylimino-3,3a-di-hydrothiazolo[3,4-a]quinoxalin4(5 H)- one was isolated and characterized as the intermediate of the reaction giving rise to thiazolo[3,4-a]quinoxaline from 4,5-dimethyl-1,2-phenylene-diamine. This intermediate is a covalent hydrate of the final product.

Key words

Hantzsch reaction 4-hydroxythiazoklidines thiazolo[3,4-a]quinoxalines IR spectroscopy NMR spectroscopy X-ray diffraction study 

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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • V. A. Mamedov
    • 1
  • N. A. Zhukova
    • 1
  • T. N. Beschastnova
    • 1
  • A. T. Gubaidullin
    • 1
  • Ya. A. Levin
    • 1
  • I. A. Litvinov
    • 1
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Research Center of the Russian Academy of SciencesKazanRussian Federation

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