Chemistry of Heterocyclic Compounds

, Volume 55, Issue 9, pp 882–887 | Cite as

Thermolysis of 3-azido-4-aryl(hetaryl)thieno[2,3-b]pyridines: 2,7-naphthyridines or 1,4-diazepines?

  • Eugeniya А. KanishchevaEmail author
  • Veronika O. Bedareva
  • Vladimir K. Vasilin
  • Tat’yana А. Stroganova
  • Gennady D. Krapivin

A series of tertiary 3-azido-N-phenylthieno[2,3-b]pyridine-2-carboxamides containing a phenyl or hetaryl moiety at position 4 were synthesized. The influence of the nature of the substituent on the direction of intramolecular cyclization with the participation of nitrene was studied. Novel pyrido[3',2':4,5]thieno[3,2-b][1,5]benzodiazepin-11-ones and benzo[c]thieno[2,3,4-ij][2,7]naphthyridines were synthesized.


3-aminothieno[2,3-b]pyridines annulated 2,7-naphthyridines azides 1,4-diazepines heterocyclization thermolysis 


This work was financially supported by the Ministry of Education and Science of the Russian Federation (agreement 4.6087.2017/BCh) and the Russian Foundation for Basic Research (agreement No. 18-33-00184/18).


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Eugeniya А. Kanishcheva
    • 1
    Email author
  • Veronika O. Bedareva
    • 1
  • Vladimir K. Vasilin
    • 1
  • Tat’yana А. Stroganova
    • 1
  • Gennady D. Krapivin
    • 1
  1. 1.Kuban State Technological UniversityKrasnodarRussia

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