Chemistry of Heterocyclic Compounds

, Volume 49, Issue 7, pp 1024–1032 | Cite as

Synthesis of pyrrolo[1,2-a][1,6]benzodiazonines from pyrrolo[1,2-a][1,4]benzodiazepines and alkynes containing electron-acceptor substituents

  • L. G. Voskressensky
  • T. N. Borisova
  • M. I. Babakhanova
  • T. M. Chervyakova
  • A. A. Titov
  • A. V. Butin
  • T. A. Nevolina
  • V. N. Khrustalev
  • A. V. Varlamov
Article
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Revised:

It has been established that the reaction of pyrrolo[1,2-a][1,4]benzodiazepines with activated alkynes gives pyrrolo[1,2-a][1,6]benzodiazonines as the products of diazepine ring expansion. In the case of pyrrolo[1,2-a][1,4]benzodiazepine, substituted with formyl group at the pyrrole ring, both expansion and cleavage of the diazepine fragment can occur.

Keywords

pyrrolo[1,2-a][1,4]benzodiazepines pyrrolo[1,2-a][1,6]benzodiazonines activated alkynes diazepine ring expansion diazepine ring opening 
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Notes

This work was carried out within the scope of the Presidential grant in support of young Russian scientists (MK-182.2012.3). The authors thank the Collective Use Center of the Peoples’ Friendship University of Russia for help with recording the 1H NMR spectra.

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • L. G. Voskressensky
    • 1
  • T. N. Borisova
    • 1
  • M. I. Babakhanova
    • 1
  • T. M. Chervyakova
    • 1
  • A. A. Titov
    • 1
  • A. V. Butin
    • 2
    • 3
  • T. A. Nevolina
    • 2
    • 3
  • V. N. Khrustalev
    • 4
  • A. V. Varlamov
    • 1
  1. 1.Peoples’ Friendship University of RussiaMoscowRussia
  2. 2.Research Institute for Heterocyclic CompoundsKuban State University of TechnologyKrasnodarRussia
  3. 3.Perm State National Research UniversityPermRussia
  4. 4.A. N. Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of SciencesMoscowRussia

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