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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1785–1794 | Cite as

Transformation of 4-Substituted Tetrahydro-Pyrrolobenzodiazepines in a Three-Component Reaction With Methyl Propiolate and Indole

  • L. G. VoskressenskyEmail author
  • T. N. Borisova
  • M. I. Babakhanova
  • A. A. Titov
  • T. M. Chervyakova
  • R. A. Novikov
  • A. V. Butin
  • V. N. Khrustalev
  • A. V. Varlamov
Article

The three-component reaction of 4-phenyl-, p-methoxyphenyl-, and thienylpyrrolo[1,2-a][1,4]benzo-diazepines with methyl propiolate and indole in dichloromethane proceeds through opening of the diazepine ring. The major transformation products isolated are substituted pyrroles, namely, 1-(2-aminomethylphenyl)-5-(arylmethyl)-2-(indol-1(3)-yl)pyrroles and 1-(2-aminomethylphenyl)-2-aryl-(indol-3-yl)-methylpyrroles.

Keywords

pyrrolylindoles tetrahydropyrrolo[1,2-a][1,4]benzodiazepines domino reactions multi-component reaction opening of the diazepine ring 

Notes

This work was carried out with the support of the Russian Foundation for Basic Research (grants 11-03-00164 and 13-03-09431 Ukrfa) and the Grants Council of the President of the Russian Federation (grant MK-182.2012.03).

The authors express their gratitude to Shared Research and Educational Center of the People’s Friendship University of Russia (SREC PFUR) for taking the 1H NMR spectra.

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • L. G. Voskressensky
    • 1
    Email author
  • T. N. Borisova
    • 1
  • M. I. Babakhanova
    • 1
  • A. A. Titov
    • 1
  • T. M. Chervyakova
    • 1
  • R. A. Novikov
    • 2
  • A. V. Butin
    • 3
  • V. N. Khrustalev
    • 4
  • A. V. Varlamov
    • 1
  1. 1.Peoples’ Friendship University of RussiaMoscowRussia
  2. 2.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of SciencesMoscowRussia
  3. 3.Perm State National Research UniversityPermRussia
  4. 4.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of SciencesMoscowRussia

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