Chemistry of Heterocyclic Compounds

, Volume 53, Issue 5, pp 575–581 | Cite as

Synthesis of 1-tetrazolyl-substituted 2,3,4,9-tetrahydro-1H-β-carbolines and their transformations involving activated alkynes

  • Leonid G. Vosskresensky
  • Alexander A. Titov
  • Reza Samavati
  • Maxim S. Kobzev
  • Pavel V. Dorovatovskii
  • Victor N. Khrustalev
  • Hieu Chuong Hong
  • Tuet An Dang Thi
  • Tuyen Nguyen Van
  • Elena A. Sorokina
  • Alexey V. Varlamov
Article
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1-Tetrazolyl-substituted tetrahydro-β-carbolines undergo a reaction with activated alkynes (acetylacetylene, methyl propiolate, and dimethyl acetylenedicarboxylate) over 4–8 days in MeOH or 1 day in CF3CH2OH with the formation of multicomponent mixtures, from which spiro[indole-3,4'-pyridines] were isolated chromatographically. Additionally, two azocino[5,4-b]indoles were isolated from methyl propiolate and acetylacetylene reactions.

Keywords

acetylacetylene azocinoindoles dimethyl acetylenedicarboxylate methyl propiolate spiro[indole-3,4'-pyridines] tetrazolylsubstituted tetrahydro-β-carbolines 

Notes

The publication was financially supported by the Ministry of Education and Science of the Russian Federation (Agreement № 02.A03.21.0008), the Russian Foundation for Basic Research (grants 15-33-20187, 16-53-540004, 17-53-540001), and Vietnam (VAST.HTQT.NGA.06/16-17).

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Leonid G. Vosskresensky
    • 1
  • Alexander A. Titov
    • 1
  • Reza Samavati
    • 1
  • Maxim S. Kobzev
    • 1
  • Pavel V. Dorovatovskii
    • 2
  • Victor N. Khrustalev
    • 1
    • 3
  • Hieu Chuong Hong
    • 4
  • Tuet An Dang Thi
    • 4
  • Tuyen Nguyen Van
    • 4
  • Elena A. Sorokina
    • 1
  • Alexey V. Varlamov
    • 1
  1. 1.Peoples’ Friendship University of RussiaMoscowRussia
  2. 2.National Research Center “Kurchatov Institute”MoscowRussia
  3. 3.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  4. 4.Institute of Chemistry of Vietnam Academy of Science and TechnologyHanoiVietnam

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