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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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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Authors and Affiliations

  1. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St, Moscow, 117198, Russia

    Leonid G. Vosskresensky, Alexander A. Titov, Reza Samavati, Maxim S. Kobzev, Victor N. Khrustalev, Elena A. Sorokina & Alexey V. Varlamov

  2. National Research Center “Kurchatov Institute”, 1 Akademika Kurchatova Sq, Moscow, 123182, Russia

    Pavel V. Dorovatovskii

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, Moscow, 119991, Russia

    Victor N. Khrustalev

  4. Institute of Chemistry of Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam

    Hieu Chuong Hong, Tuet An Dang Thi & Tuyen Nguyen Van

Authors
  1. Leonid G. Vosskresensky
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  2. Alexander A. Titov
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  3. Reza Samavati
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  4. Maxim S. Kobzev
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  5. Pavel V. Dorovatovskii
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  6. Victor N. Khrustalev
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  7. Hieu Chuong Hong
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  8. Tuet An Dang Thi
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  9. Tuyen Nguyen Van
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  10. Elena A. Sorokina
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  11. Alexey V. Varlamov
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Corresponding author

Correspondence to Leonid G. Vosskresensky.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 575–581

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Vosskresensky, L.G., Titov, A.A., Samavati, R. et al. Synthesis of 1-tetrazolyl-substituted 2,3,4,9-tetrahydro-1H-β-carbolines and their transformations involving activated alkynes. Chem Heterocycl Comp 53, 575–581 (2017). https://doi.org/10.1007/s10593-017-2094-9

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  • DOI: https://doi.org/10.1007/s10593-017-2094-9

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