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Synthesis of julolidine derivatives via SnCl4-promoted spirocyclization of (1-alkyltetrahydroquinolin-8-yl)methylidene-1H-imidazol-5(4H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

(1-Alkyltetrahydroquinolin-8-yl)methylidene-1H-imidazol-5(4H)-ones undergo spirocyclization by the action of SnCl4 via 1,5-hydride shift to form spirocyclic julolidine derivatives in 68–97% yields.

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This work was supported by the Russian Science Foundation (grant no. 20-73-10195).

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St, Moscow, 117997, Russia

    Vasilissa V. Shirokova, Alexander Yu. Smirnov, Elvira R. Zaitseva, Nadezhda S. Baleeva, Andrey А. Mikhaylov & Mikhail S. Baranov

  2. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq, Moscow, 125047, Russia

    Vasilissa V. Shirokova & Elvira R. Zaitseva

  3. Pirogov Russian National Research Medical University, 1 Ostrovityanova St, Moscow, 117997, Russia

    Nadezhda S. Baleeva & Mikhail S. Baranov

Authors
  1. Vasilissa V. Shirokova
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  2. Alexander Yu. Smirnov
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  3. Elvira R. Zaitseva
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  4. Nadezhda S. Baleeva
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  5. Andrey А. Mikhaylov
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  6. Mikhail S. Baranov
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Corresponding authors

Correspondence to Andrey А. Mikhaylov or Mikhail S. Baranov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 255–259

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Shirokova, V.V., Smirnov, A.Y., Zaitseva, E.R. et al. Synthesis of julolidine derivatives via SnCl4-promoted spirocyclization of (1-alkyltetrahydroquinolin-8-yl)methylidene-1H-imidazol-5(4H)-ones. Chem Heterocycl Comp 58, 255–259 (2022). https://doi.org/10.1007/s10593-022-03080-z

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  • DOI: https://doi.org/10.1007/s10593-022-03080-z

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