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Synthesis of 2-arylideneimidazo[1,2-a]pyrazine-3,6,8(2H,5H,7H)-triones as a result of oxidation of 4-arylidene-2-methyl-1H-imidazol-5(4H)-ones with selenium dioxide

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Chemistry of Heterocyclic Compounds Aims and scope

4-Arylidene-2-methyl-1H-imidazol-5(4H)-ones with an acetamide substituent at position 1 of the imidazolone ring can be oxidized with selenium dioxide to form a six-membered imide ring. The spectra of the obtained 2-arylideneimidazo[1,2-a]pyrazine-3,6,8(2H,5H,7H)-triones exhibit significant bathochromic shifts of the absorption and emission maxima in comparison with the spectra of the starting imdazolones, which suggests that the synthesized compounds could be used as fluorogenic dyes.

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Authors and Affiliations

  1. D. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

    Elvira R. Zaitseva

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

    Elvira R. Zaitseva, Alexander Yu. Smirnov, Ivan N. Myasnyanko, Anatolii I. Sokolov & Mikhail S. Baranov

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

    Mikhail S. Baranov

Authors
  1. Elvira R. Zaitseva
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  2. Alexander Yu. Smirnov
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  3. Ivan N. Myasnyanko
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  4. Anatolii I. Sokolov
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  5. Mikhail S. Baranov
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Correspondence to Alexander Yu. Smirnov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 116–119

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Zaitseva, E.R., Smirnov, A.Y., Myasnyanko, I.N. et al. Synthesis of 2-arylideneimidazo[1,2-a]pyrazine-3,6,8(2H,5H,7H)-triones as a result of oxidation of 4-arylidene-2-methyl-1H-imidazol-5(4H)-ones with selenium dioxide. Chem Heterocycl Comp 56, 116–119 (2020). https://doi.org/10.1007/s10593-020-02634-3

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  • DOI: https://doi.org/10.1007/s10593-020-02634-3

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