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Synthesis of 2-arylidene-6,7-dihydroimidazo[1,2-a]pyrazine-3,8(2H,5H)-diones by 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

(Z)-4-Arylidene-2-methyl-1H-imidazol-5(4H)-ones containing a substituted aminoethyl group at the N-1 atom can be oxidized with an excess of selenium dioxide, resulting in the closure of additional six-membered ring with the formation of an amide group. The obtained compounds showed a substantial bathochromic shift of the absorption maxima relative to the starting (Z)-4-arylidene-2-methyl-1Himidazol-5(4H)-ones, pointing to potential applications of this method for the synthesis of new fluorescent and fluorogenic dyes.

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This study received financial support from the grant MK-189.2017.3 of the President of the Russian Federation. Experiments were partially carried out using the equipment provided by the IBCH core facility (CKP IBCH, supported by the Russiian Ministry of Education and Science, grant RFMEFI62117X0018).

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry named after Academicians М. М. Shemyakin and Yu. A. Ovchinnikov, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St, Moscow, 117997, GSP-7, Russia

    Nadezhda S. Baleeva, Evgeniya A. Levina & Mikhail S. Baranov

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  1. Nadezhda S. Baleeva
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  2. Evgeniya A. Levina
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  3. Mikhail S. Baranov
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Correspondence to Nadezhda S. Baleeva.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 930–933

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Baleeva, N.S., Levina, E.A. & Baranov, M.S. Synthesis of 2-arylidene-6,7-dihydroimidazo[1,2-a]pyrazine-3,8(2H,5H)-diones by oxidation of 4-arylidene-2-methyl-1H-imidazol-5(4H)-ones with selenium dioxide. Chem Heterocycl Comp 53, 930–933 (2017). https://doi.org/10.1007/s10593-017-2149-y

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  • DOI: https://doi.org/10.1007/s10593-017-2149-y

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