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Synthesis of aurone derivatives on the basis of 2,4,6-trihydroxytoluene

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Chemistry of Heterocyclic Compounds Aims and scope

2,4,6-Trihydroxytoluene (2-methylphloroglucinol) was used as starting material for the first synthesis of several (Z)-2-arylidene-4,6-dihydroxy-7-methylaurones, including a synthetic analog of the natural 7-methylaureusidin, which is currently obtained mainly from the extract of sedge capitata (Cyperus capitatus). It was shown that the reaction of 2,4,6-trihydroxytoluene with chloroacetonitrile occurred regioselectively, with the formation of 4,6-dihydroxy-7-methylbenzofuran-3(2H)-one, the treatment of which with substituted benzaldehydes gave high yields of the target compounds.

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Authors and Affiliations

  1. Russian State University named after A. N. Kosygin (Technology. Design. Art), 1 Malaya Kaluzhskaya St., Moscow, 119991, Russia

    Dmitry A. Shubin, Dmitry N. Kuznetsov & Konstantin I. Kobrakov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Alexey M. Starosotnikov & Natal’ya L. Merkulova

Authors
  1. Dmitry A. Shubin
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  2. Dmitry N. Kuznetsov
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  3. Konstantin I. Kobrakov
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  4. Alexey M. Starosotnikov
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  5. Natal’ya L. Merkulova
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Correspondence to Dmitry N. Kuznetsov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(12), 1174–1178

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Shubin, D.A., Kuznetsov, D.N., Kobrakov, K.I. et al. Synthesis of aurone derivatives on the basis of 2,4,6-trihydroxytoluene. Chem Heterocycl Comp 55, 1174–1178 (2019). https://doi.org/10.1007/s10593-019-02597-0

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  • DOI: https://doi.org/10.1007/s10593-019-02597-0

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