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Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction

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Abstract

The effect of electronic properties of substituents in the reactants on the [4+2]-cycloaddition of 3-vinyl-chromen-4-ones (dienes) and N-vinylpyrrolidines (dienophiles) has been studied. The conditions determining the formation of 4,4a-dihydroxanthones or benzophenones as the major products have been found. The aromatization of 4,4a-dihydroxanthones via pyran ring opening has been interpreted by quantum chemical calculations. A wide series of new 4,4a-dihydroxanthone and benzophenone derivatives have been isolated.

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Funding

This study was financially supported by the scholarship from the Council for Grants at the President of the Russian Federation (competition SP-2019).

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Authors and Affiliations

  1. St. Petersburg State Chemical Pharmaceutical University, St. Petersburg, 197376, Russia

    N. M. Chernov, T. V. Moroz, R. V. Shutov, A. E. Shchegolev, M. V. Sopova & I. P. Yakovlev

  2. Institute for Translational Medicine and Biotechnology, Sechenov First Moscow State Medical University, Moscow, 119146, Russia

    N. N. Kuz’mich

  3. Smorodintsev Research Institute of Influenza, St. Petersburg, 197376, Russia

    N. N. Kuz’mich

Authors
  1. N. M. Chernov
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  2. T. V. Moroz
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  3. R. V. Shutov
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  4. N. N. Kuz’mich
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  5. A. E. Shchegolev
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  6. M. V. Sopova
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  7. I. P. Yakovlev
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Correspondence to N. M. Chernov.

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Chernov, N.M., Moroz, T.V., Shutov, R.V. et al. Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction. Russ J Gen Chem 89, 2463–2470 (2019). https://doi.org/10.1134/S1070363219120223

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  • DOI: https://doi.org/10.1134/S1070363219120223

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