Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction
- Authors: Chernov N.M.1, Moroz T.V.1, Shutov R.V.1, Kuz’mich N.N.2,3, Shchegolev A.E.1, Sopova M.V.1, Yakovlev I.P.1
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Affiliations:
- St. Petersburg State Chemical Pharmaceutical University
- Institute for Translational Medicine and Biotechnology
- Smorodintsev Research Institute of Influenza
- Issue: Vol 89, No 12 (2019)
- Pages: 2463-2470
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/223215
- DOI: https://doi.org/10.1134/S1070363219120223
- ID: 223215
Cite item
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.
About the authors
N. M. Chernov
St. Petersburg State Chemical Pharmaceutical University
Author for correspondence.
Email: nikita.chernov@pharminnotech.com
Russian Federation, St. Petersburg, 197376
T. V. Moroz
St. Petersburg State Chemical Pharmaceutical University
Email: nikita.chernov@pharminnotech.com
Russian Federation, St. Petersburg, 197376
R. V. Shutov
St. Petersburg State Chemical Pharmaceutical University
Email: nikita.chernov@pharminnotech.com
Russian Federation, St. Petersburg, 197376
N. N. Kuz’mich
Institute for Translational Medicine and Biotechnology; Smorodintsev Research Institute of Influenza
Email: nikita.chernov@pharminnotech.com
Russian Federation, Moscow, 119146; St. Petersburg, 197376
A. E. Shchegolev
St. Petersburg State Chemical Pharmaceutical University
Email: nikita.chernov@pharminnotech.com
Russian Federation, St. Petersburg, 197376
M. V. Sopova
St. Petersburg State Chemical Pharmaceutical University
Email: nikita.chernov@pharminnotech.com
Russian Federation, St. Petersburg, 197376
I. P. Yakovlev
St. Petersburg State Chemical Pharmaceutical University
Email: nikita.chernov@pharminnotech.com
Russian Federation, St. Petersburg, 197376
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