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.

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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