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Unusual nicotinoylation of 4-phenyl-5,7-dihydroxycoumarin

A. D. Sharapov, R. F. Fatykhov, I. A. Khalymbadzha, A. P. Potapova, P. A. Slepukhin, O. N. Chupakhin


In the present work, we report a convenient synthesis of 5- and 7-substituted-4-phenyl coumarins. In contrast to previous results obtained with 4-alkylcoumarins, nicotinoylation of 5,7-dihydroxy-4-phenylcoumarin with nicotinoyl benzotriazole or nicotinoyl azide selectively provides 5-O protected ester. The combination of the nicotinoylation reaction followed by tosylation-denicotinoylation yields 5-hydroxy-7-tosyloxy-coumarin derivative, which may be useful in the synthesis of inophyllum, a tetracyclic HIV reverse transcriptase inhibitor, as well as its analogues.


5,7-dihydroxy-4-phenylcoumarin; nicotinoylation; esterification; protecting group; inophyllum

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Copyright (c) 2021 A.D. Sharapov, R.F. Fatykhov, I.A. Khalymbadzha, A.P. Potapova, P.A. Slepukhin, O.N. Chupakhin

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Chimica Techno Acta, 2014-2023
ISSN 2411-1414 (Online)
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