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Unusual nicotinoylation of 4-phenyl-5,7-dihydroxycoumarin
Abstract
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.
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DOI: https://doi.org/10.15826/chimtech.2022.9.1.05
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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