Open AccessUnusual nicotinoylation of 4-phenyl-5,7-dihydroxycoumarin
Author(s) -
Ainur D. Sharapov,
Ramil F. Fatykhov,
Igor A. Khalymbadzha,
Anastasya P. Potapova,
П. А. Слепухин,
О. Н. Чупахин
Publication year - 2022
Publication title -
chimica techno acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.128
H-Index - 1
eISSN - 2411-1414
pISSN - 2409-5613
DOI - 10.15826/chimtech.2022.9.1.05
Subject(s) - benzotriazole , coumarin , derivative (finance) , chemistry , azide , combinatorial chemistry , stereochemistry , organic chemistry , economics , financial economics
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.