Synthesis of Geranyloxycoumarin Derivatives under Mild Conditions Using Cs2CO3

Authors : Sumi HWANG, Eonjoo ROH

Pages : 57-66

Doi:10.18596/jotcsa.996363

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Publication Date : 2022-02-28

Article Type : Research Paper

Abstract :In this study, the synthesis of various geranyloxycoumarin derivatives from hydroxycoumarin was obtained in good yield under mild conditions using Cs2CO3. In the synthesis of geranyloxycoumarin derivatives, when 4-hydroxycoumarin reacts with geranyl bromide under mild conditions due to tautomeric keto-enol forms, 4-geranyoxycoumarin insert ignore into journalissuearticles values(3a);, C-alkylated coumarin insert ignore into journalissuearticles values(3aa); and structure 3ab formed by hydrolysis and decarboxylation from 3aa were formed products. In addition, the alkylation reaction of 3-OH, 5-OH, 6-OH, 7-OH, and 8-OH coumarin except 4-OH group produced a high yield.
Keywords : geranyloxycoumarin derivatives, 4 hydroxycoumarin, tautomeric keto enol forms, coumarin compounds, geranyl bromide