Twice As Nice: The Duff Formylation of Umbelliferone Revised

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Dec 24

PMID 34946562

Authors

Vladislav V Skarga

Vadim V Negrebetsky

Yuri I Baukov

Mikhail V Malakhov

Affiliations

Soon will be listed here.

Abstract

More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff -formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and resulted in unexpectedly rapid -formylation of umbelliferone, yielding a mixture of -formyl position isomers. Thorough studies on the separation of -formylated umbelliferones using chromatographic and recrystallization methods as well as the evaluation of their solubility in common organic solvents led to complete resolution of 8-formyl- and 6-formylumbelliferones. The precise protocol for simultaneous preparation, extraction, and purification of 8-formyl- and 6-formylumbelliferones is provided, and the prospective studies of biological and pharmacological activities of these compounds are synopsized.

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