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Twice as Nice: The Duff Formylation of Umbelliferone Revised.

ABSTRACT: More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff ortho-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 ortho-formylation of umbelliferone, yielding a mixture of ortho-formyl position isomers. Thorough studies on the separation of ortho-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.

SUBMITTER: Skarga VV

PROVIDER: S-EPMC8706561 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Twice as Nice: The Duff Formylation of Umbelliferone Revised.

Skarga Vladislav V VV Negrebetsky Vadim V VV Baukov Yuri I YI Malakhov Mikhail V MV

Molecules (Basel, Switzerland) 20211210 24

More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff ortho-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 ortho-formylation of umbelliferone, yielding a mixture of ortho-formyl position isomers. Thorough studies on the separation of ortho< ...[more]

PMID: 34946562

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