2018•Russian Journal of Organic ChemistryRequires access

Substituted Butanolides and Butenolides: XVII. Substituted 3-(Furan-2-ylmethylidene)furan-2(3H)-ones and 3-(Furan-2-ylmethylidene)dihydrofuran-2(3H)-ones

Larisa A. Badovskaya, Lyudmila N. Sorotskaya, Nadezhda D. Kozhina, T. Ya. Kaklyugina

Abstract

A number of furan-2-ylmethylidene-substituted lactones were synthesized by condensation of 5-alkylfuran-2(3 H )-ones and 4-alkyldihydrofuran-2(3 H )-ones with 5-substituted furan-2-carbaldehydes. The reactivity of furan-2(3 H )-ones was higher than that of furan-2(5 H )-ones due to formation of intermediate conjugated anion. The condensation of 4-alkyldihydrofuran-2(3 H )-ones with furan-2-carbaldehydes required more severe conditions than the condensation with furan-2(3 H )-ones. The substituent in the furan ring affects the reaction time and yield.

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Key concepts: Furan, Chemistry, Reactivity (psychology), Substituent, Yield (engineering), Condensation, Medicinal chemistry, Ring (chemistry)