Synthesis of New Trifluoromethylated Furans, Dihydrofurans and Butenolides Starting from γ-Ketothioesters and Diisopropylamine

Abstract

γ-Ketothioesters were easily transformed into furans, dihydrofurans or butenolides by simple treatment with diisopropyl­amine in diethyl ether. The substitution pattern of the starting material has a great influence on the outcome of the reaction. Possible mechanisms for the formation of the heterocycles were proposed. The structures of all new compounds were ascribed using usual NMR data (¹⁹F, ¹H, ¹³C NMR), X-ray diffraction analysis and ¹H-¹H NOE experiments.

Key words

fluorine - heterocycle - furan - dihydrofuran - butenolide

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