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Updated: Sep 27, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Synthesis of Furan and Benzene Derivatives Containing Unsaturated Substituents with Electron-Withdrawing Groups, and
Mikhail V Kalyaev1,2, Irina A Boyarskaya1, Alexander Yu Ivanov3
1Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.
Abstract:
Furan-2-yl substituted ethenes and conjugated butadienes containing two geminal electron-withdrawing groups, as well as phenylbutadienes with two electron acceptors, were synthesized from the corresponding aldehydes and various β-dicarbonyl compounds via aldol condensation. Reactions of these ethenylfurans and methyl 3-(benzofuran-2-yl)propenoate with arenes in triflic acid (TfOH) yield arylated 2,3-dihydrofurans and 2,3-dihydrobenzofurans, representing a novel synthetic approach to these dihydro derivatives. In contrast, analogous reactions of furanyl- and phenylbutadienes result in carbon-carbon bond cleavage through retro-aldol and related acid-promoted processes. We propose plausible multistep mechanisms and cationic intermediates for these transformations. The synthesized furans and related compounds, at a concentration of 64 μg/mL, exhibit moderate antimicrobial activity against the yeast-like fungus Candida albicans.
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