Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles

Maxim R. Demidov, Vitaly A. Osyanin*, Dmitry V. Osipov and Yuri N. Klimochkin

*Samara State Technical University, 443100 Samara, Russian Federation, Email: VOsyaninmail.ru

M. R. Demidov, V. A. Osyanin, D. V. Osipov, Y. N. Klimochkin, J. Org. Chem., 2021, 86, 7460-7476.

DOI: 10.1021/acs.joc.1c00423

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Abstract

A three-component reaction of β-ketonitriles, carbonyl- and semistabilized pyridinium ylide precursors, and aldehydes provides trans-4,5-dihydrofuran-3-carbonitriles in good yields in the presence of piperidine via cascade Knoevenagel condensation, Michael addition, and intramolecular S_N2 cyclization.

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Key Words

2,3-Dihydrofurans, Multicomponent Reactions

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ID: J42-Y2021