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Three-component condensation of cyclic 1,3-dicarbonyl compounds, N-phenacylpyridinium salts, and isatins or aromatic aldehydes as a method for the synthesis of novel condensed 2-aroyl-2,3-dihydrofurans

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Chemistry of Heterocyclic Compounds Aims and scope

Three-component condensation of in situ generated pyridinium aroylmethylides with isatins or aromatic aldehydes and cyclic 1,3-dicarbonyl compounds gave a series of condensed 2-aroyl-2,3-dihydrofurans. The reaction proceeds diastereoselectively and represents a cascade process involving the Knoevenagel condensation, the carbo-Michael reaction, and intramolecular nucleophilic substitution. The possibility of reductive rearrangement of spirocyclic furanyl-substituted oxindole into a pyran derivative by the action of zinc in acetic acid was shown.

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The study was carried out with the financial support of the Russian Foundation for Basic Research within the framework of the scientific project No. 19-03-01024 using the scientific equipment of the Center for Collective Use “Investigation of the physico-chemical properties of substances and materials” of Samara State Technical University.

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  1. Samara State Technical University, 244 Molodogvardeyskaya St, Samara, 443100, Russia

    Dmitry V. Osipov, Maxim R. Demidov, Vitaly A. Osyanin & Yury N. Klimochkin

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  1. Dmitry V. Osipov
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  2. Maxim R. Demidov
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  3. Vitaly A. Osyanin
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  4. Yury N. Klimochkin
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Correspondence to Vitaly A. Osyanin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(10), 1045–1050

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Osipov, D.V., Demidov, M.R., Osyanin, V.A. et al. Three-component condensation of cyclic 1,3-dicarbonyl compounds, N-phenacylpyridinium salts, and isatins or aromatic aldehydes as a method for the synthesis of novel condensed 2-aroyl-2,3-dihydrofurans. Chem Heterocycl Comp 57, 1045–1050 (2021). https://doi.org/10.1007/s10593-021-03020-3

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