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Three-component synthesis of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones and their reductive rearrangement into 4H,5H-thiochromeno[4,3-b]pyran-5-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Three-component condensation of in situ generated pyridinium acyl methylides with aromatic aldehydes and 4-hydroxythiocoumarin led to a series of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones. The reaction proceeds diastereoselectively with the formation of trans-isomers and represents a cascade process involving the Knoevenagel condensation, carbo-Michael reaction, and intramolecular nucleophilic substitution. The subsequent redox rearrangement of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones by the action of Zn and ZrCl4 grants access to 4H,5H-thiochromeno[4,3-b]pyran-5-ones.

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

    Maxim R. Demidov, Anastasiya N. Dobrokvashina, Dmitry V. Osipov, Vitaly А. Osyanin & Yuri N. Klimochkin

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  1. Maxim R. Demidov
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  2. Anastasiya N. Dobrokvashina
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  3. Dmitry V. Osipov
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  4. Vitaly А. Osyanin
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  5. Yuri N. Klimochkin
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Correspondence to Vitaly А. Osyanin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 568–573

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Demidov, M.R., Dobrokvashina, A.N., Osipov, D.V. et al. Three-component synthesis of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones and their reductive rearrangement into 4H,5H-thiochromeno[4,3-b]pyran-5-ones. Chem Heterocycl Comp 57, 568–573 (2021). https://doi.org/10.1007/s10593-021-02944-0

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