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Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides

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Abstract

Sterically nonhindered N-alkyl(aryl)amides of cinnamylacetic acid in the reaction with phenyl(4-tolyl)sulfenyl chlorides in acetic acid in the presence of lithium perchlorate undergo a selective cyclization into 5-arylsulfanyl-6-phenylpiperidin-2-ones. Under similar conditions the reaction with arylsulfenyl chlorides of amides containing bulky substituents at the nitrogen atom resulted in 5-arylsulfanyl-6-phenyltetrahydropyran-2-iminium perchlorates, which by treatment with aqueous ethanol were converted into the corresponding derivatives of pyran-2-ones.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 02094, Ukraine

    A. I. Vas’kevich, N. M. Tsizorik, E. B. Rusanov, V. I. Stanitets & M. V. Vovk

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  1. A. I. Vas’kevich
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  2. N. M. Tsizorik
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  3. E. B. Rusanov
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  4. V. I. Stanitets
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  5. M. V. Vovk
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Correspondence to A. I. Vas’kevich.

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Original Russian Text © A.I. Vas’kevich, N.M. Tsizorik, E.B. Rusanov, V.I. Stanitets, M.V. Vovk, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 8, pp. 1130–1135.

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Vas’kevich, A.I., Tsizorik, N.M., Rusanov, E.B. et al. Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides. Russ J Org Chem 47, 1146–1152 (2011). https://doi.org/10.1134/S1070428011080057

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  • DOI: https://doi.org/10.1134/S1070428011080057

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