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Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation

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Abstract

Cinnamylacetamides reacted with arylsulfenyl chlorides in chloroform in the absence of LiClO4 affording 5-(arylsulfanyl)-6-phenylpiperidin-2-ones. Their reduction with a system LiAlH4-AlCl3 resulted in 3-(tolylsulfanyl)-1,2-diphenylpiperidine, and with Raney nickel, in 1-aryl-6-phenylpiperidin-2-ones. The latter treated with LiAlH4-AlCl3 were converted into 1-aryl-2-phenyl-piperidines. The oxidation of 5-(arylsulfanyl)-6-phenylpiperidin-2-ones with hydrogen peroxide in acetone led to the formation of 5-sulfinyl-, and with oxone, to 5-sulfonyl derivatives.

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Authors and Affiliations

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

    N. M. Tsizorik, R. I. Vas’kevich & M. V. Vovk

  2. National Technical University of Ukraine “KPI”, pr. Pobedy 37, Kiev, 03056, Ukraine

    A. I. Vas’kevich

Authors
  1. N. M. Tsizorik
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  2. A. I. Vas’kevich
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  3. R. I. Vas’kevich
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  4. M. V. Vovk
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Corresponding author

Correspondence to A. I. Vas’kevich.

Additional information

Original Russian Text © N.M. Tsizorik, A.I. Vas’kevich, R.I. Vas’kevich, M.V. Vovk, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 237–241.

For communication VI, see [1].

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Tsizorik, N.M., Vas’kevich, A.I., Vas’kevich, R.I. et al. Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation. Russ J Org Chem 51, 226–230 (2015). https://doi.org/10.1134/S1070428015020165

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  • DOI: https://doi.org/10.1134/S1070428015020165

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