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Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and chlorosulfanylarenes

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Abstract

Intramolecular cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides on heating in polyphosphoric acid afforded 8-aryl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones and 5-aryl-1-(thiophen-3-yl)pyrrolidin-2-ones. Cyclofunctionalization of the title compounds with (chlorosulfanyl)benzene and 4-(chlorosulfanyl)-toluene led to the formation of 8-aryl-7-arylsulfanyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones or their mixtures with 5-aryl-4-arylsulfanyltetrahydrofuran-2-ones. 1-(Chlorosulfanyl)-4-nitrobenzene reacted with 4-(4-methylphenyl)-N-(thiophen-3-yl)but-3-enamide and 4-(4-fluorophenyl)-N-(thiophen-3-yl)but-3-enamide to give 5-(4-methylphenyl)-4-(4-nitrophenylsulfanyl)-1-(thiophen-3-yl)pyrrolidin-2-one and 5-(4-fluorophenyl)-4-(4-nitrophenylsulfanyl)tetrahydrofuran-2-one, respectively.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02094, Ukraine

    I. Yu. Danilyuk, R. I. Vas’kevich & M. V. Vovk

  2. “Enamine” Scientific Production Association, ul. Chervonotkats’ka 78, Kiev, 02094, Ukraine

    R. I. Vas’kevich

  3. “Kyiv Polytechnic Institute” National Technical University of Ukraine, pr. Pobedy 37, Kiev, 03056, Ukraine

    A. I. Vas’kevich

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

Correspondence to R. I. Vas’kevich.

Additional information

Original Russian Text © I.Yu. Danilyuk, R.I. Vas’kevich, A.I. Vas’kevich, M.V. Vovk, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 7, pp. 993–998.

For communication VII, see [1].

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Danilyuk, I.Y., Vas’kevich, R.I., Vas’kevich, A.I. et al. Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and chlorosulfanylarenes. Russ J Org Chem 52, 987–992 (2016). https://doi.org/10.1134/S1070428016070113

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  • DOI: https://doi.org/10.1134/S1070428016070113

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