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Fused pyrimidine systems: XVII. Arylsulfenylation of 5-allylpyrimidine-4(3H)-one derivatives. Synthesis of arylsulfanyl-substituted 5,6-dihydrofuro[2,3-d]- and 6,7-dihydro-5H-pyrano[2,3-d]pyrimidines

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Abstract

5-Allylpyrimidine-4-ones react with arylsulfenyl chlorides in dichloromethane with the formation of 5-[(2-arylsulfanyl)-3-chloropropyl]-pyrimidine-4-ones that under the action of sodium acetate undergo cyclization into 6-arylsulfanyl-6,7-dihydro-5H-pyrano[2,3-d]pyrimidines. At performing similar reactions in nitromethane an intramolecular electrophilic cyclization occurs affording 6-[(arylsulfanyl)methyl]-5,6-dihydrofuro[2,3-d]pyrimidines.

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Authors and Affiliations

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

    A. I. Vas’kevich & M. V. Vovk

  2. National Technical University of Ukraine, Kiev Polytechnical University, Kiev, Ukraine

    A. I. Vas’kevich

Authors
  1. A. I. Vas’kevich
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  2. M. V. Vovk
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Correspondence to A. I. Vas’kevich.

Additional information

Original Russian Text © А.I. Vas’kevich, М.V. Vovk, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 271–276.

For communication XVI, see [1].

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Vas’kevich, A.I., Vovk, M.V. Fused pyrimidine systems: XVII. Arylsulfenylation of 5-allylpyrimidine-4(3H)-one derivatives. Synthesis of arylsulfanyl-substituted 5,6-dihydrofuro[2,3-d]- and 6,7-dihydro-5H-pyrano[2,3-d]pyrimidines. Russ J Org Chem 53, 270–276 (2017). https://doi.org/10.1134/S1070428017020221

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  • DOI: https://doi.org/10.1134/S1070428017020221

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