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Study on formation mechanism of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylic esters

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Abstract

The mechanism of formation of methyl (4RS,6SR)-2-(4-bromophenyl)-5,5-dicyano-4,6-bis(4-methylphenyl)-1,4,5,6-tetrahydropyridine-3-carboxylate was estimated. Formation of 1,4,5,6-tetrahydropyridine moiety proceeds through a sequence of the Michael addition, the Mannich reaction, stereoselective cyclization to polysubstituted (2SR,3RS,4SR,6RS)-2-hydroxypiperidine, dehydration to (3RS,4SR,6RS)-3,4,5,6-tetrahydropyridine, and isomerization. Polysubstituted (4RS,6SR)-1,4,5,6-tetrahydropyridine was found to be thermodynamically more stable than isomeric (3RS,4SR,6RS)-3,4,5,6-tetrahydropyridine.

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Funding

The study was financially supported by the Russian Science Foundation (Project No. 17-73-20260).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    K. A. Karpenko, T. M. Iliyasov, A. N. Fakhrutdinov, A. S. Akulinin, M. N. Elinson & A. N. Vereshchagin

Authors
  1. K. A. Karpenko
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  2. T. M. Iliyasov
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  3. A. N. Fakhrutdinov
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  4. A. S. Akulinin
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Correspondence to A. N. Vereshchagin.

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No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1279–1283, June, 2022.

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Karpenko, K.A., Iliyasov, T.M., Fakhrutdinov, A.N. et al. Study on formation mechanism of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylic esters. Russ Chem Bull 71, 1278–1283 (2022). https://doi.org/10.1007/s11172-022-3531-1

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  • DOI: https://doi.org/10.1007/s11172-022-3531-1

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