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Regioselective synthesis of substituted tetrahydrochromeno[2,3-d]pyrimidin-2-ones and -pyrimidine-2-thiones

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Abstract

The regioselective synthesis of the substituted (4R*,10aR*)-4-aryltetrahydro-2H-chromeno[2,3-d]pyrimidin-2-ones, -pyrimidine-2-thiones and (4R*,5R*,6R*)-5-acetyl-6-aryl-4-(2,4-dihydroxyphenyl)hexahydropyrimidin-2-ones, -hexahydropyrimidine-2-thiones by the reaction of the appropriate 5-acetyl-4-aryldihydropyrimidin-2-ones and -pyrimidine-2-thiones with 1,3-benzenediols was described. A plausible mechanism of the acid catalyzed rearrangement of resorcinol-substituted hexahydropyrimidin-2-ones and -pyrimidine-2-thiones to chromeno[2,3-d]pyrimidin-2-ones and -pyrimidine-2-thiones, respectively, was suggested.

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Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovskii prosp., 150023, Yaroslavl, Russian Federation

    E. S. Makarova, M. V. Kabanova, S. I. Filimonov & Zh. V. Chirkova

  2. Center for Transfer of Pharmaceutical Technologies, Yaroslavl State Pedagogical University named after K. D. Ushinsky, 108/1 ul. Respublicanskaya, 150000, Yaroslavl, Russian Federation

    S. A. Ivanovsky & A. A. Shetnev

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Build. 1, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. Yu. Suponitsky

  4. Plekhanov Russian University of Economics, 36 Stremyannoy per., 117997, Moscow, Russian Federation

    K. Yu. Suponitsky

Authors
  1. E. S. Makarova
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  2. M. V. Kabanova
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  3. S. I. Filimonov
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  4. Zh. V. Chirkova
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  5. S. A. Ivanovsky
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  6. A. A. Shetnev
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  7. K. Yu. Suponitsky
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Corresponding author

Correspondence to S. I. Filimonov.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 22-13-20085).

X-ray diffraction studies were performed in the framework of the State Tack No. 075-03-2023-642 of the Ministry of Science and Higher Education of the Russian Federation.

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, Vol. 72, No. 6, pp. 1454–1465, June, 2023.

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Makarova, E.S., Kabanova, M.V., Filimonov, S.I. et al. Regioselective synthesis of substituted tetrahydrochromeno[2,3-d]pyrimidin-2-ones and -pyrimidine-2-thiones. Russ Chem Bull 72, 1454–1465 (2023). https://doi.org/10.1007/s11172-023-3920-0

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  • DOI: https://doi.org/10.1007/s11172-023-3920-0

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