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Ring expansion of donor—acceptor cyclopropanes bearing arylcarbamoyl group into 1,5-diarylpyrrolidin-2-ones

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Abstract

The rearrangement of 2,N-diaryl-1-carbamoylcyclopropanecarboxylates upon their treatment with titanium(iv) chloride was found to proceed as ring expansion affording 1,5-diaryl-2-oxopyrrolidine-3-carboxylates. In the resulting products, the ester group can be easily removed via either the Krapcho reaction or alkaline hydrolysis followed by the thermal decarboxylation.

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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

    A. E. Vartanova, A. Yu. Plodukhin, M. A. Boichenko, V. V. Shorokhov & I. V. Trushkov

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, 1/3 Leninskie Gory, 119991, Moscow, Russian Federation

    A. Yu. Plodukhin, M. A. Boichenko, V. V. Shorokhov, S. S. Zhokhov & O. A. Ivanova

  3. Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology, and Immunology, 1 ul. Samory Mashela, 117997, Moscow, Russian Federation

    I. V. Trushkov

Authors
  1. A. E. Vartanova
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  2. A. Yu. Plodukhin
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  3. M. A. Boichenko
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  4. V. V. Shorokhov
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  5. S. S. Zhokhov
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  6. I. V. Trushkov
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  7. O. A. Ivanova
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Corresponding authors

Correspondence to I. V. Trushkov or O. A. Ivanova.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 21-13-00395).

NMR spectra were recorded at the Laboratory of Magnetic Tomography and Spectroscopy, Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University. IR and mass spectra were recorded at the Center for Collective Use of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the VI North Caucasus Organic Chemistry Symposium 2022 NCOCS-2022 (April 18–22, 2022, Stavropol, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2431–2440, November, 2022.

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Vartanova, A.E., Plodukhin, A.Y., Boichenko, M.A. et al. Ring expansion of donor—acceptor cyclopropanes bearing arylcarbamoyl group into 1,5-diarylpyrrolidin-2-ones. Russ Chem Bull 71, 2431–2440 (2022). https://doi.org/10.1007/s11172-022-3671-3

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  • DOI: https://doi.org/10.1007/s11172-022-3671-3

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