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New synthesis of 3,3-disubstituted piperidin-2-ones from esters and 1-(3-halopropyl)-2,5-dimethylpyrroles

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Abstract

3,3-Disubstituted piperidin-2-ones were obtained by alkylation of carboxylic acid esters with 1-(3-halopropyl)-2,5-dimethylpyrroles using lithium diisopropylamide as a base followed by the removal of 2,5-dimethylpyrrole protection and intramolecular cyclization. The overall yields of the target products amounted to 78% in two synthetic steps.

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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

    V. D. Gvozdev, K. N. Shavrin & O. M. Nefedov

Authors
  1. V. D. Gvozdev
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  2. K. N. Shavrin
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  3. O. M. Nefedov
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Correspondence to V. D. Gvozdev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2108–2113, November, 2019.

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Gvozdev, V.D., Shavrin, K.N. & Nefedov, O.M. New synthesis of 3,3-disubstituted piperidin-2-ones from esters and 1-(3-halopropyl)-2,5-dimethylpyrroles. Russ Chem Bull 68, 2108–2113 (2019). https://doi.org/10.1007/s11172-019-2674-1

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  • DOI: https://doi.org/10.1007/s11172-019-2674-1

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