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Three-component reaction of Δ1-pyrrolines, electron-deficient acetylenes, and NH-pyrroles. Synthesis of 2-(pyrrolyl)pyrrolidinyl acrylonitriles and enones

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Abstract

Addition of NH-pyrroles acting as electrophiles to zwitterionic adducts of Δ1-pyrrolines and electron-deficient acetylenes (20–25 °C, 4–30 h) gave 2-(pyrrol-1-yl)pyrrolidin-1-ylacrylonitriles and 2-(pyrrol-1-yl)pyrrolidin-1-ylenones in 18–48% yields.

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Acknowledgments

The main results were obtained with the use of the equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

Funding

This work was performed in the framework of the scientific research topics of A. E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences (Registration No. 121021000199-6).

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    L. A. Oparina, N. A. Kolyvanov, I. A. Ushakov & B. A. Trofimov

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  1. L. A. Oparina
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  2. N. A. Kolyvanov
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  3. I. A. Ushakov
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  4. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 1, pp. 141–145, January, 2024.

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Oparina, L.A., Kolyvanov, N.A., Ushakov, I.A. et al. Three-component reaction of Δ1-pyrrolines, electron-deficient acetylenes, and NH-pyrroles. Synthesis of 2-(pyrrolyl)pyrrolidinyl acrylonitriles and enones. Russ Chem Bull 73, 141–145 (2024). https://doi.org/10.1007/s11172-024-4125-x

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  • DOI: https://doi.org/10.1007/s11172-024-4125-x

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