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Synthesis of Spiro[pyrrole–pyrrolizidines] by 1,3-Dipolar Cycloaddition of Azomethine Ylides to 3-Ylidenepyrrol-2-ones

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Abstract

The Knoevenagel condensation of 1H-pyrrole-2,3-diones with malononitrile gave 3-(dicyanomethylidene)-2,3-dihydro-1H-pyrrole-2-ones which were brought into 1,3-dipolar cycloaddition with azomethine ylides generated in situ from substituted benzaldehydes and proline or sarcosine. The cycloaddition involved the C3=C(CN)2 exocyclic double bond to afford regioisomeric spiro[pyrrole-3,2′-pyrrolizines] and spiro[pyrrole-3,1′-pyrrolizines] or 2,7-diazaspiro[4.4]nonane derivative.

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Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-13-00290).

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Authors and Affiliations

  1. Perm State University, 614990, Perm, Russia

    A. A. Moroz, M. V. Dmitriev & A. N. Maslivets

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  1. A. A. Moroz
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  2. M. V. Dmitriev
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  3. A. N. Maslivets
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Correspondence to A. N. Maslivets.

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Moroz, A.A., Dmitriev, M.V. & Maslivets, A.N. Synthesis of Spiro[pyrrole–pyrrolizidines] by 1,3-Dipolar Cycloaddition of Azomethine Ylides to 3-Ylidenepyrrol-2-ones. Russ J Org Chem 56, 1166–1173 (2020). https://doi.org/10.1134/S1070428020070076

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