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Selective Synthesis of 2-Methylidenepyrrol-3-Ones from Diynones and Amines

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Chemistry of Heterocyclic Compounds Aims and scope

Addition of primary amines to 1-phenyl-5-trimethylsilylpenta-1,4-diyn-3-one with subsequent cyclization affords 5-phenyl-2-(trimethylsilylmethylidene)-1,2-dihydro-3H-pyrrol-3-ones. Both electron-rich and electron-deficient anilines and alkyl amines provide regio- and stereoselective formation of single product in high yields. The two-step transformation benefits from full atom economy, operational simplicity, and no need for additives and catalysts.

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This work was supported by the Russian Science Foundation (grant 18-73-00089).

NMR, HRMS, and XRD analyses were performed at Saint Petersburg State University Center for Magnetic Resonance, Center for Chemical Analysis and Materials Research, and X-ray Diffraction Center, respectively.

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Authors and Affiliations

  1. Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Ave., Saint Petersburg, 198504, Russia

    Alena S. Pankova, Nadezhda D. Cherepanova, Pavel Golubev & Mikhail A. Kuznetsov

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  1. Alena S. Pankova
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  2. Nadezhda D. Cherepanova
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  3. Pavel Golubev
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  4. Mikhail A. Kuznetsov
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Correspondence to Alena S. Pankova.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 672–675

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Pankova, A.S., Cherepanova, N.D., Golubev, P. et al. Selective Synthesis of 2-Methylidenepyrrol-3-Ones from Diynones and Amines. Chem Heterocycl Comp 55, 672–675 (2019). https://doi.org/10.1007/s10593-019-02515-4

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  • DOI: https://doi.org/10.1007/s10593-019-02515-4

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