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Regio- and Diastereoselective [4+2]-Cycloaddition of 4,5-Diaroyl-1H-pyrrole-2,3-diones and Cyclopentadiene

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Abstract

Thermally initiated [4+2]-cycloaddition of 4,5-diaroyl-1H-pyrrole-2,3-dione and cyclopentadiene as a dienophile afforded substituted 5a,8,8a,8b-tetrahydro-1H-cyclopenta[5,6]pyrano[4,3-b]pyrrole-2,3-diones whose structure was determined by X-ray analysis of one of the products. The reaction was regio- and diastereoselective, and only one endo-hetero-Diels–Alder adduct was formed. The described reaction provides a convenient preparative route to difficultly accessible substituted cyclopenta[5,6]pyrano[4,3-b]pyrrole derivatives.

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Funding

This study was supported under financial support by the Perm Scientific and Educational Center “Rational Use of Earth’s Interior,” 2021.

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Authors and Affiliations

  1. Perm State University, 614068, Perm, Russia

    A. A. Moroz, D. I. Antonov, M. V. Dmitriev & A. N. Maslivets

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  1. A. A. Moroz
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  2. D. I. Antonov
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  3. M. V. Dmitriev
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  4. A. N. Maslivets
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Corresponding author

Correspondence to A. N. Maslivets.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 3, pp. 264–269 https://doi.org/10.31857/S0514749222030041.

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Moroz, A.A., Antonov, D.I., Dmitriev, M.V. et al. Regio- and Diastereoselective [4+2]-Cycloaddition of 4,5-Diaroyl-1H-pyrrole-2,3-diones and Cyclopentadiene. Russ J Org Chem 58, 282–286 (2022). https://doi.org/10.1134/S1070428022030046

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