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Synthesis of Spiro[pyrrole-3,2'-pyrrolo[2,1-b]oxazoles] via 1,3-Dipolar Cycloaddition of 1H-Pyrrole-2,3-diones to Azomethine Ylides

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Abstract

The 1,3-dipolar cycloaddition of 1H-pyrrole-2,3-diones to azomethine ylides generated in situ by the condensation of L-proline and arylcarbaldehydes proceeds regio- and diastereoselectively to form substituted ethyl 1,2,5',6',7',7a'-hexahydro-3'H-spiro[pyrrole-3,2'-pyrrolo[2,1-b]oxazole]-4-carboxylates. The structure of the synthesized ethyl (3R*,3'R*,7a'S*)-3'-(4-bromophenyl)-2-oxo-1,5-diphenyl-1,2,5',6',7',7a'-hexahydro-3'H-spiro[pyrrole-3,2'-pyrrolo[2,1-b]oxazole]-4-carboxylate was confirmed by single crystal X-ray analysis.

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Funding

The work was financially supported by the Ministry of Education and Science of the Russian Federation (project no. FSNF-2023-0004) and the Russian Foundation for Basic Research and the Perm Krai (project no. 20-43-596008).

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Authors and Affiliations

  1. Perm State University, 614068, 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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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1427–1434 https://doi.org/10.31857/S0514749223110046.

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Moroz, A.A., Dmitriev, M.V. & Maslivets, A.N. Synthesis of Spiro[pyrrole-3,2'-pyrrolo[2,1-b]oxazoles] via 1,3-Dipolar Cycloaddition of 1H-Pyrrole-2,3-diones to Azomethine Ylides. Russ J Org Chem 59, 1867–1873 (2023). https://doi.org/10.1134/S1070428023110040

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