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A MEDT study of the mechanism and selectivity of the hetero-Diels–Alder reaction between 3-benzoylpyrrolo[1,2-c][1,4]-benzoxazine-1,2,4-trione and vinyl acetate

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Chemistry of Heterocyclic Compounds Aims and scope

The chemo-, regio-, and stereoselectivity of the hetero-Diels–Alder reaction between 3-benzoylpyrrolo[1,2-c][1,4]benzoxazine-1,2,4-trione and vinyl acetate, has been investigated within molecular electron density theory at the B3LYP/6-311(d,p) level of theory. The conceptual density functional theory reactivity indices, as well as the activation and reaction energies have been analyzed, and five possible reaction paths for this cycloaddition reaction, resulting from the presence of three heterodiene frameworks in the molecule of the diene reactant have been studied. The conceptual density functional theory analysis indicates that vinyl acetate acts as a nucleophile and 3-benzoylpyrrolo[1,2-c][1,4]benzoxazine-1,2,4-trione acts as a strong electrophile. The computed activation and reaction energies reveal that that this reaction is chemo-, stereo-, and regioselective, which is consistent with the experimental findings. Topological electron localization function analysis was used to look into how the electron densities were reorganized along the preferred reaction path. According to this analysis, the reaction takes place through a two-stage one-step mechanism.

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Authors and Affiliations

  1. Molecular Modeling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P. O. Box 20, 24000, El Jadida, Morocco

    Soukaina Ameur, Ali Barhoumi, Anas Ouled Aitouna, Habib El Alaoui El Abdallaoui & Abdellah Zeroual

  2. Laboratory of Bioorganic Chemistry, Department of Chemistry Faculty of Sciences, Chouaïb Doukkali University, P. O. Box 20, 24000, El Jadida, Morocco

    Soukaina Ameur, Anas Ouled Aitouna & Noureddine Mazoir

  3. Department of Organic Chemistry, University of Valencia, Dr. Moliner 50, 46100, Burjassot, Valencia, Spain

    Mar Ríos-Gutiérrez & Luis R. Domingo

  4. Laboratory of Physical Chemistry of Materials, Ben M’Sick Faculty of Sciences, Hassan II University, Casablanca, Morocco

    Mohammed Elalaoui Belghiti

  5. Laboratory of Nernest Technology, 163 Willington Street, Sherbrooke, QC, J1H5C7, Canada

    Mohammed Elalaoui Belghiti

  6. Department of Botany and Microbiology, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia

    Asad Syed

Authors
  1. Soukaina Ameur
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  2. Ali Barhoumi
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  3. Mar Ríos-Gutiérrez
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  4. Anas Ouled Aitouna
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  7. Mohammed Elalaoui Belghiti
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  8. Asad Syed
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  9. Abdellah Zeroual
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Corresponding author

Correspondence to Abdellah Zeroual.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(3), 165–170

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Ameur, S., Barhoumi, A., Ríos-Gutiérrez, M. et al. A MEDT study of the mechanism and selectivity of the hetero-Diels–Alder reaction between 3-benzoylpyrrolo[1,2-c][1,4]-benzoxazine-1,2,4-trione and vinyl acetate. Chem Heterocycl Comp 59, 165–170 (2023). https://doi.org/10.1007/s10593-023-03178-y

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