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

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 the...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2023-03, Vol.59 (3), p.165-170
Main Authors: Ameur, Soukaina, Barhoumi, Ali, Ríos-Gutiérrez, Mar, Aitouna, Anas Ouled, Abdallaoui, Habib El Alaoui El, Mazoir, Noureddine, Belghiti, Mohammed Elalaoui, Syed, Asad, Zeroual, Abdellah, Domingo, Luis R.
Format: Article
Language:English
Subjects:
Activation energy
Analysis
Benzoxazines
Cancer
Chemical tests and reagents
Chemistry
Chemistry and Materials Science
Chemotherapy
Cycloaddition
Density functional theory
Density functionals
Diels-Alder reaction
Diels-Alder reactions
Electron density
Function analysis
Nucleophiles
Organic Chemistry
Pharmacy
Stereoselectivity
Vinyl acetate
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03178-y