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On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions: A Critical Review
Article

Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions

1
Molecular Modeling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, El Jadida 24000, Morocco
2
Laboratory of Chemical Processes and Applied Materials, Polydisciplinary Faculty, Sultan Moulay Slimane University, Beni-Mellal 23000, Morocco
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Organic and Analytical Chemistry Laboratory, Faculty of Science and Technology, Sultan Moulay Slimane University, Beni-Mellal 23000, Morocco
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Department of Elementary Science Education, Faculty of Education, Kocaeli University, Kocaeli 41380, Turkey
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Department of Organic Chemistry, University of Valencia, Dr. Moliner 50, 46100 Valencia, Spain
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Department of Organic Chemistry, Faculty of Sciences, Chouaib Doukkali University, El Jadida 24000, Morocco
*
Author to whom correspondence should be addressed.
Received: 21 October 2020 / Revised: 27 November 2020 / Accepted: 21 December 2020 / Published: 4 January 2021
(This article belongs to the Special Issue Cycloaddition Reaction in Organic Synthesis)
The regioselectvity and the mechanism of the (32CA) cycloadditions reactions of 1-bromo-4-vinylbenzene 1 and 1-chloro-4-vinylbenzene 2 with benzonitrile oxide 3 were investigated under the molecular electron density theory (MEDT) at the B3LYP/6-311++G(d,p) computational level. Evaluation of the ELF reveals that these zwitterionic type (zw-type) 32CA reactions take place in a two-stage one-step mechanism. This MEDT study shows that the meta isoxazolines are kinetically and thermodynamically favored over the ortho ones, these 32CA reactions being completely regioselective, in agreement with experimental outcomes. In addition, the efficiency of isoxazolines against SARS-CoV-2 have been also investigated. According to the docking analysis, the present study concludes that 5-(p-bromophenyl)-3-phenyl-2-isoxazoline (B-m) shows better interactions for the inhibition of SARS-CoV-2 in comparison to chloroquine. View Full-Text
Keywords: 2-isoxazoline; MEDT; regioselectivity; SARS-CoV-2; DFT; ELF 2-isoxazoline; MEDT; regioselectivity; SARS-CoV-2; DFT; ELF
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MDPI and ACS Style

El Idrissi, M.; El Ghozlani, M.; Eşme, A.; Ríos-Gutiérrez, M.; Ouled Aitouna, A.; Salah, M.; El Abdallaoui, H.E.A.; Zeroual, A.; Mazoir, N.; Domingo, L.R. Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions. Organics 2021, 2, 1-16. https://0-doi-org.brum.beds.ac.uk/10.3390/org2010001

AMA Style

El Idrissi M, El Ghozlani M, Eşme A, Ríos-Gutiérrez M, Ouled Aitouna A, Salah M, El Abdallaoui HEA, Zeroual A, Mazoir N, Domingo LR. Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions. Organics. 2021; 2(1):1-16. https://0-doi-org.brum.beds.ac.uk/10.3390/org2010001

Chicago/Turabian Style

El Idrissi, Mohammed, Mohamed El Ghozlani, Asli Eşme, Mar Ríos-Gutiérrez, Anas Ouled Aitouna, Mohammed Salah, Habib E.A. El Abdallaoui, Abdellah Zeroual, Noureddine Mazoir, and Luis R. Domingo 2021. "Mpro-SARS-CoV-2 Inhibitors and Various Chemical Reactivity of 1-Bromo- and 1-Chloro-4-vinylbenzene in [3 + 2] Cycloaddition Reactions" Organics 2, no. 1: 1-16. https://0-doi-org.brum.beds.ac.uk/10.3390/org2010001

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