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ORIGINAL RESEARCH article

Front. Chem.
Sec. Organic Chemistry
Volume 12 - 2024 | doi: 10.3389/fchem.2024.1472342

Sustainable Synthesis of Antibacterial 3-Aryl-2H-Benzo[b,1,4]oxazin-2ones via SNAr Csp 2 -Csp 2 Coupling

Provisionally accepted
Fatemeh Salehzadeh Fatemeh Salehzadeh 1Maryam Esmkhani Maryam Esmkhani 1Milad Noori Milad Noori 1Shahrzad Javanshir Shahrzad Javanshir 1*Aida Iraji Aida Iraji 2Mohammad Mahdavi Mohammad Mahdavi 3
  • 1 Iran University of Science and Technology, Tehran, Iran
  • 2 Shiraz University of Medical Sciences, Shiraz, Fars, Iran
  • 3 Tehran University of Medical Sciences, Tehran, Tehran, Iran

The final, formatted version of the article will be published soon.

    In the pursuit of sustainable synthetic methods, we applied nucleophilic aromatic substitution (SNAr) under microwave-assisted conditions to synthesize 3-aryl-2H-benzo [b][1,4]oxazin-2-one derivatives, including the natural product cephalandole A. This metal-free carbon-carbon coupling method demonstrates a more sustainable approach by eliminating the need for metal catalysts and offering efficient reaction conditions, resulting in good yields (55-82%) with reduced reaction times (7-12 min) and simplified workup processes.Regarding the critical need for new antibacterial agents against antibiotic-resistant pathogens, we conducted an in silico molecular docking study to evaluate the antibacterial potential of the synthesized derivatives. This computational approach allowed us to predict the binding affinity and interaction profiles of the compounds with key bacterial targets, identifying 3-(1H-indol-3-yl)-6-methyl-2H-benzo [b][1,4]oxazin-2one (6b) as a particularly promising candidate for further biological evaluation. By integrating sustainable synthesis with in silico antibacterial screening, this research contributes not only to the development of ecofriendly synthetic pathways in pharmaceutical chemistry but also to the urgent global effort to discover novel antibacterial agents.

    Keywords: Csp 2 -Csp 2 Cross-Coupling Reactions, Microwave-assisted organic synthesis, Nucleophilic aromatic substitution, antimicrobial, Natural Product cephalandole A

    Received: 29 Jul 2024; Accepted: 28 Oct 2024.

    Copyright: © 2024 Salehzadeh, Esmkhani, Noori, Javanshir, Iraji and Mahdavi. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

    * Correspondence: Shahrzad Javanshir, Iran University of Science and Technology, Tehran, Iran

    Disclaimer: All claims expressed in this article are solely those of the authors and do not necessarily represent those of their affiliated organizations, or those of the publisher, the editors and the reviewers. Any product that may be evaluated in this article or claim that may be made by its manufacturer is not guaranteed or endorsed by the publisher.