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Abstract

Carboxylic acids bearing in α,β-position an oxirane ring functionality are, in fact, useful intermediates in the synthesis of biologically active compounds. Epoxidation of 4-(4-acetylamino/bromophenyl)-4-oxobut-2-enoic acids via ultrasound and microwave conditions afforded the corresponding oxirane derivatives. Synthesis of heterocyclic compounds via ultrasonic epoxidation of α,β-unsaturated carboxylic acid afforded the regioselective diastereomeric adducts of camphor and considered as key steps for antibacterial activity of the synthesized heterocyclic compounds. The steric factor plays an important role in regioselectivity. The structures of newly synthesized compounds were elucidated by elemental analysis and spectroscopic data. Six synthesized compounds showed strong antibacterial activity against Gram-positive and Gramnegative bacteria.

Keywords

Epoxide Ultrasound Microwave synthesis Furanones Pyridazinone Oxazinones HOMO energy

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Rizk, S., & Shaker, S. (2017). Ultrasonic and Solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as Antibacterial Agents Using Quantum Chemical Computation. Asian Journal of Organic & Medicinal Chemistry, 2(3), 117–124. https://doi.org/10.14233/ajomc.2017.AJOMC-P60
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