Green and Expeditious Synthesis of Isoxazol-5(4H)-ones via Three-Component Reaction
Publish place: 26th Iranian Seminar on Organic Chemistry
Publish Year: 1397
نوع سند: مقاله کنفرانسی
زبان: English
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شناسه ملی سند علمی:
ISOC26_134
تاریخ نمایه سازی: 2 شهریور 1398
Abstract:
Organosulfonic acids demonstrate an important generation of organocatalysts in organic synthesis,which have been successfully applied in different types of acid-catalyzed organictransformations [1]. Isoxazole and its derivatives are good synthetic targets on account oftheir important applications, including pharmaceutical functions in medicine as antimicrobial,antiviral, anticancer, anti-inflammatory, immunomodulatory, anticonvulsant or anti-diabeticagents, pest control in agriculture, and also convertible to other heterocyclic compoundsthrough catalytic processes [2]. Multi-component reactions (MCRs) are one of the most syntheticallyareas in modern organic synthesis for the synthesis of high levels of molecular diversityfrom three or more substrates with a minimal number of operations. Some obviousadvantages of MCRs include atom-, and step-economy, cost-effectiveness, no need for isolationof intermediates, and manufacture of heterocyclic compounds with high diversity in onesynthetic step. These characteristics together with the associated reduction of waste make agreener alternative to multistep synthesis [3]. In the present work, catalytic amounts of 2-benzyl-1-sulfopyridin-1-ium have been used for the synthesis of isoxazol-5(4H)-ones througha MCR procedure. This eco-friendly, one-pot, three-component process was performed usingethyl acetoacetate, various aromatic aldehydes, and hydroxylamine hydrochloride as reactants,and above-mentioned catalyst under aqueous conditions (Fig. 1). The heterocyclicproducts were obtained in good to excellent yields and relatively shorter reaction times.
Authors
Mohadeseh Goli
School of Chemistry, Damghan University, Damghan, Iran
Hamzeh Kiyani
School of Chemistry, Damghan University, Damghan, Iran