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Green synthesis of 3,4‐disubstituted isoxazol‐5(4<i>H</i>)‐ones using ZnO@Fe<sub>3</sub>O<sub>4</sub> core–shell nanocatalyst in water

M. Shanshak, Srinivasa Budagumpi, J.G. Małecki, Rangappa S. Keri

2020Applied Organometallic Chemistry46 citationsDOI

Abstract

Abstract An effective and environmentally benign methodology for the synthesis of isoxazol‐5(4 H )‐one derivatives has been developed using a ZnO@Fe 3 O 4 core–shell nanocatalytic system. The one‐pot, multicomponent reaction of an aromatic/heterocyclic aldehyde, hydroxylamine hydrochloride and ethyl acetoacetate under aqueous conditions at slightly elevated temperature resulted in the formation of title compounds in extremely good yields. The present new protocol is environmentally friendly as it offers heterocyclization with some interesting promising features such as safety, atom efficiency, low cost, mild conditions, minimal waste, catalyst recyclability, water as a solvent, easy workup and possession of excellent functional group tolerance for the synthesisis of structurally diverse isoxazole derivatives. All products were characterized by spectral and analytical methods. A representative title derivative was studied for its structure by single crystal X‐ray diffraction method.

Topics & Concepts

ChemistryEthyl acetoacetateIsoxazoleAtom economyCatalysisHydroxylamine HydrochlorideEnvironmentally friendlyAqueous solutionAldehydeSolventOrthorhombic crystal systemGreen chemistryCrystal structureCombinatorial chemistryOrganic chemistryReaction mechanismBiologyEcologyMulticomponent Synthesis of HeterocyclesSynthesis and biological activitySynthesis and Biological Evaluation