Sustainable synthesis of highly diastereoselective & fluorescent active spirooxindoles catalyzed by copper oxide nanoparticle immobilized on microcrystalline cellulose
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Date
2022-05-18T00:00:00
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John Wiley and Sons Ltd
Abstract
Composites of copper oxide nanoparticles immobilized on microcrystalline cellulose (Cu2O@MCC) were synthesized and studied for their catalytic activity toward 1,3-dipolar cycloaddition reaction. Azomethine ylide was in situ generated from isatin and 1,2,3,4-tetrahydroisoquinoline (THIQ) and styrylisoxazoles/chalcones used as dipolarphiles in one-pot synthesis of novel spiro polycyclic heterocyclic compounds. Cu2O@MCC showed excellent catalytic activity on 20 mg of composite with 30% loading of copper on MCC. The scale-up and recyclability experiment on the 10�mmol scale revealed the sustainability of composite even after four consecutive cycles. The products were fluorescent active, obtained in good to excellent yield with high regio and diastereoselectivity. The relevant features of the developed protocol are eco-friendly with a wide range of substrate scope and shorter reaction time. � 2022 John Wiley & Sons Ltd.
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Keywords
1,3-dipolar cycloaddition, Chalcone, Cu<sub>2</sub>O@MCC, fluorescence, Styrylisoxazole