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Copper-Catalyzed Annulation Reaction of Alkenes and <i>N</i>-Alkyl(aryl)-1-(methylthio)-2-nitroethenamine: an Approach for the Synthesis of Isoxazole Derivatives

Zhengbing Pan, Kaimin Mao, Guang‐Zhou Zhu, Chang Wang, Jinpeng Zhang, Liangce Rong

2020The Journal of Organic Chemistry17 citationsDOI

Abstract

A copper-catalyzed annulation reaction to access a variety of isoxazoles from alkenes and oxazete in situ generated from N-alkyl(aryl)-1-(methylthio)-2-nitroethenamine was reported. A plausible mechanism underlying the formation of the product was proposed, which represented a new approach for the construction of isoxazolines. This reaction was capable of tolerating alkenes bearing various substituents, which showed a relatively broad substrate scope with good functional group compatibility.

Topics & Concepts

ChemistryAnnulationArylAlkylIsoxazoleCatalysisOrganic chemistryFunctional groupMedicinal chemistryCombinatorial chemistryCopperPolymerSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques