Isocyanide Heterodimerization-Triggered Three-Component Reaction: Diversity-Oriented Synthesis of Quinoxalines
Lan Bao, Min Li, Lianshun Zhang, Yating Xue, Jinhuan Dong, Xianxiu Xu
Abstract
Known isocyanide-based multicomponent reactions (IMCRs) are usually triggered by addition of the isocyano group to the strong electrophilic component. We herein report a new isocyanide-based three-component reaction, in which an unprecedented quinoxaline-based zwitterionic intermediate is generated from the chemoselective heterodimerization of weak electrophilic ortho -diisocyanoarenes and common isocyanides. This reactive zwitterion could react in situ with various trapping agents to furnish a range of structurally diverse quinoxalines.
Topics & Concepts
IsocyanideChemistryZwitterionElectrophileUgi reactionCombinatorial chemistryQuinoxalineComponent (thermodynamics)MoleculeStereochemistryOrganic chemistryCatalysisPhysicsThermodynamicsMulticomponent Synthesis of HeterocyclesSynthesis and Biological EvaluationSynthesis of heterocyclic compounds