Journal
ORGANIC LETTERS
Volume 25, Issue 13, Pages 2366-2371Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00794
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We report a new isocyanide-based three-component reaction that generates an unprecedented zwitterionic intermediate from the chemoselective heterodimerization of weak electrophilic ortho-diisocyanoarenes and common isocyanides. This reactive zwitterion can react in situ with various trapping agents to form a range of structurally diverse quinoxalines.
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.
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