Base-Catalyzed Chemoselective Substitution of <i>β</i>-Ketonitrile with Azodicarboxylates

Base-catalyzed nucleophilic substitution reactions of -ketonitrile with azodicarboxylates have been developed.A series of disubstituted C-N coupling products were obtained in good to excellent yields under Et3N catalysis.Monosubstitution C-N bond formation reaction catalyzed by K2CO3 also gave novel enol-based target products.This method is simple and mild, with good chemoselectivity, excellent substrate compatibility and tolerance for various functional groups, and achieves gram-scale synthesis.The reaction is a nucleophilic substitution process without the involvement of free radicals.