The Bifunctionality of Tetramethylguanidine Enables the Synthesis of Poly Substituted Imidazolinones from Ketones.

A novel strategy for the efficient construction of polysubstituted imidazolinones from simple ketones was developed based on the bifunctional role of tetramethylguanidine (TMG). In this reaction, TMG served simultaneously as an organic base and a structural unit precursor, which react in situ with a cyanating reagent to generate a new type of nucleophilic intermediate, followed by condensation and cyclization with ketones. This protocol features readily available starting materials, simple operation and broad substrate scope.