Metallation and reaction of 4,5-dicyanoimidazoles with alkyllithium reagents

The conditions required for selective lithiation at the 2-position of 4,5-dicyanoimidazoles are described in detail. The course of the reaction of alkyllithium reagents with 4,5-dicyanoimidazoles depends on the temperature, the number of equivalents of alkyllithium and whether the 1-nitrogen is protected. Under certain circumstances, the alkyllithium reagent adds to one of the cyano groups giving cyanoimidazole ketones.