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A facile transition-metal-free protocol to form 2-iminoimidazo[1, 2-a]-pyridines bearing a –CHBr2 group and an aza-quaternary carbon center at the 3 position from N-(2-pyridyl)amidines substrates, in which the new heterocyclic skeletons constructed from amidines via radical reactions or nucleophilic substitution reactions are promoted only by CBr4 under mild conditions, is demonstrated. The reactions were realized by intramolecular CDC reaction involving C–N and C–C bond formation via the sequential C(sp3)–H bifunctionalization mode on the same carbon atom under mild conditions. Moreover, this work also provides an excellent and representative example for CBr4 as an efficient reagent to initiate radical reactions under initiator-free conditions or to give rise to nucleophilic substitution reactions only by base.

A new, step-economical and operationally simple access to unsubstituted 1,2-dihydroisoquinolin-3(4H)-imines by Cu-catalyzed MCRs under mild conditions is described. In addition, selective hydrolysis of imines to the corresponding 1,2-dihydroisoquinolin-3(4H)-ones under refluxed conc. HCl has also been investigated.