Synthesis of Benzo[4,5]imidazo[1,2-]pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization.

2-(2-Bromovinyl)benzimidazoles and 2-(2-bromophenyl)benzimidazoles react with cyanamide by microwave irradiation in dimethylformamide in the presence of a catalytic amount of CuI along with a base to give the corresponding benzo[4,5]imidazo[1,2-]pyrimidin-1-amines and benzo[4,5]imidazo[1,2-]quinazolin-6-amines, respectively, in moderate to good yields. 2-(2-Bromophenyl)indoles also react with cyanamide under similar conditions to afford indolo[1,2-]quinazolin-6-amines. The reaction pathway seems to proceed via a sequence such as intermolecular C-N coupling, C-N formative cyclization, and tautomerization.