Synthesis of Benzo[4,5]imidazo[1,2‑c]pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C–N Coupling and Cyclization
2017-06-26T11:50:27Z (GMT) by
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-c]pyrimidin-1-amines and benzo[4,5]imidazo[1,2-c]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-c]quinazolin-6-amines. The reaction pathway seems to proceed via a sequence such as intermolecular C–N coupling, C–N formative cyclization, and tautomerization.