Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs(2)CO(3)-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

The synthesis of benzimidazo[2,1-b]benzoselenoazoles is described. The novel ring-closure reaction of 1-(2-bromoaryl)benzimidazoles with Se powder is promoted by Cs(2)CO(3) (2 equiv) in DMF at 150 °C. Moreover, the obtained tetracyclic heterocycles are all novel compounds. Single-crystal X-ray analysis of the parent benzimidazo[2,1-b]benzoselenoazole revealed that the tetracyclic ring is almost planar. Absorption spectroscopy data of the benzimidazo[2,1-b]benzoselenoazoles showed the λ(max) was dependent on the number of rings.