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Two novel copper-mediated annulations of 2-(2-halophenyl)-1H-indoles with(aryl)methanamines or 2-halophenols have been accomplished.These reactions provide two efficient and regioselective methods for the synthesis of indolo[1,2-c]quinazoline derivatives[1] or fused dibenzo[b,f][1,4]oxazepines[2] from readily available chemical reagents.