Abstract 2-Aminophenoxathiin undergoes easy condensation with different ω-bromoketones to give 2-aroylmethylaminophenoxathiins. These compounds give pyrrolo [2, 3-b] phenoxathiins by the Möhlau-Bischler cyclisation. Some carbazolo [2, 1-b] phenoxathiins were also synthesised from 7-oxo-7, 8, 9, 10-tetrahydrobenzo [b] phenoxathiin.