An efficient novel strategy for the heteroannulation of 6,7‐dihydropyrazolo[3,4‐b]carbazol‐8(1H,5H,9H)‐one 4 and 5‐N‐benzyl‐6,7‐dihydropyrazolo[3,4‐b]carbazol‐8(1H,9H)‐one 5 has been developed to allow the incorporation of pyrazole, isoxazole, pyrimidine, benzodiazepine, and benzothiazepine rings through their corresponding oxoketene dithioacetal derivatives 6 and 7, respectively.