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A number of 5,11-dialkyl-6,12-di(hetero)aryl-5,11-dyhydroindolo[3,2-b]carbazoles has been synthesized by modified method based on HBr catalyzed condensation of (hetero)aromatic aldehydes with indole in MeCN solution affording 5,6,11,12-tetrahydroindolo[3,2-b]carbazoles, that have been aromatized with I2 in DMF solution for 1 h at reflux, followed by alkylation of 5,11-dihydro compounds. New 2,8-dicyano(10 examples) as well as 2,8-bis(benzo[d]thiazol-2-yl)-substituted (5 examples) derivatives of these 5,11-dyhydroindolo[3,2b]carbazoles have been obtained through their initial C2,8-formylation, followed by treatment of dialdehydes with excess of hydroxylamine and dehydration of the formed aldoximes with acetic anhydride or by interaction with excess of 2-aminothiophenol in DMSO solution, respectively.

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An improved protocol for the preparation of 5,11-dialkyl-6,12-di(hetero)aryl-5,11-dihydroindolo[3,2-b]carbazoles and synthesis of their new 2,8-dicyano- / 2,8-bis(benzo[d]thiazol-2-yl)-substituted derivatives