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

Abstract

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, 2-b]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.