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Herein, a straightforward facile synthesis of indolo2,3-cquinoline analogues was reported from 2-arylamino(phenylsulfonyl)methylindoles involving PIDA/BF3·OEt2-mediated intramolecular dehydrogenative coupling (IDC) as a key step. Even though isomeric 3-arylamino(phenylsulfonyl)methylindoles, upon interaction with PIDA/BF3·OEt2, led to complications, synthesis of the indolo3,2-cquinoline framework could be easily achieved from N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamide by employing a Pd(0)-mediated intramolecular cyclization reaction. Under identical conditions, synthesis of indolo2,3-cquinolines was also accomplished from the respective N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamides. The SRB assay of fluorine-bound indoloquinolines displayed nanomolar-level cytotoxicity against a nonsmall lung cancer cell line, NCI-H460.
Pavunkumar et al. (Fri,) studied this question.