150057-24-2Relevant articles and documents
Acid Catalyzed Rearrangements in the Arylimino Indoline Series. Part IV. Reactions of 1,2-Dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3-phenylimino-3H-indole with Trichloroacetic and Hydrochloric Acids. Crystal Structure of 1,2-Dihydro-2-phenyl-2-(indol-3-yl)-3-phenylimino-3H-indole
Cardillo, Barbara,Conti, Carla,Giorgini, Elisabetta,Greci, Lucedio,Stipa, Pierluigi,et al.
, p. 1349 - 1355 (2007/10/02)
2-Phenyl-3-phenylimino-3H-indole reacts with indole, 2-methylindole and 1,2-dimethylindole in the presence of stoichiometric trichloroacetic acid to form 1,2-dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3-phenylimino-3H-indole, which during longer period of time (16 hours) undergoes indolyl transposition to carbon-3 and elimination of aniline affording the 3,3'-bis-indolyls.In the case of 1,2-dimethylindole the intermadiate coming from the indolyl migration may undergo a nucleophilic addition to carbon-2 of another molecule of indole; the new intermediate leads to the formation of 2- phenyl-3,3'-di-(1,2-dimethylindol-3-yl)-3H-indole by elimination of aniline and migration to carbon-3 of the second molecule of indole.By treatment with hydrochloric acid in refluxing ethanol, 1,2-dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3-phenylimino-3H-indole afford to 3,3'-bis-indolyls and 1,2-dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3H-indol-3-one (indoxyls).The crystal structure of 1,2-dihydro-2-phenyl-2-(indol-3-yl)-3-phenylimino-3H-indole is also reported.The latter compound does not give rearrangement products by acid treatment, only untreatable tarry material.
