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 a 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 intermediate 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.

Acid Catalysed Rearrangements in the Aryliminoindoline Series. Part 4. Reactions of 1,2-Dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3-phenylimino-3H-indole with Trichloro acetic and Hydrochloric Acids. Crystal Structure of 1,2-Dihydro-2-phenyl-2-(indol-3-yl)-3-phenilimino-3H-indole / B., Cardillo; C., Conti; E., Giorgini; L., Greci; P., Stipa; G., Tosi; Rizzoli, Corrado; Sgarabotto, Paolo; Ugozzoli, Franco. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 29:(1992), pp. 1349-1355. [10.1002/jhet.5570290550]

Acid Catalysed Rearrangements in the Aryliminoindoline Series. Part 4. Reactions of 1,2-Dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3-phenylimino-3H-indole with Trichloro acetic and Hydrochloric Acids. Crystal Structure of 1,2-Dihydro-2-phenyl-2-(indol-3-yl)-3-phenilimino-3H-indole

RIZZOLI, Corrado;SGARABOTTO, Paolo;UGOZZOLI, Franco
1992

Abstract

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 a 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 intermediate 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.
Acid Catalysed Rearrangements in the Aryliminoindoline Series. Part 4. Reactions of 1,2-Dihydro-2-phenyl-2-(indol-3-yl-derivatives)-3-phenylimino-3H-indole with Trichloro acetic and Hydrochloric Acids. Crystal Structure of 1,2-Dihydro-2-phenyl-2-(indol-3-yl)-3-phenilimino-3H-indole / B., Cardillo; C., Conti; E., Giorgini; L., Greci; P., Stipa; G., Tosi; Rizzoli, Corrado; Sgarabotto, Paolo; Ugozzoli, Franco. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 29:(1992), pp. 1349-1355. [10.1002/jhet.5570290550]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2313517
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