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Direct Amination. Part 2. Reaction Of 2-phenylindole With Primary Aromatic Amines. A Chemical And Electrochemical Investigation

C. Berti, L. Greci, R. Andruzzi, A. Trazza
Published 1986 · Chemistry

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The reaction of 2-phenylindole with primary aromatic amines to form 2-phenyl-3-arylimino-3H-indoles, in the presence of N-chlorobenzotriazole, N-chloroisatin or lead tetra-acetate, were also investigated by anodic oxidation. The chemical and electrochemical results suggest a mechanism involving an intermediate nitrenium ion, whose formation was demonstrated by an independent route. The reaction of 1-hydroxy-2-phenylindole with p-anisidine to form 2-phenyl-3-p-methoxyphenylimino-3H-indole 1-oxide, previously studied under anodic oxidation is here described in the presence of N-chlorobenzotriazole.

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