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Paper | Regular issue | Vol 34, No. 10, 1992, pp.1917-1926
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6108
Direct Amination. Part 4. Reactions of Indoles with Primary Aromatic Amines and Iodosobenzene Diacetate

Liberato Cardellini, Lucedio Greci,* Eziana Maurelli, Mario Orena, Pierluigi Stipa, and Giorgio Tosi

*Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy


Indole, 2-methylindole, 2-phenylindole, and primary aromatic amines react with iodosobenzene diacetate leading both to 2-arylamino-3-arylimino-3H-indole in the case of indole and 2-methylindole, and to 2-phenyl-3-arylimino-3H-indole in the case of 2-phenylindole. The reaction is believed to proceed through the formation of a nitrenium ion formed by the interaction of iodosobenzene diacetate and primary aromatic amines and the mechanism is supported by experimental evidences. The methyl elimination from 2-methylindole is explained on the basis of the isolation of the possible intermediate and the formation of an aminal, whose decomposition leads to the reaction products. The intermediate aminal is proposed on the basis of the bis-(2-methylindol-3-yl)methane formation.