Issue 17, 2006

Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent

Abstract

The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2–CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted with nitrous acid, 1-methyl-2-phenylindole gives also the corresponding azo-bis-indole in good yields. The reaction of indole with nitrogen dioxide leads to 2-(indol-3-yl)-3H-indol-3-one as the main product together with small amounts of 2-(indol-3-yl)-3H-indol-3-oxime; whereas the major product obtained when the same indole is reacted with nitrous acid is represented by 2-(indol-3-yl)-3H-indol-3-oxime. The reaction of 3-alkyl substituted indoles with nitrogen dioxide is rather complex and results in the formation of different nitro indoles, whereas nitrosation is observed when nitrous acid is used. Crystal structures of 2-(indol-3-yl)-3H-indol-3-one and of 4-nitro-N-acetyltryptamine have been determined by X-ray analysis.

Graphical abstract: Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent

Article information

Article type
Paper
Submitted
30 May 2006
Accepted
05 Jul 2006
First published
26 Jul 2006

Org. Biomol. Chem., 2006,4, 3282-3290

Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent

P. Astolfi, M. Panagiotaki, C. Rizzoli and L. Greci, Org. Biomol. Chem., 2006, 4, 3282 DOI: 10.1039/B607680G

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