Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 4, Issue 17, Pages 3282-3290Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b607680g
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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.
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