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Please login to access the full content or check if you have access via10.15.1.1.4.5.2 Method 2: Synthesis of 2-(2-Aminoethyl)carbazoles
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Gallagher, P. T., Science of Synthesis, (2001) 10, 706.
1H-Indole (50) reacts with ketals derived from 4-acetylpyridine to produce (aminoethyl)carbazoles (Scheme 22).[71] Thus, 4-acetyl-1-methyl-1,2,5,6-tetrahydropyridine ethylene glycol ketal (51) reacts with indole in aqueous acetic acid during extended reflux. Under the conditions of the reaction the ketal deprotects and isomerizes to a 3,4,5,6-tetrahydropyridine, which is electrophilic towards indole in the 3-position. The intermediate tetrahydrocarbazole aromatizes with loss of water to produce 1-methyl-2-(2-methylamino)ethyl-9H-carbazole (52) in 74% yield. This reaction has also been reported with 1,4-diacylpiperidines and forms carbazoles in modest yields.[72]
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References
| [71] | Meeeeeeeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [72] | Meeee, M.; Meee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 88. |
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