Journal of the Chemical Society. Perkin transactions I p. 290 - 294 (1981)
Update date:2022-09-26
Topics: Heterocyclic compounds Intramolecular Substitution Aromatic nucleophilic Indole derivatives
Kametani, Tetsuji
Ohsawa, Tatsushi
Ihara, Masataka
Cyclisation of N-(2-bromo-4,5-dimethoxyphenethyl)acetamide (6) afforded 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole (13) by intramolecular nucleophilic aromatic substitution using sodium hydride and cuprous halide in dimethylformamide.The dihydroindoles (14), (15), and (16) were also synthesised from the corresponding amides (8) and (10) and the carbamate (12) in a similar manner.The dihydroindoles (13), (14), and (16) were converted into the indoles (20) and (21) in excellent yield by oxidation and subsequent alkaline hydrolysis.The 2-oxindoles (26) and (27) were also prepared under similar reaction condition from the phenylacetamide (24) and (25).
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