54879-99-1Relevant academic research and scientific papers
Oxidation of 2,3-Disubstituted Indoles with m-Chloroperbenzoic Acid. Formation of o-Aminophenol Derivatives and a Dimeric Product
Hino, Tohru,Yamaguchi, Hitoshi,Matsuki, Kenji,Nakano, Kumiko,Sodeoka, Mikiko,Nakagawa, Masako
, p. 141 - 146 (2007/10/02)
Oxidation of tetrahydrocarbazole (5) with m-chloroperbenzoic acid in methylene dichloride at -60 deg C gave the N-benzoyl-o-aminophenol (11) togehter with the hydroxy-3H-indole (7) and the indol-3(2H)-one (9).The N-benzoyl-o-aminophenol (11) was found to be derived from the hydroxy-4aH-carbazole (7) via an unstable tertiary amine intermediate (17) by further oxidation.The N-benzoyl-o-aminophenol (11) was also obtained by the oxidation of the other hydroxy-3H-indoles (18), (19), and (24).On the other hand, similar oxidation of N-methyl-tetrahydrocarbazole (6) gave the hydroxyenamine (28) and its dimer (27), and of 2,3-diphenylindole (31) and the N-methyl derivative (30) gave the hydroxy-3H-indole (19) and the ketoamide (33), while the 1,4-benzoxazine derivatives (34) and (35) were obtained in the case of the N-acetyl derivative (32).
