Journal of Organic Chemistry p. 6764 - 6770 (1995)
Update date:2022-09-26
Topics:
Chiba, Toshiro
Sakagami, Hirotoshi
Murata, Miki
Okimoto, Mitsuhiro
The indirect electrooxidation of ketones in ammoniacal methanol using iodide ion as a mediator afforded 2,2-dialkyl-2,5-dihydro-1H-imidazoles 3 via an oxidative cyclocoupling of ketimine intermediates formed from ketones and ammonia.The treatment of 3 with dilute HCl gave α-amino ketone hydrochlorides 4 and the parent ketones in good yields.A similar electrooxidation of 3 resulted in the formation of the corresponding 2H-imidazoles 6, which were hydrolyzed to α-diketones and the parent ketones.The same products 6 could also conveniently be obtained by chemical oxidation of 3 with aqueous NaOCl.
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