OXIDATION AND REDUCTION OF SUBSTITUTED 4-HYDROXYAMINO AND 4-OXIMINOIMIDAZOLIDIN-2-ONES
4-Oximino-3-aryl(alkyl)-5,5-dimethylimidazolidin-2-ones were obtained by air oxidation of substituted 4-hydroxyaminoimidazolidin-2-ones in the presence of sodium ethoxide.In hydrochloric acid 4-oximino-3-(3',4'-dichlorophenyl)imidazolidin-2-one gives the corresponding hydantoin, whereas 4-oximino-3-(1'-phenylethyl)imidazolidin-2-one gives its E isomer with respect to the oxime group.The reduction of 4-oximino-3-alkylimidazolidin-2-ones with Raney alloy in 20percent NaOH or hydrogenation on a palladium catalyst leads to 4-imino derivatives, whereas reduction of 4-oximino-3-aryl-5,5-dimethylimidazolidin-2-ones that contain chlorine atoms in their aromatic rings with sodium in liquid ammonia leads to their dehalogenation.
Epshtein, S. P.,Rukasov, A. F.,Tashchi, V. P.,Simonova, T. G.,Putsykin, Yu. G.
p. 993 - 996
(2007/10/02)
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