OXIDATION AND REDUCTION OF SUBSTITUTED 4-HYDROXYAMINO AND 4-OXIMINOIMIDAZOLIDIN-2-ONES

Article abstract of DOI:10.1007/BF00506887

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.