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Oxidation and reduction of substituted 4-hydroxyamino- and 4-oximinoimidazolidin-2-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4-Oximino-3-aryl(alkyl)-5,5-dimethylimidazolidin-2-ones were obtained by air oxidation of substituted 4-hydroxyaminoimidazolidir-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 20% 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.

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Authors and Affiliations

  1. All-Union Scientific-Research Institute of Chemical Agents for the Protection of Plants, 109088, Moscow

    S. P. Épshtein, A. F. Rukasov, V. P. Tashchi, T. G. Simonova & Yu. G. Putsykin

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  1. S. P. Épshtein
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  2. A. F. Rukasov
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  3. V. P. Tashchi
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  4. T. G. Simonova
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  5. Yu. G. Putsykin
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1240–1243, September, 1983.

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Épshtein, S.P., Rukasov, A.F., Tashchi, V.P. et al. Oxidation and reduction of substituted 4-hydroxyamino- and 4-oximinoimidazolidin-2-ones. Chem Heterocycl Compd 19, 993–996 (1983). https://doi.org/10.1007/BF00506887

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  • DOI: https://doi.org/10.1007/BF00506887

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