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Synthesis and properties of carbamoyl derivatives of 5-hydroxy-3,3,5-trimethylisoxazolidine

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 5-hydroxy-3,3,5-trimethylisoxazolidine with alkyl (or aryl) isocyanates gives N-alkyl(aryl)-carbamoyl-5-hydroxy-3,3,5-trimethylisoxazolidines, which react with methanol in the presence of p-toluenesulfonic acid to give 5-methoxy-1-carbamoyl derivatives of isoxazolidine. When arylcarbamoyl-5-hydroxy-3,3,5-trimethylisoxazolidines are heated in carbon tetrachloride, they are converted to O-arylcarbamoyl-N-(2-methyl-4-oxo-2-pentyl)hydroxylamines, the treatment of which with hydrogen chloride in benzene made it possible to isolate 1,2,6-oxadiazepin-7-ones along with the hydrochloride of the given compounds.

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Authors and Affiliations

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

    A. F. Rukasov, V. P. Tashchi, Yu. A. Kondrat'ev, Yu. A. Baskakov & Yu. G. Putsykin

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  1. A. F. Rukasov
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  2. V. P. Tashchi
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  3. Yu. A. Kondrat'ev
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  4. Yu. A. Baskakov
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  5. Yu. G. Putsykin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 746–750, June, 1979.

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Rukasov, A.F., Tashchi, V.P., Kondrat'ev, Y.A. et al. Synthesis and properties of carbamoyl derivatives of 5-hydroxy-3,3,5-trimethylisoxazolidine. Chem Heterocycl Compd 15, 603–607 (1979). https://doi.org/10.1007/BF00539492

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  • DOI: https://doi.org/10.1007/BF00539492

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