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Synthesis of isoxazolidine derivatives from N-substituted hydroxylamines and α,Β-unsaturated ketones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of methyl vinyl ketone with N-Phenyl-hydroxylamine leads to a tautomeric mixture of 5-hydroxy-2-phenyl-5-methylisoxazolidine and its linear form, while the reaction with benzohydroxamic acid leads to linear products of addition to the oxygen or nitrogen atoms, depending on the reaction conditions. The first representatives of 5-hydroxyisoxazolidines with the residue of an aliphatic carboxylic acid attached to the nitrogen atom were obtained by acylation of 5-hydroxy-3,3,5-trimethylisoxazolidine.

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Literature Cited

  1. K. Torssell and O. Zeuthen, Acta Chem. Scand., 32, 118 (1978).

    Google Scholar 

  2. K. N. Zelenin, I. A. Motorina, L. A. Sviridova, I. P. Bezhan, A. Yu. Ershov, G. A. Golubeva, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 9, 1270 (1987).

    Google Scholar 

  3. B. Monzyx and A. L. Crumbliss, J. Am. Chem. Soc., 101, 6203 (1979).

    Google Scholar 

  4. W. Kliegel and D. Nanninga, Chem. Ber., 116, No. 7, 2616 (1983).

    Google Scholar 

  5. I. A. Motorina, L. A. Sviridova, G. A. Golubeva, K. N. Zelenin, I. P. Bezhan, A. Yu. Ershov, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 12, 1661 (1988).

    Google Scholar 

  6. A. Belly, R. Jacquier, F. Petrus, and J. Verducci, Bull. Soc. Chim. France, No. 1, (1972).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 823–826, June, 1989.

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Bezhan, I.P., Zelenin, K.N., Sviridova, L.A. et al. Synthesis of isoxazolidine derivatives from N-substituted hydroxylamines and α,Β-unsaturated ketones. Chem Heterocycl Compd 25, 684–687 (1989). https://doi.org/10.1007/BF00470030

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  • DOI: https://doi.org/10.1007/BF00470030

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