Chemistry of Natural Compounds

, Volume 7, Issue 4, pp 460–465 | Cite as

Synthesis of 4-alkyl-substituted derivatives of cycloserine

  • I. Teplan
  • I. Mezö
  • G. Vegh
  • A. B. Silaev


  1. 1.

    A method for the synthesis of 4-isobutylcycloserine (4-amino-4-isobutyl-3-oxazolidone) has been developed.

  2. 2.

    4-Methyl-, 4-propyl-, and 4-isobutyloxazoline-4-carbohydroxamic acids have been obtained from the corresponding α-alkylserines.



Hydroxamic Acid Sodium Methoxide Thionyl Chloride Hydroxylamine Hydrochloride Absolute Methanol 


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Literature cited

  1. 1.
    I. Teplan, I. Mezö, and G. Vegh, Vegyeszkongresszus, Sopron (1965).Google Scholar
  2. 2.
    D. A. Harris, M. Ruger, M. A. Reagen, F. J. Wolf, R. L. Peck, H. Wallich, and H. B. Woodruff, Antibiotics and Chemotherapy,5, 183 (1955).PubMedGoogle Scholar
  3. 3.
    R. L. Harnea, P. H. Hidy, and E. K. La Baw, Antibiotics and Chemotherapy,5, 204 (1955).Google Scholar
  4. 4.
    R. P. Buks, I. Putter, R. Ormond, J. E. Lyons, L. Chaiet, F. A. Kuehl Jr., F. J. Wolf, N. R. Trenner, R. L. Peck, E. House, G. Downing, E. Newstand, and F. Folkers, J. Amer. Chem. Soc.,77, 2344 (1955).Google Scholar
  5. 5.
    P. H. Hidy, E. B. Hodge, V. V. Young, R. L. Harned, G. A. Brewer, W. F. Phillips, F. W. Runge, H. E. Stovely, A. Pokland, H. Boat, and H. R. Sullivan, J. Amer. Chem. Soc.,77, 2345 (1955).CrossRefGoogle Scholar
  6. 6.
    Ch. H. Stammer, A. N. Wilson, F. W. Holly, and K. Folkers, J. Amer. Chem. Soc.,77, 2346 (1955).CrossRefGoogle Scholar
  7. 7.
    Pl. A. Plattner, A. Boller, H. Frick, A. Fürst, B. Hegedüs, H. Kirchensteiner, St. Majnoni, R. Schläpfer, and N. Spiegejberg, Helv. Chim. Acta,40, 1531 (1957).CrossRefGoogle Scholar
  8. 8.
    Ch. H. Stammer, A. N. Wilson, C. F. Spencer, F. W. Bachelor, F. W. Holly, and K. Folkers, J. Amer. Chem. Soc.,79, 3236 (1957).CrossRefGoogle Scholar
  9. 9.
    U. S. Patent No. 2,772,281; Chem. Abstr.,51, 8145 (1957).Google Scholar
  10. 10.
    N. K. Kochetkov, É. I. Budovskii, R. M. Khomutov, and M. Ya. Karpeiskii, Zh. Obschch. Khim.,29, 635 (1959).Google Scholar
  11. 11.
    R. M. Khomutov, M. Ya. Karpeiskii, É. I. Budovskii, E. S. Severin, and N. K. Kochetkov, Zh. Obshch. Khim.,29, 1328 (1959).Google Scholar
  12. 12.
    U. S. Patent No. 2,842,565; Chem. Abstr.,53, 4302 (1959).Google Scholar
  13. 13.
    U. S. Patent No. 2,918,472; Chem. Abstr.,54, 13, 146 (1960).Google Scholar
  14. 14.
    U. S. Patent No. 2,929,836; Chem. Abstr.,54, 13, 146 (1960).Google Scholar
  15. 15.
    U. S. Patent No. 2,939,868; Chem. Abstr.,54, 22, 683 (1960).Google Scholar
  16. 16.
    T. Tanaka and N. Sugimoto, Yakugaku Kenkyu,33, 428 (1961); Chem. Abstr.,55, 25952 (1961).Google Scholar
  17. 17.
    K. Hayashi, C. G. Skinner, and W. Shive, J. Org. Chem.,26, 1167 (1961).CrossRefGoogle Scholar
  18. 18.
    I. Teplan, B. Tanacs, G. Vegh, and J. Marton, Vegyeszkonferencia, Sseged (1963).Google Scholar
  19. 19.
    B. Tanacs, I. Teplan, and J. Marton, XIXth Int. Cong. of Pure and Appl. Chem. (IUPAC), London (1963).Google Scholar
  20. 20.
    I. Teplan, B. Tanacs, I. Marton, G. Vegh, and A. B. Silaev, in the Zh. Obshch. Khim. collection: Synthesis of Natural Compounds and Their Analogs and Fragments [in Russian], Moscow (1965), p. 169.Google Scholar
  21. 21.
    E. M. Fry, J. Org. Chem.,14, 887 (1949).CrossRefGoogle Scholar
  22. 22.
    E. M. Fry, J. Org. Chem.,15, 438, 802 (1950).CrossRefGoogle Scholar
  23. 23.
    J. H. Billman and E. E. Parker, J. Amer. Chem. Soc.,67, 1069 (1945).CrossRefGoogle Scholar
  24. 24.
    R. Ratonics and R. Behar, Bull. Soc. Chim. Fr.,1957, 1255.Google Scholar
  25. 25.
    L. R. Jones, Anal. Chem.,28, 39 (1956).CrossRefGoogle Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • I. Teplan
  • I. Mezö
  • G. Vegh
  • A. B. Silaev

There are no affiliations available

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