Skip to main content
SpringerLink
Log in

13C and1H NMR spectra of spiropiperidine alkaloids of Nitraria

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

A detailed interpretation is given of the13C and1H NMR spectroscopy of the spiropiperidine alkaloids of the nitramine group, and the results are generalized. The assignment has been made of the carbon-13 resonance lines in the spectra of five natural compounds. A dependence of the parameters on the spatial structures of the compounds of this series has been found. The overall PMR spectra of seven natural alkaloids and some of their derivatives are discussed. The conformations of acyl derivatives have been established.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Chemists, Wiley, New York (1972).

    Google Scholar 

  2. H. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York (1972).

    Google Scholar 

  3. A. A. Ibragimov, Z. Osmanov, B. Tashkhodzhaev, N. D. Abdullaev, M. R. Yagudaev, and S. Yu. Yunusov, Khim. Prir. Soedin., 623 (1981).

  4. A. A. Ibragimov, G. P. Moiseeva, Z. Osmanov, and S. Yu. Yunusov, Khim. Prir. Soedin., 726 (1986).

  5. D. M. Grant and B. V. Cheny, J. Am. Chem. Soc.,89, 5315 (1967).

    Google Scholar 

  6. H.-J. Schneider and W. Freitag, Chem. Ber.,112, 16 (1979).

    Google Scholar 

  7. L. F. Johnson and W. C. Jankowski, Carbon-13 NMR Spectra, Wiley-Interscience, New York (1972).

    Google Scholar 

  8. D. Zimmerman, R. Ottinger, J. Reisse, H. Christol, and J. Brugidou, Org. Magn. Res.,6, 346 (1974).

    Google Scholar 

  9. S. H. Grover, J. P. Guthrie, J. B. Stothers, and C. T. Tan, J. Magn. Res.,10, 227 (1973).

    Google Scholar 

  10. E. L. Eliel, W. F. Bailey, L. D. Kopp, R. L. Willer, D. M. Grant, R. Bertrand, K. A. Christensen, D. K. Dalling, M. W. Duch, E. Wenkert, F. M. Schell, and D. W. Cochran, J. Am. Chem. Soc.,97, 322 (1975).

    Google Scholar 

  11. H. Zondler and W. Pfleiderer, Helv. Chim. Acta,58, 2247 (1975).

    Google Scholar 

  12. D. G. Hawthorne, S. R. Johns, and R. I. Willing, Aust. J. Chem.,29, 315 (1976).

    Google Scholar 

  13. H. Booth and D. V. Griffiths, J. Chem. Soc., Perkin Trans. II, 842 (1973); T. A. Crabb and P. A. Jupp, J. Chem. Soc., Perkin Trans. I, 913 (1985).

  14. Yu. Yu. Samitov, O. I. Danilova, B. V. Unkovsky, and I. P. Boiko, Magn. Res. Chem.,24, 480 (1986).

    Google Scholar 

  15. N. S. Zefirov, Usp. Khim.,44, 413 (1975).

    Google Scholar 

  16. A. A. Ibragimov and S. Yu. Yunusov, Khim. Prir. Soedin., 730 (1986).

  17. B. Tashkhodzhaev, A. A. Ibragimov, and S. Yu. Yunusov, Khim. Prir. Soedin., 692 (1985).

  18. N. Takaishi, I. Inamoto, and K. Aigami, J. Org. Chem.,40, 276 (1975).

    Google Scholar 

  19. J. R. Wiseman and H. O. Krabbenhoft, J. Org. Chem.,40, 3222 (1975).

    Google Scholar 

  20. A. Heumann and K. Kolshorn, Tetrahedron,31, 1571 (1975).

    Google Scholar 

  21. H. J. Schneider, M. Lonsdorfer, and E. F. Weigand, Org. Magn. Res.,8, 363 (1976).

    Google Scholar 

  22. J. D. Roberts, F. J. Weigert, J. L. Kroschwitz, and H. J. Reich, J. Am. Chem. Soc.,92, 1338 (1970).

    Google Scholar 

  23. T. Penk, E. Lippmaa, V. V. Sevostjanova, M. M. Krayuschkin, and A. I. Tarasova, Org. Magn. Res.,3, 783 (1971); G. E. Maciel, H. C. Dorn, R. L. Greene, W. A. Kleschick, M. R. Peterson, Jr., and G. H. Wahl, Jr., Org. Magn. Res.,6, 178 (1974); G. E. Maciel and H. C. Dorn, J. Am. Chem. Soc.,93, 1268 (1971).

    Google Scholar 

  24. A. A. Ibragimov, N. D. Abdullaev, Z. Osmanov, and S. Yu. Yunusov, Khim. Prir. Soedin., 685 (1987).

  25. F. G. Riddel and J. M. Lehn, J. Chem. Soc. (B), 1224 (1968).

  26. P. Sohar, F. Fülop, and G. Bernath, Org. Mag. Res.,22, 527 (1984).

    Google Scholar 

  27. M. Schamma and D. M. Hindenlang, Carbon-13 NMR Shift Assignments of Amines and Alkaloids, Plenum, New York (1979); E. Röder, H. Wiedenfeld, and A. Hoenig, Planta Med., 164 (1985); M. R. Roby and F. R. Stermitz, J. Nat. Prod.,47, 846 (1984).

    Google Scholar 

  28. R. Verpoote, P. J. Hylands, and N. G. Bisset, Org. Magn. Res.,9, 567 (1977).

    Google Scholar 

  29. A. A. Ibragimov, Z. Osmanov, M. R. Yagudaev, and S. Yu. Yunusov, Khim. Prir. Soedin., 213 (1983).

  30. H. Booth and H. Bostock, J. Chem. Soc. Chem. Commun., 637 (1967); H. Zondler and W. Pfleiderer, Ann. Chem.,759, 84 (1972); T. P. Forrest and S. Ray, J. Chem. Soc. Chem. Commun., 1537 (1970); D. Wendisch et al., Org. Magn. Res. Spectral Suppl.,4, No. 3, 0485–0488 (1972).

  31. H. Booth and A. H. Bostock, J. Chem. Soc. Perkin Trans. II, 615 (1972).

  32. T. A. Crabb, Annu. Rep. NMR Spectroscopy,6, 250–387 (1975).

    Google Scholar 

  33. C. C. Ramey, D. C. Lini, and G. Krow, Annu. Rep. NMR Spectroscopy, 6A, 148–248 (1975); D. H. Rele, H. H. Mathur, G. Trivedi, and K. V. R. Chary, Magn. Res. Chem.,24, 687 (1986).

    Google Scholar 

  34. Z. Osmanov, A. A. Ibragimov, and S. Yu. Yunusov, Khim. Prir. Soedin., 225 (1982).

  35. P. W. Jeffs, R. L. Hawks, and D. S. Farrier, J. Am. Chem. Soc.,91, 3831 (1969).

    Google Scholar 

  36. J. B. Lambert, D. S. Bailey, and B. F. Michel, Tetrahedron Lett., 691 (1970).

  37. A. A. Ibragimov and S. Yu. Yunusov, Khim. Prir. Soedin., 655 (1986).

  38. Yu. E. Kazantsev, I. P. Boiko, Yu. F. Malina, O. I. Zhuk, Yu. Yu. Samitov, and B. V. Unkovskii, Zh. Org. Khim.,9, 2597 (1973).

    Google Scholar 

  39. D. M. Lynch and W. Cole, J. Org. Chem.,31, 3337 (1966).

    Google Scholar 

  40. H. O. House, B. A. Tefertiller, and C. G. Pitt, J. Org. Chem.,31, 1073 (1966).

    Google Scholar 

Download references

Authors
  1. A. A. Ibragimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Yu. Yunusov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 82–91, January–February, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ibragimov, A.A., Yunusov, S.Y. 13C and1H NMR spectra of spiropiperidine alkaloids of Nitraria. Chem Nat Compd 24, 71–78 (1988). https://doi.org/10.1007/BF00597578

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00597578

Keywords

Search

Navigation