Chemistry of Natural Compounds

, Volume 8, Issue 3, pp 322–326 | Cite as

An investigation of quinolizidine alkaloids by the optical rotatory dispersion (ORD) method

I. ORD of alkaloids of the lupinine, cytisine, sparteine, and aphyllinic acid group
  • A. I. Ishbaev
  • Kh. A. Aslanov
  • A. S. Sadykov
  • M. A. Ramazanova


1. The ORD curves of alkaloids of the sparteine, lupinine, and cytisine groups and of some derivatives of aphyllinic acid have been investigated. In the compounds investigated with an α-pyridone ring the epimers with the trans-quinolizidine linkage of the nuclei have a greater molecular amplitude than the corresponding cis isomers.

2. It has been shown that the alkaloids with a lactam group in an outer ring have higher molecular amplitudes than the corresponding compounds with the >N—C=O group in an inner ring. A dependence of the shape, sign, and molecular amplitude of the curves on the type of linkage of the quinolizidine nuclei and also a dependence of the molecular rotation of the position of a double bond in ring A or D have been given.

3. Derivatives of lupinine and of aphyllinic acid are characterized by curves approximating to a smooth shape with low-intensity anomalies, and in the case of the derivatives of aphyllinic acid studied they are shifted in the long-wave direction.


Cytisine Molecular Rotation Sparteine Quinolizidine Lupinine 


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Literature cited

  1. 1.
    S. Iskandarov and S. Yunusov. Khim. Prirodn. Soedin., 494 (1970).Google Scholar
  2. 2.
    J. Skolik and M. Wiewiorowsky, Bull. Acad. Polon. Sci., Ser. Sci. Chim.,17, 201 (1969).Google Scholar
  3. 3.
    C. Djerassi, Optical Rotatory Dispersion, McGraw-Hill, New York (1960).Google Scholar
  4. 4.
    E. W. Foltz, A. E. Lippman, and C. Djerassi, J. Amer. Chem. Soc.,77, 4359 (1955).CrossRefGoogle Scholar
  5. 5.
    C. Djerassi and W. Closson, J. Amer. Chem. Soc.,78, 3761 (1956).CrossRefGoogle Scholar
  6. 6.
    C. Djerassi, J. Osiecki, and B. Riniker, J. Amer. Chem. Soc.,80, 126 (1958).CrossRefGoogle Scholar
  7. 7.
    G. Snatzke, Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, Heyden and Sons, London (1967).Google Scholar
  8. 8.
    C. Djerassi, R. Records, E. Bunnenberg, K. Mislow, and A. Moscowitz, J. Amer. Chem. Soc.,84, 870 (1962).CrossRefGoogle Scholar
  9. 9.
    C. Y. S. Chen and C. A. Stevenson, J. Phys. Chem.,73, 1642 (1969).CrossRefGoogle Scholar
  10. 10.
    H. E. Zaugg, J. Amer. Chem. Soc.,82, 2903 (1960).CrossRefGoogle Scholar
  11. 11.
    C. Djerassi and W. Closson, J. Amer. Chem. Soc.,81, 4587 (1959).CrossRefGoogle Scholar
  12. 12.
    P. M. Jones and W. Klyne, J. Chem. Soc.,1960, 871.Google Scholar
  13. 13.
    O. Edwards, et al., Can. J. Chem.,32, 235 (1954).CrossRefGoogle Scholar
  14. 14.
    W. Crow, Austr. J. Chem.,12, 474 (1959).CrossRefGoogle Scholar
  15. 15.
    F. Bohlmann, D. Rantz, and C. Arnot, Ber.,91, 2189 (1958).Google Scholar
  16. 16.
    W. Cockburn and L. Marion, Can. J. Chem.,29, 13 (1951).CrossRefGoogle Scholar
  17. 17.
    K. Orazgil'diev, Kh. A. Aslanov, and A. S. Sadykov, Izvestiya AN Turkm SSR, Ser. Fiz. Tekh. i Khim. Nauk,6, 116 (1967).Google Scholar
  18. 18.
    Fam Khoang Nhok, Yu. K. Kushmuradov, Kh. A. Aslanov, and A. S. Sadykov, Trudy TashGU,3, No. 341, 99 (1968).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • A. I. Ishbaev
  • Kh. A. Aslanov
  • A. S. Sadykov
  • M. A. Ramazanova

There are no affiliations available

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