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Chemistry of Natural Compounds

, Volume 12, Issue 3, pp 294–301 | Cite as

The structure of nitrarine

  • S. -M. Nasirov
  • A. A. Ibragimov
  • V. G. Andrianov
  • S. Kh. Maekh
  • Yu. T. Struchkov
  • S. Yu. Yunusov
Article

Summary

Dehydrogenation of the alkaloid nitrarine with selenium has given 3-(quinolin-8′-yl)-β-carboline (II) and 3-(5′, 6′, 7′, 8′-tetrahydroquinolin-8′-yl)-β-carboline (III).

On the basis of the results of a study of the chemical and physical properties of nitrarine, and also from the results of x-ray structural analysis, structure (I) has been established for it.

Keywords

Selenium Alkaloid Yohimbine Boat Conformation Quinolizidine 

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Literature cited

  1. 1.
    A. A. Ibragimov, S.-M. Nasirov, V. G. Andrianov, S. Kh. Maekh, Yu. T. Struchkov, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 273 (1975).Google Scholar
  2. 2.
    A. W. Sangster and K. L. Stuart, Chem. Rev.,65, 69 (1965).CrossRefGoogle Scholar
  3. 3.
    L. D. Antonaccio et al., J. Am. Chem. Soc.,89, 2161 (1962).CrossRefGoogle Scholar
  4. 4.
    J. Beynon, Mass Spectrometry and Its Applications to Organic Chemistry, Elsevier, Amsterdam (1960).Google Scholar
  5. 5.
    K. Horvath-Dara and O. Clauder, Acta Chim. Acad. Sci. Hungaricae,84, 93 (1975).Google Scholar
  6. 6.
    I. Nimomiya and T. Natto, Heterocycles,2, 607 (1974); Chem. Abstr.,82, No. 5, 510 (1975).CrossRefGoogle Scholar
  7. 7.
    I. Ninomiya, H. Takasugi, and T. Naito, Chem. Comm., 732 (1973).Google Scholar
  8. 8.
    H. Bickel, H. Schmid, and P. Karrer, Helv. Chim. Acta,38, 649 (1955).CrossRefGoogle Scholar
  9. 9.
    E. Godar and R. P. Mariella, J. Am. Chem. Soc.,79, 1402 (1957).CrossRefGoogle Scholar
  10. 10.
    O. E. Edwards and N. F. Elmore, Canad. J. Chem.,10, 256 (1962).CrossRefGoogle Scholar
  11. 11.
    P. Karrer, R. Schwyzer, A. Flam, and R. Saemann, Helv. Chim. Acta,35, 865 (1952).CrossRefGoogle Scholar
  12. 12.
    J. D. Spenser, J. Chem. Soc., 3659 (1956).CrossRefGoogle Scholar
  13. 13.
    J. P. Fennessey and W. Nowacki, Z. Kristallogr.,131, 342 (1971).CrossRefGoogle Scholar
  14. 14.
    G. Ambady and G. Gartha, J. Cryst. Mol. Struct.,3, 37 (1973).CrossRefGoogle Scholar
  15. 15.
    N. Finch, C. W. Gemenden, et al., J. Am. Chem. Soc.,87, 2229 (1965).CrossRefGoogle Scholar
  16. 16.
    J. Karle and I. Karle, Acta Crystallogr.,B24, 81 (1968).CrossRefGoogle Scholar
  17. 17.
    A. N. Chekhlov, Z. Kaluski, Yu. T. Struchkov, et al., Zh. Strukt. Khim.,15, 886 (1974).Google Scholar
  18. 18.
    G. I. Birnbaum, Acta Crystallogr.,B26, 755 (1970).CrossRefGoogle Scholar
  19. 19.
    P. N. Edwards and G. F. Smith, Proc. Chem. Soc., 215 (1960).Google Scholar
  20. 20.
    G. M. Badger et al., J. Chem. Soc., 867 (1950).Google Scholar
  21. 21.
    H. Kny and B. Witkop, J. Org. Chem.,25, 635 (1960).CrossRefGoogle Scholar
  22. 22.
    C. Djerassi et al., Experientia,17, 162 (1961).CrossRefGoogle Scholar
  23. 23.
    C. Djerassi, A. A. P. G. Archer, et al., Tetrahedron,16, 212 (1961).CrossRefGoogle Scholar
  24. 24.
    G. F. Smith and J. T. Wrobel, J. Chem. Soc., 1464 (1960).Google Scholar
  25. 25.
    E. Wenkert, J. Am. Chem. Soc.,84, 98 (1962).CrossRefGoogle Scholar
  26. 26.
    Tables of Interatomic Distances and Configuration in Molecules and Ions, The Chemical Society, London (1965); Supplement (1956–1959).Google Scholar
  27. 27.
    G. L. Birnbaum, Acta Crystallogr.,23, 526 (1967).CrossRefGoogle Scholar
  28. 28.
    S.-M. Nasirov, V. G. Andrianov, Yu. T. Struchkov, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 197 (1976).Google Scholar
  29. 29.
    S.-M. Nasirov, V. G. Andrianov, Yu. T. Struchkov, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 206 (1976).Google Scholar
  30. 30.
    W. C. Hamilton and J. A. Ibers, Hydrogen Bonding in Solids, Benjamin, New York (1968).Google Scholar
  31. 31.
    N. G. Bokii, Yu. T. Struchkov, D. N. Kravtsov, and E. M. Rokhlina, Zh. Strukt. Khim.,14, 291 (1973).Google Scholar
  32. 32.
    V. I. Andrianov, B. L. Tarnopol'skii, and Z. Sh. Safina, Rentgen 70, an Automated System of Programs for X-Ray Structural Calculations [in Russian], OIKhF AN SSSR, Moscow (1972).Google Scholar
  33. 33.
    A. N. Chekhlov, Yu. T. Struchkov, and A. I. Kitaigorodskii, Zh. Strukt. Khim.,15, 754 (1974).Google Scholar
  34. 34.
    H. P. Hanson, F. Herman, J. D. Lea, and S. Skillman, Acta Crystallogr.,17, 1040 (1964).CrossRefGoogle Scholar
  35. 35.
    D. T. Cromer and D. Liberman, J. Chem. Phys.,53, 1891 (1970).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • S. -M. Nasirov
  • A. A. Ibragimov
  • V. G. Andrianov
  • S. Kh. Maekh
  • Yu. T. Struchkov
  • S. Yu. Yunusov

There are no affiliations available

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