Summary
1. It has been shown that in the chemical reactions for obtaining the N-oxides of lupinine and tropine the bicyclic systems of quinolizidine and tropane exhibit a conformational lability due to inversion.
2. On the basis of IR and PMR spectra the structure and conformation of the isomeric N-oxides of lupinine and tropine have been determined.
Similar content being viewed by others
Literature cited
F. Galinovsky and H. Nesbadba, Monatsh. Chem.,85, 1300 (1954).
G. Fodor, J. Toth, and J. Vincze, J. Chem. Soc.,1955, 3504; G. Fodor, and O. Kovacs, J. Chem. Soc.,1953, 724.
E. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill (1962).
T. K. Yunusov, A. I. Ishbaev, V. B. Leont'ev, and A. S. Sadykov, Khim. Prirodn. Soedin., 49 (1971).
G. Closs, J. Amer. Chem. Soc.,81, 5456 (1959).
Additional information
V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 477–483, July–August, 1972.
Rights and permissions
About this article
Cite this article
Yunusov, T.K., Leont'ev, V.B., Kamaev, F.G. et al. Conformational transformations of the alkaloids lupinine and tropine on the formation of their N-oxides. Chem Nat Compd 8, 473–477 (1972). https://doi.org/10.1007/BF00563672
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00563672