Chemistry of Natural Compounds

, Volume 9, Issue 2, pp 183–187 | Cite as

Synthesis of some new analogs of argemonine of the type of 4,4,8,8-tetramethyl-2,3;6,7-dibenzo-9-azabicyclo [3.3.1] nonane-1,5-diols

  • R. M. Lagidze
  • N. K. Iremadze
  • M. Sh. Vashakidze
  • B. V. Rozynov


It has been shown that the transannular reaction of the readily available 3,3,7,7-tetramethyl-1,2;5,6-dibenzocyclooctane-4,8-dione with various aliphatic and aliphatic-aromatic primary amines forms good yields of the corresponding 4,4,8,8-tetramethyl-2,3;6,7-dibenzo-9-azabicyclo[3.3.1]nonane-1,5-diols. These compounds have the symmetrical dibenzocyclooctane skeleton with the aza grouping characteristic for argemonine and alkaloids related to it.


Diol Acetic Anhydride Show Absorption Band Hexamethylenediamine White Crystalline Substance 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    R. M. Lagidze, N. K. Iremadze, and G. G. Samsoniya, Soobshch. Akad. Nauk GruzSSR,17, No. 2, 309 (1967).Google Scholar
  2. 2.
    R. M. Lagidze, N. K. Iremadze, and M. Sh. Vashakidze, Zh. Organ. Khim.,4, 2006 (1968).Google Scholar
  3. 3.
    R. M. Lagidze, N. K. Iremadze, and M. Sh. Vashakidze, 3rd International Congress on Heterocyclic Chemistry, Sendai, Japan, August 23–27, 1971.Google Scholar
  4. 4.
    M. J. Martell, J. T. O. Soine, and Lemonet B. Kier, J. Amer. Chem. Soc.,85, 1022 (1963).CrossRefGoogle Scholar
  5. 5.
    F. R. Stermitz and M. Seiber, J. Org. Chem.,31, 2925 (1966).CrossRefGoogle Scholar
  6. 6.
    A. C. Barker and A. R. Battersby, J. Chem. Soc., 1317 (1967).Google Scholar
  7. 7.
    L. Bellamy, Infra-red Spectra of Complex Molecules, Methuen (1958).Google Scholar
  8. 8.
    J. R. Dyer, Applications of the Absorption Spectroscopy of Organic Compounds, Prentice-Hall, Englewood Cliffs, New Jersey (1965).Google Scholar
  9. 9.
    R. M. Lagidze, I. G. Abesadze, et al., Trudy Gruz. In-ta Subtropich. Khozyaistva, Sukhumi,14, 597 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • R. M. Lagidze
  • N. K. Iremadze
  • M. Sh. Vashakidze
  • B. V. Rozynov

There are no affiliations available

Personalised recommendations