Russian Journal of Organic Chemistry

, Volume 44, Issue 11, pp 1665–1670 | Cite as

Synthesis and molecular structure of bis(benzo)aza-14-crown-4 ethers with 7-azabicyclo[3.3.1]nonane and homologous fragments

  • A. N. Levov
  • A. I. Komarov
  • A. T. Soldatenkov
  • G. V. Avramenko
  • S. A. Soldatova
  • V. N. Khrustalev
Article

Abstract

By condensation of cycloalkanes with 2-{2-[2-(2-formylphenoxy)ethoxy]ethoxy}benzaldehyde and ammonium acetate by Petrenko-Kritchenko method first representatives of new heterocyclic systems, bis(benzo)-aza-14-crown-4 ethers containing a 7-aza-bicyclo[3.3.1]nonane or its homologous fragment, were obtained in 6–15% yield. With growing cycle of the initial cycloketone the yield of the azacrownophane considerably grew. By means of XRD analysis the molecular structure was established of four synthesized macrocycles, the relative configuration of asymmetrical atoms was determined, and the size of the internal cavities of the azacrown part was estimated.

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References

  1. 1.
    Levov, A.N., Strokina, V.M., Komarova, A.I., Le Tuan, An’, and Soldatenkov, A.T., Khim. Geterotsikl. Soedin., 2006, p. 139; Levov, A.N., Strokina, V.M., Komarova, A.I., Le Tuan, An’, Soldatenkov, A.T., and Khrustalev, V.N., Mendeleev Commun., 2006, vol. 16, p. 35; Le Tuan, An’, Komarova, A.I., Strokina, V.M., Soldatenkov, A.T., and Khrustalev, V.N., Zh. Org. Khim., 2008, vol. 44, p. 457; Le Tuan, An’, Levov, A.N., Soldatenkov, A.T., Gruzdev, R.D., and Chyong, Khong, Khieu., Zh. Org. Khim., 2008, vol. 44, p. 463; Levov, A.N., Le Tuan, An’, Soldatenkov, A.T., Chyong, Khong, Khieu, and Khrustalev, V.N., Zh. Org. Khim., 2008, vol. 44, p. 617.Google Scholar
  2. 2.
    Sadym, A.V., Lagunin, A.A., Filimonov, D.A., and Poroikov, V.V., Khim. Farm. Zh., 2002, vol. 36, p. 21.Google Scholar
  3. 3.
    Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Organic Chemistry of Medicines), Moscow: Mir, 2003.Google Scholar
  4. 4.
    Lyapunov, A.Yu., Kirichenko, T.I., Kulygina, E.Yu., and Luk’yanenko, N.G., Zh. Org. Khim., 2005, vol. 41, p. 144.Google Scholar
  5. 5.
    Vatsadze, S.Z., Krainova, Yu.V., Kovalkina, M.A., and Zyk, N.V., Khim. Geterotsikl. Soedin., 2000, p. 1370.Google Scholar
  6. 6.
    Tietze, L.-F. and Eicher, T., Reactions and Syntheses in the Organic Chemistry Laboratory, California: University Science Books, 1989.Google Scholar
  7. 7.
    Sheldrick, G.M., SHELXTL V, 6.12, Structure Determination. Software Suit, Wisconsin, 2001.Google Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • A. N. Levov
    • 1
  • A. I. Komarov
    • 2
  • A. T. Soldatenkov
    • 1
  • G. V. Avramenko
    • 2
  • S. A. Soldatova
    • 1
  • V. N. Khrustalev
    • 3
  1. 1.Russian University of Peoples’ FriendshipMoscowRussia
  2. 2.Mendeleev Russian University of Chemical ProcessingMoscowRussia
  3. 3.Nesmeyanov Institute of Organoelemental CompoundsRussian Academy of SciencesMoscowRussia

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