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Heteroadamantanes and their derivatives. 6. Synthesis and mass-spectrometric investigation of 5-mono- and 5,6-disubtituted 6-oxo-1,3-diazaadamantanes

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Abstract

The corresponding 5-mono- and 5,7-disubstituted 6-oxo-1,3-diazaadamantanes were obtained with high yields by the condensation of mono- and α,α'-disubstituted acetones with hexamethylenetetramine in the presence of glacial acetic acid, and their structures were confirmed by IR and PMR spectra. The behavior of the compounds under electron impact was studied, and the main fragmentation paths of their molecules were determined.

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Literature cited

  1. 1.

    A. I. Kuznetsov, E. B. Basargin, M. Kh. Ba, P. F. Yakushev, and B. V. Unkovskii, Zh. Org. Khim.,21, No. 12 (1985).

  2. 2.

    T. Sasaki, Adv. Heterocycl. Chem.,30, 80 (1982).

  3. 3.

    Z. Kafka and V. Galik, Sb. Vys. Svcol. Chem. Technol. Praze,D44, 349 (1981).

  4. 4.

    H. Stetter, J. Schafer, and K. Dieminger, Chem. Ber.,91, 598 (1958).

  5. 5.

    S. Chiavarelli and G. Settimj, Gazz. Chim. Ital.,88, 1234 (1958).

  6. 6.

    H. Stetter, K. Dieminger, and E. Rauscher, Chem. Ber.,92, 2057 (1959).

  7. 7.

    A. I. Kuznetsov, P. F. Yakushev, and B. V. Unkovskii, Zh. Org. Khim.,10, 841 (1974).

  8. 8.

    A. I. Kuznetsov, I. P. Boiko, T. D. Sokolova, E. B. Basargin, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 5, 661 (1985).

  9. 9.

    J. Kuthan and J. Palecek, Collect. Czech. Chem. Commun.,28, 2260 (1963).

  10. 10.

    P. F. Yakushev, A. I. Kuznetsov, V. V. Tolstikov, and B. V. Unkovskii, Zh. Org. Khim.,13, 2452 (1977).

  11. 11.

    Ts. E. Agadzhanyan and G. L. Arutyunyan, Arm. Khim. Zh.,34, 963 (1981).

  12. 12.

    Z. Dolejsek, S. Hala, V. Hanus, and S. Landa, Collect. Czech. Chem. Commun.,31, 435 (1966).

  13. 13.

    A. A. Polyakova, E. V. Khramova, E. I. Bagrii, N. N. Tsitsugina, I. M. Lukashenko, T. Yu. Frid, and P. I. Sanin, Neftekhimiya13, 9 (1973).

  14. 14.

    K. K. Khullar, C. L. Bell, and L. Bauer, J. Org. Chem.,38, 1042 (1973).

  15. 15.

    P. A. Sharbatyan, P. B. Terent'ev, V. V. Kovalev, and E. A. Shokova, Zh. Org. Khim.,16, 308 (1980).

  16. 16.

    O. S. Chizhov, S. S. Novikov, N. F. Karpenko, A. G. Yurchenko, and G. I. Danilenko, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1028 (1972).

  17. 17.

    N. F. Karpenko, O. S. Chizhov, S. S. Novikov, A. G. Yurchenko, and G. I. Danilenko, Izv. Akad. Nauk SSSR, Ser. Khim. No. 2, 337 (1972).

  18. 18.

    G. Eckhardt, and H. U. Fehlhaber, Org. Hass Spectrum.,7, 485 (1973).

  19. 19.

    A. S. Moskovkin, A. I. Kuznetsov, and I. V. Miroshnichenko, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol.,24, 172 (1981).

  20. 20.

    J. Kuthan, J. Palecek, and L. Musil, Collect. Czech. Chem. Commun.,38, 3491 (1973).

  21. 21.

    T. Sasaki, S. Equchi, T. Kiriyama, and Y. Sakito, J. Org. Chem., 38, 1648 (1973).

  22. 22.

    I. Mitera, P. Zakharzh, I. Burchard, and L. Vodichka, Sb. Vys. Scol. Chem. Technol. Praze,D32, 79 (1976).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1679–1685, December, 1985.

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Kuznetsov, A.I., Basargin, E.B., Moskovkin, A.S. et al. Heteroadamantanes and their derivatives. 6. Synthesis and mass-spectrometric investigation of 5-mono- and 5,6-disubtituted 6-oxo-1,3-diazaadamantanes. Chem Heterocycl Compd 21, 1382–1388 (1985). https://doi.org/10.1007/BF00842964

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Keywords

  • Acetic
  • Acetone
  • Acetic Acid
  • Organic Chemistry
  • Glacial Acetic Acid