Chemistry of Heterocyclic Compounds

, Volume 14, Issue 9, pp 1019–1024 | Cite as


LXIV. Structure and properties of 1,3-diaryldihydrobenzo[f]quinazolines
  • M. A. Mikhaleva
  • G. N. Chernikova
  • V. P. Mamaev


It is shown that the 1,3-diaryldihydrobenzo[f]quinazolines that are formed in the condensation of β-naphthylamine, an aromatic aldehyde, and ammonia are 1,2-dihydro isomers. They readily form salts due to the developing stabilization of the molecule by resonance of the amidinium type. Thus 2,4-dialkylbenzo [f] quinazolinium iodides rather than monoalkyl derivatives were obtained in the case of alkylation with alkyl halides as a result of refluxing the reaction mixtures. The isomeric monoalkylbenzoquinazolinium iodides, the structure of which was proved by the formation of the known benzoquinazolines after treatment with alkali, were also obtained.


Ammonia Organic Chemistry Aldehyde Iodide Pyrimidine 
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Literature cited

  1. 1.
    V. P. Borovik, L. Yu. Ivanovskaya, and V. P. Mamaev, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim., Nauk, No. 14, 110 (1977).Google Scholar
  2. 2.
    M. A. Mikhaleva, G. N. Chernikova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 1, 100 (1978).Google Scholar
  3. 3.
    A. Weissberger (editor), The Chemistry of Heterocyclic Compounds, Vol. 24, Part I, Wiley-Interscience (1967).Google Scholar
  4. 4.
    R. F. Smith, P. C. Briggs, R. A. Kent, J. A. Albricht, and E. J. Walsh, J. Heterocycl. Chem., 2, 157 (1965).Google Scholar
  5. 5.
    J. G. Smith, J. M. Sheepy, and E. M. Levy, J. Org. Chem., 41, 497 (1976).Google Scholar
  6. 6.
    J. G. Smith, and J. M. Sheepy, J. Heterocycl. Chem., 12, 231 (1975).Google Scholar
  7. 7.
    M. Lora-Tamayo, R. Madronero, and G. G. Munoz, Chem. Ber., 94, 208 (1961).Google Scholar
  8. 8.
    G. Kempter, H.-J. Ziegner, and G. Moser, Z. Chem., 11, 12 (1971).Google Scholar
  9. 9.
    R. B. Williams, J. Am. Chem. Soc., 64, 1395 (1942).Google Scholar
  10. 10.
    W. L. F. Armarego, J. Chem. Soc., No. 7, 2697 (1961).Google Scholar
  11. 11.
    K. Yamauchi, M. Hayashi, and M. Kinoshita, J. Org. Chem., 40, 385 (1975).Google Scholar
  12. 12.
    O. A. Zagulyaeva, and V. P. Mamaev, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 12, 137 (1968).Google Scholar
  13. 13.
    R. V. Coombs, R. P. Danna, M. Denzer, G. E. Hardtmann, B. Huegi, G. Koletar, and H. Ott, J. Med. Chem., 16, 1237 (1973).Google Scholar
  14. 14.
    N. V. Sidgwick, The Organic Chemistry of Nitrogen, Clarendon Press, Oxford (1966), pp. 421, 438.Google Scholar
  15. 15.
    Y. Yamada, T. Oine, and I. Inoue, Bull. Chem. Soc. Jpn., 47, 343 (1974).Google Scholar
  16. 16.
    D. Lloyd and H. J. McNab, J. Chem. Soc., Perkin Trans. I, No. 16, 1784 (1976).Google Scholar
  17. 17.
    N. J. Leonard and L. E. Brady, J. Org. Chem., 30, 817 (1965).Google Scholar
  18. 18.
    T. L. Pilicheva, O. N. Chupakhin, and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., No. 4, 561 (1975).Google Scholar
  19. 19.
    W. Girke, Tetrahedron Lett., No. 39, 3537 (1976).Google Scholar
  20. 20.
    D. Lloyd and H. McNab, Angew. Chem., 88, 496 (1976).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • M. A. Mikhaleva
    • 1
  • G. N. Chernikova
    • 1
  • V. P. Mamaev
    • 1
  1. 1.Novosibirsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRNovosibirsk

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