Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 879–886 | Cite as

Synthesis, crystal and molecular structure of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide

  • O. V. Kulikov
  • A. V. Mazepa


The acylation of the syn isomer of the oxime of 2-amino-5-methylbenzophenone with 4-chlorobutyryl chloride gives a mixture of the anti isomer of the 4-chlorobutyryloximine of 2-(4-chlorobutyryl)amino-5-methylbenzophenone and 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide. The crystal and molecular structure of this oxide was established by X-ray diffraction structural analysis. The molecule is planar. The electron impact fragmentation of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide was discussed.


quinazoline mass spectrometry X-ray diffraction structural analysis 


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  1. 1.
    O. V. Kulikov, S. A. Andronati, V. I. Pavlovskii, O. V. Mazepa, and T. A. Kabanova, Visnyk ONU, 5, No. 2, 68 (2000).Google Scholar
  2. 2.
    V. I. Pavlovsky and O. V. Kulikov, in: V. G. Kartsev (editor), Selected Methods for Synthesis and Modification of Heterocycles, Vol. 1, IBS Press, Moscow (2002), p. 542.Google Scholar
  3. 3.
    S. A. Andronati, Yu. A. Simonov, V. I. Pavlovsky, O. V. Kulikov, M. Gdanets, and A. V. Mazepa, Zh. Obshch. Khim., 75, 969 (2005).Google Scholar
  4. 4.
    L. H. Sternbach, E. Reeder, O. Keller, and W. Metlesics, J. Org. Chem., 26, 4488 (1961).CrossRefGoogle Scholar
  5. 5.
    V. I. Pavlovsky, O. V. Kulikov, T. L. Karaseva, T. A. Kabanova, A. V. Mazepa, and S. I. Andronati, Ukr. Khim. Zh., 64, 123 (1998).Google Scholar
  6. 6.
    G. I. Gordiichuk, S. A. Andronati, T. A. Voronina, N. Kh. Rakhmankulova, P. B. Terentiev, P. A. Sharbatyan, and A. S. Yarovskii, in: Physiologically Active Compounds [in Russian], Vol. 14, Naukova Dumka, Kiev (1982), p. 36.Google Scholar
  7. 7.
    E. V. Gromachevskaya, E. A. Kaigorodova, S. I. Firgang, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1222 (2005). [Chem. Heterocycl. Comp., 41, 1045 (2005)].Google Scholar
  8. 8.
    O. V. Kulikov, V. I. Pavlovsky, A. V. Mazepa, and S. A. Andronati, Khim. Geterotsikl. Soedin., 566 (2003). [Chem. Heterocycl. Comp., 39, 485 (2003)].Google Scholar
  9. 9.
    S. Bogentoft and B. Danielsson, J. Heterocycl. Chem., 9, 193 (1972).Google Scholar
  10. 10.
    M. Ferrugia, M. L. Bajardi, L. Ceraulo, and S. Plescia, J. Heteocycl. Chem., 29, 565 (1992).CrossRefGoogle Scholar
  11. 11.
    O. V. Kulikov, I. G. Filippova, M. Gdanets, V. I. Pavlovsky, and Yu. A. Simonov, Zh. Struktur. Khim., 47, 346 (2006).Google Scholar
  12. 12.
    D. Hunter, D. G. Neilson, and T. J. R. Weakley, J. Chem. Soc., Perkin Trans. 1, 2709 (1985).Google Scholar
  13. 13.
    S. V. Lindeman, V. E. Shklover, Yu. T. Struchkov, I. I. Ponomarev, and S. A. Saling, Izv. Akad. Nauk SSSR, Ser. Khim., 1637 (1986).Google Scholar
  14. 14.
    G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, Ver. 5.1 (1998).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • O. V. Kulikov
    • 1
  • A. V. Mazepa
    • 1
  1. 1.A. B. Bogatsky Physico-Chemical InstituteNational Academy of Sciences of UkraineOdessaUkraine

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