Chemistry of Heterocyclic Compounds

, Volume 48, Issue 10, pp 1492–1502 | Cite as

Studies on quinazoline chemistry. 5.* Synthesis of 3,4-dihydroquinazolines with functional substituents at C-2 atom and their alkylation reactions

  • E. V. Gromachevskaya
  • E. A. Kaigorodova
  • K. S. Pushkareva
  • G. D. Krapivin

Syntheses are reported for a new series of 2-substituted 4,4-diphenyl-3,4-dihydroquinazolines by the reaction of o-aminophenyldiphenylcarbinol (APC) with various nitriles. The reaction of APC with substituted 5-bromo-3-cyano-2(1H)-pyridones leads to the formation of derivatives of two products: 3,4-dihydroquinazolines and 4H-3,1-benzoxazines. The alkylation of 3,4-dihydroquinazolines using dimethyl sulfate proceeds through N,N-dimethylation. The structure of these products is a function of the nature of the substituent at C-2 atom of the heterocycle.


dimethyl sulfate 4,4-diphenyl-3,4-dihydroquinazolines alkylation mass-spectral fragmentation 


  1. 1.
    E. V. Gromachevskaya, E. A. Kaigorodova, V. E. Zavodnik, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 886 (2007). [Chem. Heterocycl. Compd., 43, 748 (2007)].Google Scholar
  2. 2.
    E. V. Gromachevskaya, G. D. Krapivin, F. V. Kvitkovskii, A. O. Shein, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., 640 (2001). [Chem. Heterocycl. Compd., 37, 588 (2001)].Google Scholar
  3. 3.
    E. V. Gromachevskaya, E. A. Kaigorodova, S. I. Firgang, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1222 (2005). [Chem. Heterocycl. Compd., 41, 1045 (2005)].Google Scholar
  4. 4.
    V. I. Ivanskii, Chemistry of Heterocyclic Compounds [in Russian], Vyssh. Shkola, Moscow (1978), pp. 16–28.Google Scholar
  5. 5.
    V. G. Kul'nevich, E. V. Gromachevskaya, and T. P. Kosulina, Khim. Geterotsikl. Soedin., 953 (1984). [Chem. Heterocycl. Compd., 20, 776 (1984)].Google Scholar
  6. 6.
    E. V. Gromachevskaya, T. P. Kosulina, A. L. Chekhun, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., 542 (1993). [Chem. Heterocycl. Compd., 29, 465 (1993)].Google Scholar
  7. 7.
    E. V. Gromachevskaya, T. P. Kosulina, V. G. Kul'nevich, Yu. Yu. Samitov, A. I. Khayarov, and V. T. Dubonosov, Khim. Geterotsikl. Soedin., 101 (1990). [Chem. Heterocycl. Compd., 26, 86 (1990)].Google Scholar
  8. 8.
    A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Moscow (1972), p. 327.Google Scholar
  9. 9.
    E. V. Gromachevskaya, T. P. Kosulina, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., 537 (1993). [Chem. Heterocycl. Compd., 29, 460 (1993)].Google Scholar
  10. 10.
    E. V. Gromachevskaya, V. G. Kul'nevich, T. P. Kosulina, and V. S. Pustovarov, Khim. Geterotsikl. Soedin., 842 (1988). [Chem. Heterocycl. Compd., 24, 692 (1988)].Google Scholar
  11. 11.
    K. Weygand, Experimental Methods in Organic Chemistry [Russian translation], Khimiya, Moscow (1968), p. 944.Google Scholar
  12. 12.
    A. D. Cross, Introduction to Practical Infrared Spectroscopy [Russian translation], Izd. Inostr. Lit., Moscow (1961), p. 97.Google Scholar
  13. 13.
    J. Mathieu and R. Panico, Course of Theoretical Principles of Organic Chemistry [Russian translation], Mir, Moscow (1975), p. 381.Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • E. V. Gromachevskaya
    • 1
  • E. A. Kaigorodova
    • 2
  • K. S. Pushkareva
    • 3
  • G. D. Krapivin
    • 1
  1. 1.Kuban State Technological UniversityKrasnodarRussia
  2. 2.Kuban State Agrarian UniversityKrasnodarRussia
  3. 3.Kuban State UniversityKrasnodarRussia

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