Russian Chemical Bulletin

, Volume 55, Issue 7, pp 1229–1238 | Cite as

Synthesis of new 3,4-di-and 1,2,3,4-tetrahydroquinazolin-4-one derivatives and X-ray diffraction study of crystal solvates of 3-methylsulfonylamino-2-(2-methylsulfonylaminophenyl)-1,2,3,4-tetrahydroquinazolin-4-one

  • L. Yu. Ukhin
  • L. G. Kuz’mina


The reactions of hydrazide, mesyl hydrazide, succinyl hydrazide, and maleyl hydrazide of anthranilic acid with carbonyl compounds were studied, and new di-and tetrahydroquinazolin-4-one derivatives were prepared. The structure of one reaction product, viz., 3-methylsulfonylamino-2-(2-methylsulfonylaminophenyl)-1,2,3,4-tetrahydroquinazolin-4-one, was established by X-ray diffraction study of two crystal solvates of this compound. The characteristic features of the crystal packings of these solvates are discussed.

Key words

anthranilic acid hydrazide anthranilic acid mesyl hydrazide succinic anhydride maleic anhydride carbonyl compounds di-and tetrahydroquinazolin-4-one derivatives supramolecular architecture 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    S. Gabriel and J. Colman, Ber., 1904, 37, 3643.Google Scholar
  2. 2.
    C. Parkanyi, H. L. Yuan, B. H. E. Strömberg, and A. Evenzahav, J. Heterocycl. Chem., 1992, 29, 749.Google Scholar
  3. 3.
    P. K. Mohanta and K. Kim, Heterocycles, 2002, 57, 1471.CrossRefGoogle Scholar
  4. 4.
    H. Böhme and H. Böing, Arch. Pharm., 1960, 293, 1011.CrossRefGoogle Scholar
  5. 5.
    R. H. Klemm, J. Wang, and L. Hawkins, J. Heterocycl. Chem., 1995, 32, 1039.Google Scholar
  6. 6.
    R. H. Klemm, T. J. R. Weakley, R. D. Gilbertson, and Yang-Heon-Song, J. Heterocycl. Chem., 1998, 35, 1269.CrossRefGoogle Scholar
  7. 7.
    J. Lessel, Arch. Pharm. (Weinheim), 1994, 327, 571.CrossRefGoogle Scholar
  8. 8.
    L. A. Shemchuk, Zh. Org. Khim., 1998, 34, 568 [Russ. J. Org. Chem., 1998, 34 (Engl. Transl.)].Google Scholar
  9. 9.
    L. Yu. Ukhin and L. G. Kuz’mina, Izv. Akad. Nauk, Ser. Khim., 2004, 2165 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2262].Google Scholar
  10. 10.
    D. Meth-Cohn, B. Narine, and B. Tarnowski, Tetrahedron Lett., 1997, 33, 3111.Google Scholar
  11. 11.
    L. Yu. Ukhin, K. Yu. Suponitskii, and V. G. Kartsev, Khim. Prirod. Soedin., 2003, 395 [Chem. Nat. Compd., 2003 (Engl. Transl.)].Google Scholar
  12. 12.
    SAINT. Version 6.02A, Bruker AXS Inc., Madison (Wisconsin, USA), 2001.Google Scholar
  13. 13.
    SHELXTL-Plus, Release 5.10, Bruker AXS Inc., Madison (Wisconsin, USA), 1997.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • L. Yu. Ukhin
    • 1
  • L. G. Kuz’mina
    • 2
  1. 1.Institute of Physical and Organic ChemistryRostov State UniversityRostov-on-DonRussian Federation
  2. 2.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations