Russian Chemical Bulletin

, Volume 46, Issue 11, pp 1838–1843

Molecular structure and conformation flexibility of 2-oxo- and 2-thioxo-1,2,3,4-tetrahydropyrimidines and their derivatives

  • O. V. Shishkin
  • E. V. Solomovich
  • V. M. Vakula
  • F. G. Yaremenko
Physical Chemistry


The conformational flexibility and effects of the substituents in 2-oxo- and 2-thioxo-1,2,3,4-tetrahydropyrimidines were studied by the semiempirical quantum-chemical AM1 method. The substituents at the double bond have no appreciable effect on the conformational characteristics of the heterocycle. The introduction of substituents to the saturated carbon atom results in the conversion of the tetrahydrocycle to a half-chair conformation and in a substantial decrease in the ring flexibility. The results of calculations are confirmed by the X-ray study of both compounds.

Key words

2-oxo-1,2,3,4-tetrahydropyrimidine 2-thioxo-1,2,3,4-tetrahydropyrimidine conformational analysis AM1 molecular structure X-ray study 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    O. V. Shishkin, A. S. Polyakova, S. M. Desenko, and Yu. T. Struchkov,Mendeleev Commun., 1994, 182.Google Scholar
  2. 2.
    O. V. Shishkin,J. Mol. Struct., 1996,385, 209.CrossRefGoogle Scholar
  3. 3.
    O. V. Shishkin,Izv. Akad. Nauk, Ser. Khim., 1996, 1934 [Russ. Chem. Bull., 1996,45, 1833 (Engl. Transl.)].Google Scholar
  4. 4.
    O. V. Shishkin,J. Chem. Soc., Chem. Commun., 1995, 1539.Google Scholar
  5. 5.
    M. J. S. Dewar, F. G. Zoebisch, E. F. Healy, and J. J. P. Stewart,J. Am. Chem. Soc. 1985,107, 3902.CrossRefGoogle Scholar
  6. 6.
    V. E. Strel'tsov and V. E. Zavodnik,Kristallografiya, 1989,34, 1369 [Sov. Phys.-Crystallogr., 1989 (Engl. Transl.)].Google Scholar
  7. 7.
    G. M. Sheldrik,SHELXTL PLUS. PC Version 5.02. Program package for crystal structure solution and refinement, Siemens Analytical X-ray Instruments Inc., Germany, 1994.Google Scholar
  8. 8.
    G. M. Sheldrik,SHELXTL PLUS. PC Version 4.2 Program Package for Crystul Structure Solution and Refinement, Siemens Analytical X-ray Instruments Inc., Germany, 1992.Google Scholar
  9. 9.
    N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya,J. Phys. Org. Chem., 1990,3, 143.CrossRefGoogle Scholar
  10. 10.
    O. V. Shishkin, A. S. Polyakova, S. M. Desenko, V. D. Orlov, S. V. Lindeman, and Yu. T. Struchkov,Izv. Akad. Nauk, Ser. Khim., 1994, 1394 [Russ. Chem. Bull., 1994,43, 1320 (Engl. Transl.)].Google Scholar
  11. 11.
    O. V. Shishkin and Yu. T. Struchkov,Izv. Akad. Nauk, Ser. Khim., 1995, 849 [Russ. Chem. Bull., 1995,44, 823 (Engl. Transl.)].Google Scholar
  12. 12.
    Conformational Analysis of Cyclohexenes, Cyclohexadienes and Related Hydrocarbons, Ed. P. W. Rabideau, VCH, New York, 1989, 256 p.Google Scholar
  13. 13.
    T. W. Hambley, L. Phillips, A. C. Poiner, and R. I. Christopherson,Acta Crystallogr., 1993,B49, 130.CrossRefGoogle Scholar
  14. 14.
    C. O. Kappe, G. Urag, P. Roschger, W. Lindner, C. Kratky, and W. Keller,Tetrahedron, 1992,48, 5473.CrossRefGoogle Scholar
  15. 15.
    K. S. Atwall, G. C. Rovnyak, S. D. Kimball, D. M. Floyd, S. Moreland, B. N. Swanson, J. Z. Gougoutas, J. Schwartz, K. M. Smillie, and M. F. Malley,J. Med. Chem., 1990,33, 2629.CrossRefGoogle Scholar
  16. 16.
    Yu. V. Zefirov and P. M. Zorkii,Usp. Khim., 1989,58, 713 [Russ. Chem. Rev., 1989,58 (Engl. Transl.)].Google Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • O. V. Shishkin
    • 1
  • E. V. Solomovich
    • 1
  • V. M. Vakula
    • 2
  • F. G. Yaremenko
    • 2
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation
  2. 2.Ukrainian Institute of Pharmacotherapy of Endocrynologic DeseasesKharkovUkraine

Personalised recommendations