Chemistry of Heterocyclic Compounds

, Volume 29, Issue 3, pp 325–329 | Cite as

Synthesis and some conversions of 6-methyl- and 1,6-dimethyl-5-nitro-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidines

  • G. Ya. Remennikov
  • I. V. Boldyrev
  • N. A. Kapran
  • L. K. Kurilenko


Using a modification of the Biginelli reaction, we have synthesized 6-methyl- and 1,6-dimethyl-5-nitro-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidines. We have studied some of their chemical conversions involving the methyl group on the C(6) atom, the nitrogen atoms of the pyrimidine ring, and the phenyl substituent.


Nitrogen Methyl Organic Chemistry Phenyl Nitrogen Atom 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    M. D. Taylor, K. R. Anderson, and E. W. Badger, J. Heterocycl. Chem., 26, 1353 (1989).Google Scholar
  2. 2.
    R. J. Chorvat and K. J. Rorig, J. Org. Chem., 53, 5779 (1988).Google Scholar
  3. 3.
    K. S. Atwal, G. C. Rovnjak, B. C. O'Reilly, and J. Schwartz, J. Org. Chem., 54, 5898 (1989).Google Scholar
  4. 4.
    H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, Y. Nakeuchi, M. Hamaguchi, K. Aisaka, T. Hidaka, M. Kawai, M. Takeda, T. Ishihara, K. Funahashi, F. Satoh, M. Morita, and T. Noguchi, J. Med. Chem., 32, 2399 (1989).Google Scholar
  5. 5.
    K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, and B. C. O'Reilly, J. Med. Chem., 34, 806 (1991).Google Scholar
  6. 6.
    E. L. Khanina, G. O. Silinietse, Ya. Ya. Ozol, G. Ya. Dubur, and A. A. Kimenis, Khim.-farm. Zh., No. 10, 72 (1978).Google Scholar
  7. 7.
    K. S. Atwal, 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., 33, 2629 (1990).Google Scholar
  8. 8.
    P. O. Vitolinya and A. A. Kimenis, Khim.-farm. Zh., No. 3, 285 (1989).Google Scholar
  9. 9.
    P. Biginelli, Ber., 24, 1317 (1891).Google Scholar
  10. 10.
    K. Folkers, H. J. Harwood, and T. B. Jonson, J. Am. Chem. Soc., 54, 3751 (1932).Google Scholar
  11. 11.
    B. C. O'Reilly and K. S. Atwal, Heterocycles, 26, 1185 (1987).Google Scholar
  12. 12.
    Ch. O. Kappe and P. Roschger, J. Heterocycl. Chem., 26, 55 (1989).Google Scholar
  13. 13.
    N. Tsuda, T. Mishina, M. Obata, K. Araki, and T. Nakamura, Jpn. Pat. Appl. 62-77387; Ref. Zh. Khim., 14 O 132P (1988).Google Scholar
  14. 14.
    N. Tsuda, T. Mishina, M. Obata, K. Araki, A. Inui, and T. Nakamura, Jpn. Pat. Appl. 62-270584; Ref. Zh. Khim., 3 O 84P (1989).Google Scholar
  15. 15.
    Z. D. Dubovenko and V. P. Mamaev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., No. 3, 101 (1972).Google Scholar
  16. 16.
    G. Ya. Remennikov, S. S. Shavaran, I. V. Boldyrev, L. K. Kurilenko, B. M. Klebanov, and V. P. Kukhar', Khim.- farm. Zh., No. 3, 35 (1991).Google Scholar
  17. 17.
    Ch. D. Nurd and M. E. Nilson, J. Org. Chem., 20, 927 (1955).Google Scholar
  18. 18.
    A. Dornow and W. Sassenberg, Ann., 602, 14 (1957).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • G. Ya. Remennikov
    • 1
  • I. V. Boldyrev
    • 1
  • N. A. Kapran
    • 1
  • L. K. Kurilenko
    • 1
  1. 1.Institute of Bioorganic Chemistry and PetrochemistryUkrainian Academy of SciencesKiev

Personalised recommendations