Skip to main content
Log in

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

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. M. D. Taylor, K. R. Anderson, and E. W. Badger, J. Heterocycl. Chem., 26, 1353 (1989).

    Google Scholar 

  2. R. J. Chorvat and K. J. Rorig, J. Org. Chem., 53, 5779 (1988).

    Google Scholar 

  3. K. S. Atwal, G. C. Rovnjak, B. C. O'Reilly, and J. Schwartz, J. Org. Chem., 54, 5898 (1989).

    Google Scholar 

  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. 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. 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. 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. P. O. Vitolinya and A. A. Kimenis, Khim.-farm. Zh., No. 3, 285 (1989).

    Google Scholar 

  9. P. Biginelli, Ber., 24, 1317 (1891).

    Google Scholar 

  10. K. Folkers, H. J. Harwood, and T. B. Jonson, J. Am. Chem. Soc., 54, 3751 (1932).

    Google Scholar 

  11. B. C. O'Reilly and K. S. Atwal, Heterocycles, 26, 1185 (1987).

    Google Scholar 

  12. Ch. O. Kappe and P. Roschger, J. Heterocycl. Chem., 26, 55 (1989).

    Google Scholar 

  13. N. Tsuda, T. Mishina, M. Obata, K. Araki, and T. Nakamura, Jpn. Pat. Appl. 62-77387; Ref. Zh. Khim., 14 O 132P (1988).

  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).

  15. Z. D. Dubovenko and V. P. Mamaev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., No. 3, 101 (1972).

    Google Scholar 

  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. Ch. D. Nurd and M. E. Nilson, J. Org. Chem., 20, 927 (1955).

    Google Scholar 

  18. A. Dornow and W. Sassenberg, Ann., 602, 14 (1957).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 3, pp. 388–392, March, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Remennikov, G.Y., Boldyrev, I.V., Kapran, N.A. et al. Synthesis and some conversions of 6-methyl- and 1,6-dimethyl-5-nitro-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidines. Chem Heterocycl Compd 29, 325–329 (1993). https://doi.org/10.1007/BF00531510

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00531510

Keywords

Navigation