Skip to main content
Log in

Synthesis and some conversions of 4-aryl-6-methyl-2-methoxy(phenyl)-5-nitro-1,4-dihydropyrimidines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 1-arylidene-1-nitropropan-2-ones with O-methylisourea (or benzamidine) in the presence of aluminum oxide gave 4-aryl-6-methyl-2-methoxy(phenyl)-5-nitro-1,4-dihydropyrimidines. It was shown that the reactions of the compounds synthesized with electrophilic agents proceed at the exocyclic methyl group, as well as at the N(1), N(3), and C(5) atoms of the 1,4-dihydropyrimidine fragment of the molecule.

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.

Similar content being viewed by others

References

  1. A. L. Weis and H. C. van der Plas, Heterocycles, Vol. 24 (1986), p. 1433.

    Google Scholar 

  2. A. L. Weis, Advances in Heterocyclic Chemistry, Academic Press, Orlando (1985), p. 3.

    Google Scholar 

  3. H. Cho, K. Shima, M. Hayashimatsu, Y. Ohnaka, A. Mizuno, and Y. Takeuchi, J. Org. Chem., 50, 4227 (1985).

    Google Scholar 

  4. K. S. Atwal, G. C. Rovnyak, B. C. O'Reilly, and J. Schwarte, J. Org. Chem., 54, 5898 (1989).

    Google Scholar 

  5. 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 

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

    Google Scholar 

  8. H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, Y. Takeuchi, M. Hamaguchi, K. Aisaka, T. Hudaka, M. Kawai, M. Takeda, T. Ischihara, K. Funahashi, F. Satoh, M. Morita, and T. Noguchi, J. Med. Chem., 32, 2399 (1989).

    Google Scholar 

  9. K. S. Atwal, G. C. Rovnyak, J. Schwartz, S. Moreland, A. Hedberg, J. Z. Gougoutas, M. F. Malley, and D. M. Floyd, J. Med. Chem., 33, 1510 (1990).

    Google Scholar 

  10. K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, and B. C. O'Reilli, J. Med. Chem., 34, 806 (1991).

    Google Scholar 

  11. S. I. Zav'yalov and L. B. Kulikova, Khim. farm. Zh., No. 7, 116 (1992).

    Google Scholar 

  12. Ch. O. Kappe and P. Roschger, J. Heterocycl. Chem., 26, No. 1, 55 (1989).

    Google Scholar 

  13. N. Tsuda, T. Misina, M. Okhata, K. Araki, D. Inui, and T. Nakamura, Claim 62-270584 Japan. R. Zh. Kh., 3084P (1989).

  14. N. Tsuda, T. Misina, M. Okhata, K. Araki, and T. Nakamura, Claim 62-77387 Japan. R. Zh. Kh., 140132P (1988).

  15. 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 

  16. G. Ya. Remennikov, I. V. Boldyrev, N. A. Kapran, and L. K. Kurilenko, Khim. Geterotsikl. Soedin., No. 3, 388 (1993).

    Google Scholar 

  17. G. Ya. Remennikov, I. V. Boldyrev, S. A. Kravchenko, and V. V. Pirozhenko, Khim. Geterotsikl. Soedin., No. 9, 12190 (1993).

    Google Scholar 

  18. H. Cho, T. Iwashita, M. Ueda, A. Mizuno, K. Mizukawa, and M. Hamaguchi, J. Am. Chem. Soc., 110, 4832 (1988).

    Google Scholar 

  19. V. M. Cherkasov, G. Ya. Remennikov, and E. A. Romanenko, Khim. Geterotsikl. Soedin., No. 6, 823 (1981).

    Google Scholar 

  20. A. Ya. Il'chenko, G. Ya. Remennikov, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 9, 1260 (1981).

    Google Scholar 

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

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1398–1404, October, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Remennikov, G.Y., Boldyrev, I.V., Kravchenko, S.A. et al. Synthesis and some conversions of 4-aryl-6-methyl-2-methoxy(phenyl)-5-nitro-1,4-dihydropyrimidines. Chem Heterocycl Compd 29, 1200–1205 (1993). https://doi.org/10.1007/BF00538068

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00538068

Keywords

Navigation