Skip to main content
Log in

Pyrimidines. 70. Relative reactivities of the chlorine atoms of 2,2′,4-trichloro-4′,5-dipyrimidinyl in its reaction with piperidine

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2,2′,4-Trichloro-6′-phenyl-4′,5-dipyrimidinyl, for which nucleophilic substitution with piperdine under various conditions was studied, was obtained from 2,2′,4-trioxo-6′-phenyl-1, 1′,2,2′,3,4-hexahydro-4′,5-dipyrimidinyl. It is shown that there is an appreciable difference in the rates of substitution of the first, second, and third chlorine atoms, and this made it possible to obtain reaction products that contain one, two, and three piperidino groups. The chlorine atom in the 4 position is replaced initially, after which the chlorine atom in the 2 position undergoes substitution. The structures of the compounds were proved by chemical transformations and analysis of the PMR spectra.

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

Literature cited

  1. M. A. Mikhaleva, V. V. Gulevich, I. I. Naumenko, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 5, 678 (1979).

    Google Scholar 

  2. R. Pater, J. Heterocycl. Chem., 8, 743 (1971).

    Google Scholar 

  3. S. -H. Chang, I. Y. Koo, and Y. H. Kim, J. Korean Chem. Soc., 18, 210 (1974).

    Google Scholar 

  4. D. J. Brown, The Pyrimidines, Supplement I, Wiley (1970), p. 280.

  5. A. R. Surrey and R. A. Culter, J. Am. Chem. Soc., 76, 1109 (1954).

    Google Scholar 

  6. W. Pfleiderer and K. -H. Schündehütte, Ann., 612, 158 (1958).

    Google Scholar 

  7. V. P. Mamaev, O. A. Zagulyaeva, and S. M. Shein, Khim. Geterotsikl. Soedin., No. 6, 723 (1973).

    Google Scholar 

  8. V. P. Mamaev, O. A. Zagulyaeva, and V. P. Krivopalov, Dokl. Akad. Nauk SSSR, 193, 600 (1970).

    Google Scholar 

  9. G. E. Hubert, J. Am. Chem. Soc., 56, 190 (1934).

    Google Scholar 

  10. D. J. Brown and N. W. Jakobsen, J. Chem. Soc., No. 8, 3172 (1962).

    Google Scholar 

  11. The Sadtler Standard Spectra, Sadtler Research Laboratory, Philadelphia, NMR Spectrum No. 5484.

  12. T. Koyama, T. Hirota, C. Basho, Y. Watanabe, Y. Kitauchi, Y. Satoh, S. Ohmori, and M. Yamato, Chem. Pharm. Bull., 24, 1459 (1976).

    Google Scholar 

  13. O. P. Shkurko and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 4, 526 (1978).

    Google Scholar 

  14. O. P. Shkurko and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 5, 673 (1978).

    Google Scholar 

  15. O. P. Shkurko and V. P. Mamaev, Zh. Org. Khim., (1979, in press).

  16. V. P. Mamaev, O. A. Zagulyaeva, S. M. Shein, A. I. Shvets, and V. P. Krivopalov, Reakts. Sposobn. Org. Soedin., 5, 824 (1968).

    Google Scholar 

  17. D. W. Allen, D. J. Buckland, B. G. Hutley, A. C. Oades, and J. B. Turner, J. Chem. Soc., Perkin I, No. 6, 621 (1977).

    Google Scholar 

  18. É. A. Arutyunyan, V. I. Gunar, and S. I. Zav'yalov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 904 (1970).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for communication 69.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 821–826, June, 1979.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mikhaleva, M.A., Naumenko, I.I. & Mamaev, V.P. Pyrimidines. 70. Relative reactivities of the chlorine atoms of 2,2′,4-trichloro-4′,5-dipyrimidinyl in its reaction with piperidine. Chem Heterocycl Compd 15, 671–676 (1979). https://doi.org/10.1007/BF00539506

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00539506

Keywords

Navigation