Skip to main content
Log in

Synthesis and properties of sym-triazine derivatives. 6. Synthesis of 2-amino- and 2,4-diamino-sym-triazines containing sterically hindered phenol segments

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Amino-4,6-disubstituted-sym-triazines containing sterically hindered phenol segments were synthesized by cyclocondensation of N-acrylguanidines with nitriles or thiocyanates. The same compounds can be obtained by condensation of N-acylguanidine with iminoester hydrochlorides. The reaction of methyl Β-(4-hydroxy-3,5-di-tert-butylphenyl)propionate with biguanides gives N-substituted 2,4-diamino-6-R-sym-triazines that contain a shielded phenol residue.

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. V. I. Kelarev, M. Bellul', R. A. Karakhanov, Dibi Ammar, and A. F. Lunin, Khim. Geterotsikl. Soedin., No. 3, 356 (1987).

    Google Scholar 

  2. O. V. Malova, V. I. Kelarev, I. A. Golubeva, T. P. Vishnyakova, and A. F. Lunin, Zh. Vses. Khim. O., 29, No. 4, 462 (1984).

    Google Scholar 

  3. O. V. Malova, T. P. Vishnyakova, I. A. Golubeva, V. I. Kelarev, and A. F. Lunin, Khim. Geterotsikl. Soedin., No. 12, 1678 (1984).

    Google Scholar 

  4. P. B. Russell, G. H. Hitchings, B. H. Chase, and J. Walker, J. Am. Chem. Soc., 74, 5403 (1952).

    Google Scholar 

  5. H. Kabbe, K. Eiter, and E. Möller, Annalen, 704, 140 (1963).

    Google Scholar 

  6. V. I. Kelarev, S. G. Shvekhgeimer, V. N. Koshelev, A. F. Lunin, and G. A. Shvekhgeimer, Zh. Vses. Khim. O., No. 5, 582 (1982).

    Google Scholar 

  7. S. L. Shapiro, V. A. Parrino, K. Geiger, S. Kobrin, and L. Freedman, J. Am. Chem. Soc., 79, 5064 (1957).

    Google Scholar 

  8. E. M. Smolin and L. Rapoport, S-Triazine and Derivatives, Interscience, New York, London (1959), p. 224.

    Google Scholar 

  9. A. Kreutzberger, Adv. Chem. Soc., 34, 208 (1962).

    Google Scholar 

  10. V. V. Ershov, G. A. Nikiforov, and A. A. Volod'kin, Sterically Hindered Phenols [in Russian], Khimiya, Moscow (1972).

    Google Scholar 

  11. M. Avram and G. Hatteescu [sic], Infrared Spectroscopy, Wiley Interscience (1970), p. 527.

  12. A. I. Finkel'shtein and E. N. Boitsov, Usp. Khim., 31, 1496 (1982).

    Google Scholar 

  13. A. R. Katritzky (ed.), Physical Methods in the Chemistry of Heterocyclic Compounds, Academic Press, New York (1963).

    Google Scholar 

  14. V. I. Kelarev, Dibi Ammar, A. F. Lunin, R. L. Ushakova, A. I. Mikaya, N. V. Petrova, and S. G. Shvekhgeimer, Zh. Org. Khim., 19, 2401 (1983).

    Google Scholar 

  15. A. I. Finkel'shtein, Opt. Spektrosk., 5, 264 (1958).

    Google Scholar 

  16. A. R. Katritzky and R. A. Jones, J. Chem. Soc., 3674 (1959).

  17. T. N. Pliev, Zh. Prikl. Spektrosk., 13, 124 (1970).

    Google Scholar 

  18. W. Traube, Berichte, 43, 3580 (1910).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

For Communication 5, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1392–1397, October, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kelarev, V.I., Yakh'ya, F.L., Karakhanov, R.A. et al. Synthesis and properties of sym-triazine derivatives. 6. Synthesis of 2-amino- and 2,4-diamino-sym-triazines containing sterically hindered phenol segments. Chem Heterocycl Compd 23, 1118–1123 (1987). https://doi.org/10.1007/BF00476544

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00476544

Keywords

Navigation