Skip to main content
SpringerLink
Log in

Synthesis and properties of derivatives ofsym-triazine. 15. Synthesis of amine derivatives ofsym-triazine that contain indole groups

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

By the cyclocondensation of imino esters of acids of the indole series with N-acylguanidines, 2-amino-4,6-disubstituted sym-triazine are obtained that contain indole groups. The reaction of N-(indolyl-3-imidolyl)-guanidine with esters of carboxylic acids leads to 2-amino-4-(3-indolyl)-6-substituted sym-triazines. Indolyl-containing N-subsitituted 2,4-diamino-sym-trizines are synthesized by the reaction of imino esters of indole acids with biguanides. Similar products are also formed when 2-amino-4-trichloromethyl-sym-triazines that contain indole substituents react with dimethylamine, morpholine, or furfurylamine.

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

Access this article

Log in via an institution

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. V. I. Kelarev, V. N. Koshelev, and R. A. Karakhanov, Khim. Geterotsikl. Soedin., No. 1, 111 (1995).

  2. V. I. Kelarev, R. A. Karakhanov, M. Bellul, R. L. Ushakova, and A. I. Mikaya, Khim. Geterotsikl. Soedin., No. 5, 674 (1988).

  3. V. I. Kelarev, R. A. Karakhanov, A. S. Kokosova, and G. D. Gankin, Khim. Geterotsikl. Soedin., No. 9, 1250 (1992).

  4. R. A. Karakhanov, V. I. Kelarev, A. S. Kokosova, V. A. Malyshev, and V. I. Zav'yalov, Zh. Org. Khim.,28, No. 8, 1750 (1992).

    Google Scholar 

  5. V. I. Kelarev, V. N. Koshelev, N. V. Belov, O. V. Malova, and R. A. Karakhanov, Khim. Geterotsikl. Soedin., No. 8, 1125 (1994).

  6. E. M. Bondarenko, S. E. Semenov, I. N. Makarenko, and N. N. Suvorov, Tr. MKhTI im D. I. Mendeleev, Issue 149, 61 (1987).

  7. V. I. Kelarev, R. A. Karakhanov, A. S. Kokosova, I. V. Kochetkova, and I. I. Patalakh, Abstr. IXth Sym. Chem. Heterocyclic Cmpds., Bratislava (1987), p. 195.

  8. J. Kosary, E. Kasztreiner, G. Rabloszky, and M. Kurthy, Eur. J. Med. Chem.,24, 97 (1989).

    Google Scholar 

  9. V. I. Kelarev, R. A. Karakhanov, Yu. N. Polivin, A. M. Kuatbekov, A. S. Remizov, and A. I. Mikaya, Khim. Geterotsikl. Soedin., No. 9, 1271 (1993).

  10. H. Nagasaka, E. Joshikawa, and K. Odo, J. Synth. Org. Chem. Jpn.,25, 1048 (1967).

    Google Scholar 

  11. S. L. Shapiro, V. A. Parrino, K. Geiger, S. Kobrin, and L. Freedman, J. Am. Chem. Soc.,79, No. 18, 5064 (1957).

    Google Scholar 

  12. E. M. Smolin and L. S. Rapoport, s-Triazine and Derivatives, Interscience, New York (1959), p. 1219.

    Google Scholar 

  13. V. I. Kelarev, Dibi Ammar, and A. F. Lunin, Khim. Geterotsikl. Soedin.,No. 11, 1557 (1985).

  14. V. I. Kelarev, F. Yakh'ya Laauad, R. A. Karakhanov, I. A. Golubeva, T. P. Nishnyakova, and O. V. Malova, Khim. Geterotsikl. Soedin., No. 5, 681 (1988).

  15. A. I. Finkel'shtein and E. N. Boitsov, Usp. Khim.,31, 1496 (1962).

    Google Scholar 

  16. A. R. Katritzky (.), Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow-Leningrad (1966), p. 515, 594.

    Google Scholar 

  17. W. Houlihan (.), Indoles, Vol. 1, Interscience, New York (1972), p. 15.

    Google Scholar 

  18. A. I. Finkel'shtein, Opt. Spektroskop.,5, 264 (1958).

    Google Scholar 

  19. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York (1970), p. 21.

    Google Scholar 

  20. É. Ya. Lukevits (ed.), Progress in Furan Chemistry [in Russian], Zinatne, Riga (1978), p. 19.

    Google Scholar 

  21. P. N. Preston, P. W. Steedman, M. H. Palmer, S. M. Mackenzie, and M. F. Stevens, Org. Mass Spectrom., No. 7, 863 (1970.

  22. Q. H. Porter and J. Baldes, Mass Spectrometry of Heterocyclic Compounds, Wiley-Interscience, New York (1971). p. 376.

    Google Scholar 

  23. R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1974).

  24. D. L. von Minden, J. D. Liehr, and M. H. Wilson, J. Org. Chem.,39, 285 (1975).

    Google Scholar 

  25. V. I. Kelarev and G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., No. 5, 645 (1980).

  26. V. I. Kelarev, R. A. Karakhanov, S. Sh. Gasanov, Yu. N. Polivin, and A. I. Mikaya, Zh. Org. Khim,29, 763 (1993).

    Google Scholar 

  27. W. Traube, Ber.,43, 3590 (1910).

    Google Scholar 

  28. A. A. Zmolyarchuk, A. P. Kobernik, N. I. Ivanova, N. M Skvortsov, and Yu. V. Aleksashin, Khim.-farm. Zh.,10, 72 (1976).

    Google Scholar 

  29. V. I. Kelarev, M. Bellul, V. I. Zav'yalov, Dibi Ammar, A. N. Golovin, E. A. Lisitsyn, and R. A. Karakhanov, Zh. Org. Khim.,24, 1100 (1988).

    Google Scholar 

  30. S. L. Shapiro, V. A. Parrino, and L. Freedman, JAMC,81, 3728 (1959).

    Google Scholar 

Download references

Authors
  1. V. I. Kelarev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. N. Koshelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. V. Morozova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. A. Karakhanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. S. Remizov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

I. M. Gubkin State Petroleum and Gas Academy, Moscow, 117917. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–223, February, 1995. Original article submitted December 21, 1994.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kelarev, V.I., Koshelev, V.N., Morozova, G.V. et al. Synthesis and properties of derivatives ofsym-triazine. 15. Synthesis of amine derivatives ofsym-triazine that contain indole groups. Chem Heterocycl Compd 31, 186–194 (1995). https://doi.org/10.1007/BF01169678

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01169678

Keywords

Search

Navigation