Skip to main content
SpringerLink
Log in

Synthesis of nitrogen- and oxygen-containing macrocycles with several polyamine and anthracene or anthraquinone fragments in reactions of palladium-catalyzed amination

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Palladium-catalyzed amination of 1,8-dichloroanthracene and 1,8-dichloroanthraquinone with polyamines made it possible to synthesize bis(haloaryl)-substituted polyamines and oxadiamines, 1,8-bis-(polyamino)substituted anthracenes and anthraquinones. The dependence of the yield of synthesized main and side products on the reaction conditions and on the nature of initial compounds was investigated. The cyclization of compounds obtained was performed leading to cyclodimers and cyclotrimers, and the limitations of this method were established. A possibility was examined of preparation of N,N-diarylated polyamines derivatives in reactions with excess 1,8-dichloroanthracene or 1,8-dichloroanthraquinone.

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. Beletskaya, I.P., Averin, A.D., Borisenko, A.A., Denat, F., and Guilard, R., Tetrahedron Lett., 2003, vol. 44, 1433.

    Article  Google Scholar 

  2. Beletskaya, I.P., Averin, A.D., Pleshkova, N.A., Borisenko, A.A., Serebryakova, M.V., Denat, F., and Guilard, R., Synlett., 2005, no. 1, p. 87.

  3. Beletskaya, I.P., Averin, A.D., Ulanovskaya, O.A., Fedotenko, I.A., Borisenko, A.A., Serebryakova, M.V., Denat, F., and Guilard, R., Chem. Lett., 2005, vol. 34, p. 1100.

    Article  CAS  Google Scholar 

  4. Averin, A.D., Ulanovskaya, O.A., Fedotenko, I.A., Borisenko, A.A., Serebryakova, M.V., and Beletskaya, I.P., Helv. Chim. Acta, 2005, vol. 88, p. 1983.

    Article  CAS  Google Scholar 

  5. Beletskaya, I.P., Bessmertnykh, A.G., Averin, A.D., Denat, F., and Guilard, R., Eur. J. Org. Chem., 2005, no. 2, p. 281.

  6. Witulski, B., Weber, M., Bergstraesser, U., Desvergne, J.-P., Bassani, D.M., and Bouas-Laurent, H., Org. Lett., 2001, vol. 3, p. 1467.

    Article  CAS  Google Scholar 

  7. Meyer, S., Andrioletti, B., Sessler, J.L., and Lynch, V., J. Org. Chem., 1998, vol. 63, p. 6752.

    Article  CAS  Google Scholar 

  8. Kaufmann, H.L., Liable-Sands, L., Rheingold, A.L., and Burgmayer, S.J.N., Inorg. Chem., 1999, vol. 38, p. 2592.

    Article  CAS  Google Scholar 

  9. Ruiz-Molina, D., Veciana, J., Wurst, K., Hendrickson, D.N., and Rovira, C., Inorg. Chem., 2000, vol. 39, p. 617.

    Article  CAS  Google Scholar 

  10. Collman, J.P., Hutchinson, J.E., Lopez, M.A., Tabard, A., Guilard, R., Seok, W.K., Ibers, J.A., and L’Her, M., J. Am. Chem. Soc., 1992, vol. 114, p. 9869.

    Article  CAS  Google Scholar 

  11. Collman, J.P., Wagenknecht, P.S., and Hutchinson, J.E., Angew Chem. Int. Ed., 1994, vol. 33, p. 1537.

    Article  Google Scholar 

  12. Lachkar, M., Tabard, A., Brandes, S., Guilard, R., Atmani, A., De, Cian, A., Fischer, J., and Weiss, R., Inorg. Chem., 1997, vol. 36, p. 4141.

    Article  CAS  Google Scholar 

  13. Bridger, G.J., Skerlj, R.T., Thornton, D., Padmanabhan, S., Martelluc, S.A., Henson, G.W., Abrams, M.J., Yamamoto, N., De, Vreese, K., Pauwels, R., De and Clercq, E., J. Med. Chem., 1995, vol. 38, p. 366.

    Article  CAS  Google Scholar 

  14. Jerome, F., Gros, C.P., Tardieux, C., Barbe, J.-M., and Guilard, R., Chem. Commun., 1998, p. 2007.

  15. Bissell, R.A., Calle, E., DeSilva, A.P., DeSilva, S.A., Gunaratne, H.Q.N., Habib-Jiwan, J.-L., Peiris, S.L.A., Rupasinghe, R.A.D.D., Samarasinghe, T.K.S.D., Sandanayake, K.R.A.S., and Soumillon, J.-P., J. Chem. Soc., Perkin, Trans. 2, 1992, p. 1559.

  16. Marquis, D., Desvergne, J.-P., and Bouas-Laurent, H., J. Org. Chem., 1995, vol. 60, p. 7984.

    Article  CAS  Google Scholar 

  17. Tucker, J.H.R., Bouas-Laurent, H., Marsau, P., Riley, S.W., and Desvergne, J.-P., Chem. Commun., 1997, p. 1165.

  18. DeSantis, G., Fabbrizzi, L., Licchelli, M., Mangano, C., Sacchi, D., and Sardone, N., Inorg. Chim. Acta, 1997, vol. 257, p. 69.

    Article  CAS  Google Scholar 

  19. Belfield, A.J., Brown, G.R., and Foubister, A.J., Tetrahedron, 1999, vol. 55, p. 11399.

    Article  CAS  Google Scholar 

  20. Haenel, M.W., Oevers, S., Bruckmann, J., Kuhnig, J., and Kruger, C., Synlett., 1998, p. 301.

  21. Yang, B.H. and Buchwald, S.L., J. Organometal. Chem., 1999, vol. 576, p. 125; Hartwig, J.F., Angew Chem. Int. Ed., 1998, vol. 37, p. 2046.

    Article  CAS  Google Scholar 

  22. Wolfe, J.P., Tomori, H., Sadighi, J.P., Yin, J., and Buchwald, S.L., J. Org. Chem., 2000, 65, p. 1158.

    Article  CAS  Google Scholar 

  23. Nishiyama, M., Yamamoto, T., and Koie, Y., Tetrahedron Lett., 1998, vol. 39, p. 617.

    Article  CAS  Google Scholar 

  24. Grasa, G.A., Viciu, M.S., Huang, J., and Nolan, S.P., J. Org. Chem., 2001, vol. 66, p. 7729.

    Article  CAS  Google Scholar 

  25. Gradel, B., Brenner, E., Schneider, R., and Fort, Y., Tetrahedron, Lett., 2001, vol. 42, p. 5689.

    Article  CAS  Google Scholar 

  26. Averin, A.D., Shukhaev, A.V., Golub, S.L., Buryak, A.K., and Beletskaya, I.P., Synthesis, 2007, vol. 19, p. 2995.

    Article  Google Scholar 

  27. Averin, A.D., Ranyuk, E.R., Lukashev, N.V., and Beletskaya, I.P., Chem. Eur. J., 2005, vol. 11, p. 1730.

    Article  Google Scholar 

  28. Golden, R. and Stock, L.M., J. Am. Chem. Soc., 1972, vol. 94, p. 3080.

    Article  CAS  Google Scholar 

  29. Ukai, T., Kawazura, H., Ishii, Y., Bonnet, J.J., and Ibers, J.A., J. Organometal. Chem., 1974, vol. 65, p. 253.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Moscow State University, Moscow, 119992, Russia

    A. D. Averin, E. P. Ranyuk & I. P. Beletskaya

  2. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russia

    A. K. Buryak

Authors
  1. A. D. Averin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. P. Ranyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. K. Buryak
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. P. Beletskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. D. Averin.

Additional information

Original Russian Text © A.D. Averin, E.P. Ranyuk, A.K. Buryak, I.P. Beletskaya, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 11, pp. 1694–1708.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Averin, A.D., Ranyuk, E.P., Buryak, A.K. et al. Synthesis of nitrogen- and oxygen-containing macrocycles with several polyamine and anthracene or anthraquinone fragments in reactions of palladium-catalyzed amination. Russ J Org Chem 44, 1671–1685 (2008). https://doi.org/10.1134/S1070428008110195

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008110195

Keywords

Search

Navigation