Skip to main content
SpringerLink
Log in

Arylation of adamantanamines: VIII. Optimization of the catalytic system for copper-catalyzed arylation of adamantane-containing amines

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

Abstract

Arylation of adamantane-containing amines with iodobenzene in the presence of copper(I) and copper(II) compounds and various N,N-, N,O- and O,O-bidentate ligands was studied. The best results were obtained using the catalytic system CuI–rac-BINOL [1,1′-bi(naphthalen-2-ol)] (10/20 mol %). Reactions with iodobenzene derivatives containing electron-donor and electron-withdrawing substituents in the para position to the iodine atom were carried out under the optimal conditions.

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. Abel, A.S., Averin, A.D., Anokhin, M.V., Maloshitskaya, O.A., Butov, G.M., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2015, vol. 51, p.301.

    Article  CAS  Google Scholar 

  2. Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, p. 3516.

    Article  CAS  Google Scholar 

  3. May, G. and Peteri, D., Arzneim. Forsch., 1973, vol. 23, p.718.

    CAS  Google Scholar 

  4. Gerzon, K., Krumalns, E.V., Brindle, R.L., Marshall, F.J., and Root, M.A., J. Med. Chem., 1963, vol. 6, p.760.

    Article  CAS  Google Scholar 

  5. Miller, C., Nature, 2008, vol. 451, p.532.

    Article  CAS  Google Scholar 

  6. Sokolov, V.B., Aksinenko, A.Yu., Goreva, T.V., Epishina, T.A., Grigor’ev, V.V., Gabrel’yan, A.V., Vinogradova, D.V., Neganova, M.E., Shevtsova, E.F., and Bachurin, S.O., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, p. 1354.

    Article  CAS  Google Scholar 

  7. Kaur, G., Narayanan, V.L., Risbood, P.A., Hollingshead, M.G., Stinson, S.F., Varma, R.K., and Sausville, E.A., Bioorg. Med. Chem., 2005, vol. 13, p. 1749.

    Article  CAS  Google Scholar 

  8. Brown, A.D., Bunnage, M.E., Glossop, P.A., James, K., Jones, R., Lane, C.A., Lewthwaite, R.A., Mantell, S., Perros-Huguet, C., Price, D.A. Trevethick, M., and Webster, R., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 1280.

    Article  CAS  Google Scholar 

  9. Dover, L.G. and Coxon, G.D., J. Med. Chem., 2011, vol. 54, p. 6157.

    Article  CAS  Google Scholar 

  10. Li, K., Wang, Y., Yang, G., Byun, S., Rao, G., Shoen, C., Yang, H., Gulati, A., Crick, D.C., Cynamon, M., Huang, G., Docampo, R., No, J.H., and Oldfield, E., ACS Infect. Dis., 2015, vol. 1, p.215.

    Article  CAS  Google Scholar 

  11. El-Emam, A.A., Al-Tamimi, A.-M.S., Al-Omar, M.A., Alrashood, K.A., and Habib, E.E., Eur. J. Med. Chem., 2013, vol. 68, p.96.

    Article  CAS  Google Scholar 

  12. El-Emam, A.A., Al-Deeb, O.A., Al-Omar, M.A., and Lehmann, J., Bioorg. Med. Chem., 2004, vol. 12, p. 5107.

    Article  CAS  Google Scholar 

  13. Kim, S.H., Bok, J.H., Lee, J.H., Kim, I.H., Kwon, S.W., Lee, G.B., Kang, S.K., Park, J.S., Jung, W.H., Kim, H.Y., Rhee, S.D., Ahn, S.H., Bae, M.A., Ha, D.C., Kim, K.Y., and Ahn, J.H., ACS Med. Chem. Lett., 2012, vol. 3, p.88.

    Article  Google Scholar 

  14. Ryu, J.H., Lee, J.A., Kim, S., Shin, Ya., Yang, J., Han, H.Y., Son, H.J., Kim, Y.H., Sa, J.H., Kim, J.-S., Lee, J., Lee, J., and Park, H.-G., J. Med. Chem., 2016, vol. 59, p. 10176.

    Article  CAS  Google Scholar 

  15. Silhar, P., Eubanks, L.M., Seki, H., Pellett, S., Javor, S., Tepp, W.H., Johnson, E.A., and Janda, K.D., J. Med. Chem., 2013, vol. 56, p. 7870.

    Article  CAS  Google Scholar 

  16. Panchenko, S.P., Abel, A.S., Averin, A.D., Maloshitskaya, O.A., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, p. 1550.

    Article  CAS  Google Scholar 

  17. Averin, A.D., Ranyuk, E.R., Golub, S.L., Buryak, A.K., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Synthesis, 2007, p. 2215.

    Google Scholar 

  18. Averin, A.D., Ulanovskaya, M.A., Kovalev, V.V., Buryak, A.K., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2010, vol. 46, p.64.

    Article  CAS  Google Scholar 

  19. Averin, A.D., Ulanovskaya, M.A., Buryak, A.K., Savel’ev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2010, vol. 46, p. 1790.

    Article  CAS  Google Scholar 

  20. Averin, A.D., Ulanovskaya, M.A., Buryak, A.K., Savel’ev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2011, vol. 47, p.30.

    Article  CAS  Google Scholar 

  21. Grigorova, O.K., Averin, A.D., Abel, A.S., Maloshitskaya, O.A., Kovalev, V.V., Savelev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2012, vol. 48, p. 1391.

    Article  CAS  Google Scholar 

  22. Grigorova, O.K., Averin, A.D., Abel, A.S., Maloshitskaya, O.A., Butov, G.M., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2012, vol. 48, p. 1495.

    Article  CAS  Google Scholar 

  23. Averin, A.D., Baranova, T.Yu., Abel, A.S., Kovalev, V.V., Buryak, A.K., Butov, G.M., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2013, vol. 49, p.1.

    Article  CAS  Google Scholar 

  24. Abel, A.S., Averin, A.D., Maloshitskaya, O.A., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Molecules, 2013, vol. 18, p. 2096.

    Article  CAS  Google Scholar 

  25. Gopalan, B., Thomas, A., and Shah, D.M., WO Patent Appl. no. 2006 090 244, 2006; Chem. Abstr., 2006, vol. 145, no. 292604.

    Google Scholar 

  26. Novakov, I.A., Kulev, I.A., Radchenko, S.S., Birznieks, K.A., Boreko, E.I., Vladyko, G.V., and Korobchenko, L.V., Pharm. Chem. J., 1987, vol. 21, p.287.

    Article  Google Scholar 

  27. Popov, Yu.V., Mokhov, V.M., and Tankabekyan, N.A., Russ. J. Appl. Chem., 2013, vol. 86, p.404.

    Article  CAS  Google Scholar 

  28. Novikov, S.S., Khardin, A.P., Radchenko, S.S., Novakov, I.A., Orlinson, B.S., Blinov, V.F., Gorelov, V.I., and Zamakh, V.P., USSR Inventor’s Certificate no. 682 507, 1979; Chem. Abstr., 1979, vol. 91, no. P193887e.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Leninskie gory 1–3, Moscow, 119991, Russia

    S. P. Panchenko, A. S. Abel, A. D. Averin, O. A. Maloshitskaya & I. P. Beletskaya

  2. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr. 31-4, Moscow, 119071, Russia

    A. D. Averin & I. P. Beletskaya

  3. Volgograd State Technical University, pr. Lenina 28, Volgograd, 400005, Russia

    E. N. Savelyev, B. S. Orlinson & I. A. Novakov

Authors
  1. S. P. Panchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Abel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. D. Averin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. A. Maloshitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. N. Savelyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. B. S. Orlinson
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. I. A. Novakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. 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 © S.P. Panchenko, A.S. Abel’, A.D. Averin, O.A. Maloshitskaya, E.N. Savelyev, B.S. Orlinson, I.A. Novakov, I.P. Beletskaya, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 10, pp. 1471–1478.

For communication VII, see [1].

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Panchenko, S.P., Abel, A.S., Averin, A.D. et al. Arylation of adamantanamines: VIII. Optimization of the catalytic system for copper-catalyzed arylation of adamantane-containing amines. Russ J Org Chem 53, 1497–1504 (2017). https://doi.org/10.1134/S1070428017100025

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017100025

Search

Navigation