Skip to main content
SpringerLink
Log in

Arylation of adamantanamines: IV. Palladium-catalyzed arylation of amines of adamantane series with isomeric chloroquinolines

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

Abstract

Palladium-catalyzed arylation of diverse amines of the adamantane series with isomeric chloroquinolines was investigated. The 2-chloroquinoline is the most reactive, however the best yields of the N-arylation products are most frequently obtained in the reaction with the less reactive 6-chloroquinoline. The applicability of the reaction is limited by the size of the substituent at the amino group. In some instances the noncatalytic amination of chloroquinolines was possible.

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. Averin, A.D., Ulanovskaya, M.A., Buryak, A.K., Savel’ev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Zh. Org. Khim., 2011, vol. 47, p. 35.

    Google Scholar 

  2. Bagrii, E.I., Adamantany: poluchenie, svoistva, primenenie (Adamantanes: Synthesis, Properites, Application), Moscow: Nauka, 1989.

    Google Scholar 

  3. Kamyanov, I.M., Polis, Ya.Yu. and Kupisk, A.G., Midantan i ego primenenie v terapii i profilaktike neirolepticheskogo sindroma (Amantadine and Its Application in Treatment and Prevention of Neuroleptic Syndrome), Riga: Zinatne, 1973.

    Google Scholar 

  4. Gilligan, B.S., Veale, J., and Wodak, J., Med. J. Austral., 1970, vol. 2, p. 634.

    CAS  Google Scholar 

  5. Dolin, R. and Bentley, D.W., Options Contr. Influenza. Proc. Viratek-Ucla, Symp., Keystone. Apr., 20–25, 1985, New York: 1986.

  6. Svenson, T.N., Eur. J. Pharm., 1973, vol. 34, p. 232.

    Google Scholar 

  7. Klimova, N.V., Zaitseva, N.M., Avdyunina, N.I., Pyatin, B.M., Morozov, I.S., Bykov, N.P., and Kuz’min, V.I., Khim.-Farm. Zh., 1990, p. 26.

  8. Morozov, I.S., Petrov, V.I., and Sergeeva, S.A., Farmakologiya adamantanov (Pharmacology of Adamantanes), Volgograd: Izd. Volgograd. Med. Akad., 2001.

    Google Scholar 

  9. Avdyunina, N.I., Morozov, I.S., Bol’shakova, R.F., Militareva, N.A., Klimova, N.A., Pyatin, B.M., Khranilov, A.A., and Dvalishvili, E.G., Khim.-Farm. Zh., 1988, 819.

  10. Da Settimo, A., Marini, A.M., Primofiore, G., and da Settimo, F., Farmacology, 1995, vol. 50, p. 321.

    Google Scholar 

  11. Ficarra, R., Ficarra, P., Tommasini, A., Fenech, G., Pizzementi, F.C., and Bisignano, G., Bull. Chim. Farm., 1984, vol. 123, p. 317.

    CAS  Google Scholar 

  12. Ismail, F.M.D., Dascombe, M.I., Carrand, P., and North, S.E., J. Pharm. Pharmacol., 1996, vol. 48, p. 841.

    Article  CAS  Google Scholar 

  13. Gerzon, K., US Patent 3730956, 1971; Chem. Abstr., 1973, vol. 79, P18597r.

  14. Aranyi, P., Bata, I., Batory, S., Boronkay, E., Bovy, P., Kapui, Z., Edit, S., Szabo, T., Urban-Szabo, K., and Varga, M., WO Patent WO2005021536, 2003; Chem. Abstr., 2005, vol. 142, 298122.

  15. Abdulqader, A., Alhaider, M., Abdelkader, A., and Lien, E.J., J. Med. Chem., 1985, vol. 28, p. 1394.

    Article  Google Scholar 

  16. Asagarasu, A., Matsui, T., Hayashi, H., Tamaoki, S., Yamauchi, Y., Minato, K., and Sato, M., J. Med. Chem., 2010, vol. 53, p. 7549.

    Article  CAS  Google Scholar 

  17. Nasr, M., Drach, J., Smith, S., Shipman, C. Jr., and Burckhaltert, J.H., J. Med. Chem., 1988, vol. 31, p. 1347.

    Article  CAS  Google Scholar 

  18. Beauchard, A., Jaunet, A., Murillo, L., Baldeyrou, B., Lansiaux, A., Cherrouvrier, J., Domona, L., Picot, L., Bailly, C., Besson, T., and Thierry, V., Eur. J. Med. Chem., 2009, vol. 44, p. 3858.

    Article  CAS  Google Scholar 

  19. Sayed, I., van der Veken, P., Steert, K., Dhooghe, L., Hostyn, S., V. Baelen, G., Lemiere, G., Bert, U., Maes, W., Cos, P., Maes, L., Joossens, J., Haemers, A., Pieters, L., and Augustyns, K., J. Med. Chem., 2009, vol. 52, p. 2979.

    Article  Google Scholar 

  20. Deraeve, C., Maraval, A., Vendier, L., Faugeroux, V., Pitié, M., and Meunier, B., Eur. J. Inorg. Chem., 2008, p. 5622.

  21. Lundgren, R.J., Sappong-Kumankumah, A., and Stradiotto, M., Chem. Eur. J., 2010, vol. 16, p. 1983.

    Article  CAS  Google Scholar 

  22. Michalik, D., Kumar, K., Zapf, A., Tillack, A., Arlt, M., Heinrich, T., and Beller, M., Tetrahedron Lett., 2004, vol. 45, p. 2057.

    Article  CAS  Google Scholar 

  23. Knight, R., Allen, D., Birch, H., Chapman, G., Galvin, F., Jopling, L., Lock, C., Meissner, W. G.J., Owen, D., Raphy, G., Watson, R.J., and Williams, S., Bioorg. Med. Chem. Lett., 2008, p. 629.

  24. Rataboul, F., Zapf, A., Jackstell, R., Harkal, S., Riermeier, T., Monsees, A., Dingerdissen, U., and Beller, M., Chem. Eur. J., 2004, vol. 10, p. 2983.

    Article  CAS  Google Scholar 

  25. Toma, G., Fujita, K., and Yamaguchi, R., Eur. J. Org. Chem., 2009, p. 4586.

  26. Manolikakes, G., Gavryushin, A., and Knochel, P., J. Org. Chem., 2008, vol. 73, p. 1429.

    Article  CAS  Google Scholar 

  27. Musonda, C.C., Whitlock, G.A., Witty, M. J., Brun, R., and Kaiser, M., Bioorg. Med. Chem. Lett., 2009, p. 481.

  28. Sanchez-Martın, R., Campos, M.J., Conejo-Garcia, A., Cruz-Lopez, O., Banez-Coronel, M., Rodrıguez-Gonzalez, A., Gallo, A.M., Lacal, C.J., and Espinosa, A., J. Med. Chem., 2005, vol. 48, p. 3354.

    Article  Google Scholar 

  29. Pinard, E., Alanine, A., Bourson, A., Buttelmann, B., Heitz, M.-P., Mutel, V., Gill, R., Trube, T., and Pharma, R., Bioorg. Med. Chem. Lett., 2002, p. 2615.

  30. Ghosh, B., Antonio, T., Reith, E.A.M., and Dutta, K.A., J. Med. Chem., 2010, vol. 53, p. 2114.

    Article  CAS  Google Scholar 

  31. Girault, S., Grellier, P., Berecibar, A., Maes, L., Lemiere, P., Mouray, E., Davioud-Charvet, E., and Sergheraert, C., J. Med. Chem., 2001, vol. 44, p. 1658.

    Article  CAS  Google Scholar 

  32. Abeywickrama, S., Rotenberg, A.S., and Baker, A.D., Bioorg. Med. Chem. Lett., 2006, p. 7796.

  33. Wolf, C. and Lerebours, R., J. Org. Chem., 2003, vol. 68, p. 7077.

    Article  CAS  Google Scholar 

  34. Scott, D.A., Bell, J.K., Campbell, T.C., Cook, J.D., Dakin, A.L., Valle, J.D., Drew, L., Gero, W.T., Hattersley, M.M., Omer, C.A., Tyurin, B., and Zheng, X., Bioorg. Med. Chem. Lett., 2009, p. 701.

  35. Zhu, C., Hansen, R.A., Bateman, T., Chen, Z., Holt, G.T., Hubert, A.J., Karanam, V.B., Lee, J.S., Pan, J., Su, Qian, Reddy, B.G.V., Reitman, L.M., Strack, M.A., Tong, V., Weingarth, T.D., Wolff, M.S., McNeil, J.D., Weber, E.A., Duffy, L.J., and Edmondson, D.S., Bioorg. Med. Chem. Lett., 2008, p. 4393.

  36. Beletskaya, I.P., Tsvetkov, A.V., Tsvetkov, P.V., Latyshev, G.V., and Lukashev, N.V., Izv. Akad. Nauk, Ser. Khim., 2005, vol. 54, p. 210.

    Google Scholar 

  37. Smith, A.J., Jones, K.R., Booker, W.G., and Pyke, M.S., J. Org. Chem., 2008, vol. 73, p. 8880.

    Article  CAS  Google Scholar 

  38. Anderson, W.K., Tundel, E.R., Ikawa, T., Altman, A.R., and Buchwald, S.L., Angew. Chem., Int. Ed., 2006, vol. 45, p. 6523.

    Article  CAS  Google Scholar 

  39. Averin, A.D., Ulanovskaya, M.A., Kovalev, V.V., Buryak, A.K., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Zh. Org. Khim., 2010, vol. 46, p. 64.

    CAS  Google Scholar 

  40. Averin, A.D., Ulanovskaya, M.A., Buryak, A.K., Savel’ev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Zh. Org. Khim., 2010, 46, p. 1779.

    Google Scholar 

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

  42. Ranyuk, E.R., Averin, A.D., Buryak, A.K., Savel’ev, E.N., Orlin-son, B.S., Novakov, I.A., and Beletskaya, I.P., Zh. Org. Khim., 2009, vol. 45, p. 1569.

    Google Scholar 

  43. Averin, A.D., Ranyuk, E.R., Buryak, A.K., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Mendeleev Commun., 2009, vol. 19, p. 136.

    Article  CAS  Google Scholar 

  44. Gopalan, B., Thomas, A., and Shah, D.M., PCT Int. Appl. WO 2006090244, 2006; Chem. Abstr., 2006, vol. 145, 292604.

  45. 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. 454.

    Article  CAS  Google Scholar 

  46. Jirgensons, A., Kauss, V., Kalvinsh, I., and Gold, M., Synthesis, 2000, 1709.

  47. Lavrova, L.N., Klimova, N.V., Shmar’yan, M.I., Ul’yanova, O.V., Vikhlyaev, Yu.I., and Skoldinov, A.P., Zh. Org. Khim., 1974, vol. 10, p. 761.

    CAS  Google Scholar 

  48. 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. Lomonosov Moscow State University, Moscow, 119991, Russia

    O. K. Grigorova, A. D. Averin, A. S. Abel, O. A. Maloshitskaya, V. V. Kovalev & I. P. Beletskaya

  2. Volgograd State Technical University, Volgograd, Russia

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

Authors
  1. O. K. Grigorova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. D. Averin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. S. Abel
    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. V. V. Kovalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. N. Savelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. B. S. Orlinson
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. I. A. Novakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. 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 English Text © O.K. Grigorova, A.D. Averin, A.S. Abel, O.A. Maloshitskaya, V.V. Kovalev, E.N. Savelev, B.S. Orlinson, I.A. Novakov, I.P. Beletskaya, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 11, pp. 1397–1411.

For Communication III, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Grigorova, O.K., Averin, A.D., Abel, A.S. et al. Arylation of adamantanamines: IV. Palladium-catalyzed arylation of amines of adamantane series with isomeric chloroquinolines. Russ J Org Chem 48, 1391–1406 (2012). https://doi.org/10.1134/S1070428012110012

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428012110012

Keywords

Search

Navigation