Advertisement

Russian Journal of Organic Chemistry

, Volume 49, Issue 1, pp 1–7 | Cite as

Arylation of adamantanamines: VI. Palladium-catalyzed arylation of amines and diamines of the adamantane series with 3-bromopyridine

  • A. D. Averin
  • T. Yu. Baranova
  • A. S. Abel
  • V. V. Kovalev
  • A. K. Buryak
  • G. M. Butov
  • E. N. Savelyev
  • B. S. Orlinson
  • I. A. Novakov
  • I. P. Beletskaya
Article

Abstract

Palladium-catalyzed amination of 3-bromopyridine with amines of the adamantane series in the presence of Pd(dba)2/L [L = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl or 2-dimethylamino-2′-dicyclohexylphosphinobiphenyl] gave the desired N-(pyridin-3-yl)-substituted amines in 74–97% yields. Diamines of the adamantane series reacted with 2 equiv of 3-bromopyridine in a complicated fashion to produce mono- and triaryl-substituted derivatives as by-products, while the yields of N,N′-diarylation products were 18–56%.

Keywords

BINAP Binaphthyl Anhydrous Dioxane Adamantane Series Light Yellow Oily Substance 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    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.CrossRefGoogle Scholar
  2. 2.
    Morozov, I.S., Petrov, V.I., and Sergeeva, S.A., Farmakologiya adamantanov (Pharmacology of Adamantanes), Volgograd: Volgograd. Med. Akad., 2001.Google Scholar
  3. 3.
    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, no. 1, p. 26.Google Scholar
  4. 4.
    Avdyunina, N.I., Klimova, N.V., Kuz’min, V.I., Morozov, I.S., Pyatin, B.M., and Smirnov, L.D., Russian Patent no. 1 055 105, 1992; Chem. Abstr., 1992, vol. 117, no. P 124 497w.Google Scholar
  5. 5.
    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.CrossRefGoogle Scholar
  6. 6.
    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.CrossRefGoogle Scholar
  7. 7.
    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.CrossRefGoogle Scholar
  8. 8.
    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
  9. 9.
    Gopalan, B., Thomas, A., and Shah, D.M., PCT Int. Appl. WO 2006 090 244, 2006; Chem. Abstr., 2006, vol. 145, no. 292 604.Google Scholar
  10. 10.
    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, 1978; Chem. Abstr., 1979, vol. 91, no. P 193 887 e.Google Scholar
  11. 11.
    Jirgensons, A., Kauss, V., Kalvinsh, I., and Gold, M., Synthesis, 2000, p. 1709.Google Scholar
  12. 12.
    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.Google Scholar
  13. 13.
    Ukai, T., Kawazura, H., Ishii, Y., Bonnet, J.J., and Ibers, J.A., J. Organomet. Chem., 1974, vol. 65, p. 253.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • A. D. Averin
    • 1
    • 2
  • T. Yu. Baranova
    • 1
  • A. S. Abel
    • 1
  • V. V. Kovalev
    • 1
  • A. K. Buryak
    • 2
  • G. M. Butov
    • 3
  • E. N. Savelyev
    • 4
  • B. S. Orlinson
    • 4
  • I. A. Novakov
    • 4
  • I. P. Beletskaya
    • 1
    • 2
  1. 1.Faculty of ChemistryMoscow State UniversityMoscowRussia
  2. 2.Frumkin Institute of Physical Chemistry and ElectrochemistryRussian Academy of SciencesMoscowRussia
  3. 3.Volzhsky Polytechnical InstituteVolzhskiiRussia
  4. 4.Volgograd State Technical UniversityVolgogradRussia

Personalised recommendations