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Synthesis 2007(14): 2215-2221  
DOI: 10.1055/s-2007-983760
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a New Family of Adamantylpyridin-2-amines by Palladium-Catalyzed­ Amination

Alexei D. Averin*a, Elena R. Ranyuka, Svetlana L. Golubb, Alexei K. Buryakb, Evgenii N. Savelyevc, Boris S. Orlinsonc, Ivan A. Novakovc, Irina P. Beletskaya*a
a Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, Moscow 119992, Russian Federation
Fax: +7(495)9393618; e-Mail: averin@org.chem.msu.ru;
b A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, 31 Leninskii prosp., Moscow 119991, Russian Federation
c Volgograd State Technical University, 28 Lenina prosp., Volgograd 400131, Russian Federation
Further Information

Publication History

Received 8 December 2006
Publication Date:
03 July 2007 (online)

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Abstract

Palladium-catalyzed arylation of various adamantane-containing amines with 2-bromopyridine has been studied, and the influence of the phosphane ligand, concentration, and molar ratio of the reagents on the composition of the reaction mixture and on the yield of the target adamantylpyridin-2-amines has been analyzed. The dependence of the formation of N,N-diarylated products on the nature of the starting adamantylamines is shown.

Key words

amines - aminations - homogeneous catalysis - polycycles - pyridines

    References

  • 1 Danielczyk W. J. Neural Transm. Suppl.  1995,  46:  399 
  • 2 Lyons KE. Pahwa R. In Parkinson’s Disease   Ebady M. Pfeiffer R. E. CRC Press; Boca Raton, USA: 2005.  p.685 ; Chem. Abstr. 2005, 143, 89925
  • 3 Smith JP. inventors; WO  9843625 A1.  1998; Chem. Abstr. 1998, 129, 254978
  • 4 Leophonte P. Bull. Acad. Natl. Med.  2005,  189:  341 
  • 5 Hughes PM, Olejnik O, and Schiffman R. inventors; Patent Application US  2005031652.  2005; Chem. Abstr. 2005, 142, 191307
  • 6 Baxter A. Bent J. Bowers K. Braddock M. Brough S. Fagura M. Lawson M. Mclnally T. Mortimore M. Robertson M. Weaver R. Webborn P. Bioorg. Med. Chem. Lett.  2003,  13:  4047 
  • 7 Levina MN. Bull. Exp. Biol. Med.  2005,  139:  337 
  • 8 Wagaw S. Buchwald SL. J. Org. Chem.  1996,  61:  7240 
  • 9 The Pd2(dba)3/dppp system was found to be efficient for the reaction of 1-aminoadamantane with 2-bromopyridine, giving 3a in 60% yield, see: Morton C. O’Shaughnessy P. Scott P. Chem. Commun.  2000,  2099 
  • 10 Wolfe JP. Buchwald SL. J. Org. Chem.  2000,  65:  1144 
  • 11 Beletskaya IP. Bessmertnykh AG. Averin AD. Denat F. Guilard R. Eur. J. Org. Chem.  2005,  261 
  • 12 Wolfe JP. Tomori H. Sadighi JP. Yin J. Buchwald SL. J. Org. Chem.  2000,  65:  1158 
  • 13 Veits YA. Mutsenek EV. Neganova EG. Beletskaya IP. Zh. Org. Khim.  2001,  37:  1657 
  • 14 Ukai T. Kawazura H. Ishii Y. Bonnet JJ. Ibers JA. J. Organomet. Chem.  1974,  65:  253 
  • 15 Jirgensons A. Kauss V. Kalvinsh I. Gold MR. Synthesis  2000,  1709 
  • 16 Gerzon K. Krumkalns EV. Brindle RL. Marshall FJ. Root MA. J. Med. Chem.  1963,  6:  760 
  • 17 Novikov SS, Khardin AP, Radchenko SS, Novakov IA, Orlinson BS, Blinov VF, Gorelov VI, and Zamakh VP. inventors; USSR Patent  682507.  1979; Chem. Abstr. 1979, 91, P193887e