Russian Journal of Organic Chemistry

, Volume 51, Issue 3, pp 301–308 | Cite as

Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines

  • A. S. Abel
  • A. D. Averin
  • M. V. Anokhin
  • O. A. Maloshitskaya
  • G. M. Butov
  • E. N. Savelyev
  • B. S. Orlinson
  • I. A. Novakov
  • I. P. Beletskaya
Article

Abstract

Copper(I)-catalyzed N-heteroarylation of a wide series of adamantane-containing amines with 2-bromo- and 2- and 3-iodopyridines was studied. The corresponding N-pyridyl derivatives were formed in all cases, but iodopyridines were considerably more reactive. The best results were obtained with the catalytic system CuI-2-(2-methyl-1-oxopropyl)cyclohexanone-DMF which ensured up to 90% yield of the target products. The yield of N-pyridyl derivatives also depended on the steric environment of the amino group in the initial adamantane-containing amine. The yield of the heteroarylation products can be considerably increased using excess iodopyridine. The reaction of 2-(adamantan-1-yl)ethanamine with 2,6-dibromopyridine successfully afforded the corresponding diamine, and N,N′-dipyridyl derivatives were obtained in high yields from 2,2′-(adamantane-1,3-diyl)diethanamine.

Keywords

Catalytic System Cyclohexanone BINOL Triphenylphosphine Oxide Cesium Carbonate 

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Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  • A. S. Abel
    • 1
  • A. D. Averin
    • 1
  • M. V. Anokhin
    • 1
  • O. A. Maloshitskaya
    • 1
  • G. M. Butov
    • 2
  • E. N. Savelyev
    • 3
  • B. S. Orlinson
    • 3
  • I. A. Novakov
    • 3
  • I. P. Beletskaya
    • 1
  1. 1.Faculty of ChemistryMoscow State UniversityMoscowRussia
  2. 2.Volzhsky Polytechnical InstituteVolgograd State Technical UniversityVolzhskii, Volgograd oblastRussia
  3. 3.Volgograd State Technical UniversityVolgogradRussia

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