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.
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Original Russian Text © 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, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 319–326.
For communication VI, see [1].
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Abel, A.S., Averin, A.D., Anokhin, M.V. et al. Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines. Russ J Org Chem 51, 301–308 (2015). https://doi.org/10.1134/S1070428015030021
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DOI: https://doi.org/10.1134/S1070428015030021