caa a22 4500 605529728 CHVBK 20210128100820.0 cr unu---uuuuu 210128e20150301xx s 000 0 eng 10.1134/S1070428015030021 doi (NATIONALLICENCE)springer-10.1134/S1070428015030021 Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines [Elektronische Daten] [A. Abel, A. Averin, M. Anokhin, O. Maloshitskaya, G. Butov, E. Savelyev, B. Orlinson, I. Novakov, I. Beletskaya] 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. Pleiades Publishing, Ltd., 2015 Abel A. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut Averin A. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut Anokhin M. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut Maloshitskaya O. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut Butov G. Volzhsky Polytechnical Institute, Volgograd State Technical University, ul. Engel'sa 42a, 404130, Volzhskii, Volgograd oblast, Russia aut Savelyev E. Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia aut Orlinson B. Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia aut Novakov I. Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia aut Beletskaya I. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut Russian Journal of Organic Chemistry Pleiades Publishing 51/3(2015-03-01), 301-308 1070-4280 51:3<301 2015 51 11178 https://doi.org/10.1134/S1070428015030021 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015030021 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Abel A. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut NATIONALLICENCE 700 1- Averin A. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut NATIONALLICENCE 700 1- Anokhin M. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut NATIONALLICENCE 700 1- Maloshitskaya O. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut NATIONALLICENCE 700 1- Butov G. Volzhsky Polytechnical Institute, Volgograd State Technical University, ul. Engel'sa 42a, 404130, Volzhskii, Volgograd oblast, Russia aut NATIONALLICENCE 700 1- Savelyev E. Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia aut NATIONALLICENCE 700 1- Orlinson B. Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia aut NATIONALLICENCE 700 1- Novakov I. Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia aut NATIONALLICENCE 700 1- Beletskaya I. Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/3(2015-03-01), 301-308 1070-4280 51:3<301 2015 51 11178