Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines
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| 024 | 7 | 0 | |a 10.1134/S1070428015030021 |2 doi |
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| 245 | 0 | 0 | |a Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines |h [Elektronische Daten] |c [A. Abel, A. Averin, M. Anokhin, O. Maloshitskaya, G. Butov, E. Savelyev, B. Orlinson, I. Novakov, I. Beletskaya] |
| 520 | 3 | |a 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. | |
| 540 | |a Pleiades Publishing, Ltd., 2015 | ||
| 700 | 1 | |a Abel |D A. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | |
| 700 | 1 | |a Averin |D A. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | |
| 700 | 1 | |a Anokhin |D M. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | |
| 700 | 1 | |a Maloshitskaya |D O. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | |
| 700 | 1 | |a Butov |D G. |u Volzhsky Polytechnical Institute, Volgograd State Technical University, ul. Engel'sa 42a, 404130, Volzhskii, Volgograd oblast, Russia |4 aut | |
| 700 | 1 | |a Savelyev |D E. |u Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia |4 aut | |
| 700 | 1 | |a Orlinson |D B. |u Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia |4 aut | |
| 700 | 1 | |a Novakov |D I. |u Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia |4 aut | |
| 700 | 1 | |a Beletskaya |D I. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | |
| 773 | 0 | |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/3(2015-03-01), 301-308 |x 1070-4280 |q 51:3<301 |1 2015 |2 51 |o 11178 | |
| 856 | 4 | 0 | |u https://doi.org/10.1134/S1070428015030021 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1134/S1070428015030021 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Abel |D A. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Averin |D A. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Anokhin |D M. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Maloshitskaya |D O. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Butov |D G. |u Volzhsky Polytechnical Institute, Volgograd State Technical University, ul. Engel'sa 42a, 404130, Volzhskii, Volgograd oblast, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Savelyev |D E. |u Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Orlinson |D B. |u Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Novakov |D I. |u Volgograd State Technical University, pr. Lenina 28, 400005, Volgograd, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Beletskaya |D I. |u Faculty of Chemistry, Moscow State University, Leninskie gory 1, 119991, Moscow, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/3(2015-03-01), 301-308 |x 1070-4280 |q 51:3<301 |1 2015 |2 51 |o 11178 | ||