Amination of chloro-substituted heteroarenes with adamantane-containing amines
- Authors: Abel A.S.1, Grigorova O.K.1, Averin A.D.1, Maloshitskaya O.A.1, Butov G.M.2, Savelyev E.N.3, Orlinson B.S.3, Novakov I.A.3, Beletskaya I.P.1
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Volzhsky Polytechnical Institute (branch) of the Volgograd State Technical University
- Volgograd State Technical University
- Issue: Vol 65, No 7 (2016)
- Pages: 1820-1828
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238602
- DOI: https://doi.org/10.1007/s11172-016-1516-7
- ID: 238602
Cite item
Abstract
Amination of 3,6-dichloropyridazine, chloropyrazine, 2,3and 2,6-dichloropyrazines, 2-chloroquinoxaline, 1-chloroand 1,3-dichloroisoquinolines with various adamantane-containing amines characterized by different steric hindrances at the amino group was studied. The yields of the amination products depended on the structure of starting compounds. In the reactions of all the dichloroheteroarenes, selective substitution of only one chlorine atom took place, with the best yields being observed for 2,6-dichloropyrazine. In the reaction of 1,3-dichloroisoquinoline, the chlorine atom at position 1 was selectively substituted in up to 90% yield.
Keywords
About the authors
A. S. Abel
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
O. K. Grigorova
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
A. D. Averin
Department of Chemistry, M. V. Lomonosov Moscow State University
Author for correspondence.
Email: averin@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
O. A. Maloshitskaya
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
G. M. Butov
Volzhsky Polytechnical Institute (branch) of the Volgograd State Technical University
Email: averin@org.chem.msu.ru
Russian Federation, 42a ul. Engel’sa, Volzhsky, Volgograd Region, 404121
E. N. Savelyev
Volgograd State Technical University
Email: averin@org.chem.msu.ru
Russian Federation, 28 prosp. Lenina, Volgograd, 400131
B. S. Orlinson
Volgograd State Technical University
Email: averin@org.chem.msu.ru
Russian Federation, 28 prosp. Lenina, Volgograd, 400131
I. A. Novakov
Volgograd State Technical University
Email: averin@org.chem.msu.ru
Russian Federation, 28 prosp. Lenina, Volgograd, 400131
I. P. Beletskaya
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991