Open Access
Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines
Anton Abel
1
,
Alexei Averin
1
,
Olga Maloshitskaya
1
,
Evgenii Savelyev
2
,
Boris Orlinson
2
,
Ivan Novakov
2
,
Publication type: Journal Article
Publication date: 2013-02-06
PubMed ID:
23389254
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
Pd-catalyzed amination of isomeric 2,6-, 2,8-, 4,8- and 4,7-dichloroquinolines was studied using adamantane-containing amines in which substituents at the nitrogen atom differ in bulkiness. The selectivity of the amination of 2,6-dichloroquinoline was very low, substantially better results were obtained with 2,8-dichloroquinoline, and 4,8- and 4,7-dichloroquinolines provided the best yields of the amination products. Diamination of 4,8- and 4,7-dichloroquinolines was carried out with two amines which differ strongly in the bulkiness of the alkyl group. In the majority of cases BINAP ligand was successfully applied, however, it had to be replaced with DavePhos in certain reactions when using the most sterically hindered amine as well as for the diamination reactions.
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Abel A. et al. Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines // Molecules. 2013. Vol. 18. No. 2. pp. 2096-2109.
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Abel A., Averin A., Maloshitskaya O., Savelyev E., Orlinson B., Novakov I., Beletskaya I. Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines // Molecules. 2013. Vol. 18. No. 2. pp. 2096-2109.
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RIS
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TY - JOUR
DO - 10.3390/molecules18022096
UR - https://doi.org/10.3390/molecules18022096
TI - Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines
T2 - Molecules
AU - Abel, Anton
AU - Averin, Alexei
AU - Maloshitskaya, Olga
AU - Savelyev, Evgenii
AU - Orlinson, Boris
AU - Novakov, Ivan
AU - Beletskaya, Irina
PY - 2013
DA - 2013/02/06
PB - MDPI
SP - 2096-2109
IS - 2
VL - 18
PMID - 23389254
SN - 1420-3049
ER -
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BibTex (up to 50 authors)
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@article{2013_Abel,
author = {Anton Abel and Alexei Averin and Olga Maloshitskaya and Evgenii Savelyev and Boris Orlinson and Ivan Novakov and Irina Beletskaya},
title = {Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines},
journal = {Molecules},
year = {2013},
volume = {18},
publisher = {MDPI},
month = {feb},
url = {https://doi.org/10.3390/molecules18022096},
number = {2},
pages = {2096--2109},
doi = {10.3390/molecules18022096}
}
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MLA
Copy
Abel, Anton, et al. “Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines.” Molecules, vol. 18, no. 2, Feb. 2013, pp. 2096-2109. https://doi.org/10.3390/molecules18022096.
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