Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid
Publication type: Journal Article
Publication date: 2020-07-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
1-[2-(Adamantan-1-yl)-2-hydroxyethyl]-1,2,3,6-tetrahydropyridines were obtained by reduction of 1-[(adamantan-1-yl)-2-oxoethyl]-pyridinium bromides. By the action of trifluoromethanesulfonic acid, they undergo carbocationic intramolecular cyclization accompanied by the Wagner–Meerwein rearrangement with the formation of substituted 1-azabicyclo[3.3.1]non-3-enes annulated with the homoadamantane framework. The structure of the obtained compounds was confirmed by spectral methods and X-ray structural analysis.
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Shadrikova V. А. et al. Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid // Chemistry of Heterocyclic Compounds. 2020. Vol. 56. No. 7. pp. 898-908.
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Shadrikova V. А., Golovin E. V., Rybakov V. B., Klimochkin Y. N. Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid // Chemistry of Heterocyclic Compounds. 2020. Vol. 56. No. 7. pp. 898-908.
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RIS
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TY - JOUR
DO - 10.1007/s10593-020-02747-9
UR - https://doi.org/10.1007/s10593-020-02747-9
TI - Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid
T2 - Chemistry of Heterocyclic Compounds
AU - Shadrikova, Vera А
AU - Golovin, Evgeny V
AU - Rybakov, Victor B.
AU - Klimochkin, Yuri N.
PY - 2020
DA - 2020/07/01
PB - Springer Nature
SP - 898-908
IS - 7
VL - 56
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2020_Shadrikova,
author = {Vera А Shadrikova and Evgeny V Golovin and Victor B. Rybakov and Yuri N. Klimochkin},
title = {Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid},
journal = {Chemistry of Heterocyclic Compounds},
year = {2020},
volume = {56},
publisher = {Springer Nature},
month = {jul},
url = {https://doi.org/10.1007/s10593-020-02747-9},
number = {7},
pages = {898--908},
doi = {10.1007/s10593-020-02747-9}
}
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MLA
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Shadrikova, Vera А., et al. “Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid.” Chemistry of Heterocyclic Compounds, vol. 56, no. 7, Jul. 2020, pp. 898-908. https://doi.org/10.1007/s10593-020-02747-9.