Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition
Vera A. Vil’
1
,
Sergei S Grishin
1, 2
,
Elena P Baberkina
2
,
Anna L Alekseenko
1, 2
,
Alexey P Glinushkin
3
,
Alexey E Kovalenko
2
,
Alexander O. Terent’ev
1, 2
Publication type: Journal Article
Publication date: 2022-01-20
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract
Electrochemical synthesis of cyclic ether‐annulated tetrahydroquinolines from imines and cyclic ethers in an undivided cell under constant current conditions was developed. The electrosynthesis proceeds via the enol ether formation from ethers following the aza‐Diels‐Alder [4+2] cycloaddition. The method is applicable to a wide range of imines and results in the desired products in yields of 23 to 75%. In situ preparation of imines from the corresponding anilines and aldehydes led to mostly the same yields of tetrahydroquinolines. No cycloaddition products were formed using the chemical oxidants. Synthesized cyclic ether‐annulated tetrahydroquinolines exhibit high antifungal activity, which is superior to the commercial fungicide Triadimefon.
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15
Total citations:
15
Citations from 2024:
8
(53%)
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MLA
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GOST
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Vil’ V. A. et al. Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 6. pp. 1098-1108.
GOST all authors (up to 50)
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Vil’ V. A., Grishin S. S., Baberkina E. P., Alekseenko A. L., Glinushkin A. P., Kovalenko A. E., Terent’ev A. O. Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 6. pp. 1098-1108.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/adsc.202101355
UR - https://doi.org/10.1002/adsc.202101355
TI - Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition
T2 - Advanced Synthesis and Catalysis
AU - Vil’, Vera A.
AU - Grishin, Sergei S
AU - Baberkina, Elena P
AU - Alekseenko, Anna L
AU - Glinushkin, Alexey P
AU - Kovalenko, Alexey E
AU - Terent’ev, Alexander O.
PY - 2022
DA - 2022/01/20
PB - Wiley
SP - 1098-1108
IS - 6
VL - 364
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Vil’,
author = {Vera A. Vil’ and Sergei S Grishin and Elena P Baberkina and Anna L Alekseenko and Alexey P Glinushkin and Alexey E Kovalenko and Alexander O. Terent’ev},
title = {Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition},
journal = {Advanced Synthesis and Catalysis},
year = {2022},
volume = {364},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/adsc.202101355},
number = {6},
pages = {1098--1108},
doi = {10.1002/adsc.202101355}
}
Cite this
MLA
Copy
Vil’, Vera A., et al. “Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition.” Advanced Synthesis and Catalysis, vol. 364, no. 6, Jan. 2022, pp. 1098-1108. https://doi.org/10.1002/adsc.202101355.
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