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Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition Full article

Journal Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150
Output data Year: 2022, Volume: 364, Number: 6, Pages: 1098-1108 Pages count : 11 DOI: 10.1002/adsc.202101355
Authors Vil' Vera A. 1 , Grishin Sergei S. 1,2 , Baberkina Elena P. 2 , Alekseenko Anna L. 1,2 , Glinushkin Alexey P. 3 , Kovalenko Alexey E. 2 , Terent'ev Alexander O. 1,2
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences , 47 Leninsky prosp., 119991, Moscow, Russian Federation
2 D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, 125047, Moscow, Russian Federation
3 All-Russian Research Institute for Phytopathology, B. Vyazyomy, 143050, Moscow Region, Russian Federation

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.
Cite: 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 & Catalysis. 2022. V.364. N6. P.1098-1108. DOI: 10.1002/adsc.202101355 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000744679200001
Scopus: 2-s2.0-85123175892
OpenAlex: W4206432847
Citing:
DB Citing
OpenAlex 11
Scopus 10
Web of science 11
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