14505-86-3Relevant academic research and scientific papers
Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
Talvitie, Juulia,Alanko, Iida,Bulatov, Evgeny,Koivula, Juho,P?ll?nen, Topias,Helaja, Juho
supporting information, p. 274 - 278 (2022/01/04)
Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.
Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids
Ren, Xiaoxiao,Han, Shuaijun,Gao, Xianying,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
, p. 1065 - 1068 (2018/02/19)
A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.
Cu(OAc)2-catalyzed direct radical C2 arylation of quinoline N-oxide with arylamines
Yuan, Jin-Wei,Liu, Shuai-Nan,Qu, Ling-Bo
, p. 2267 - 2275 (2017/03/24)
A Cu(OAc)2-catalyzed synthesis of 2-arylquinoline N-oxides with easily available arylamines is described. The main features of this reaction are mild reaction conditions, high functional-group tolerance, excellent regioselectivity, and good to excellent yields. This procedure is mild, operationally simple, and constitutes a greener approach to the arylation of quinoline N-oxides.
Ytterbium(III) triflate catalyzed synthesis of quinoline derivatives from N-arylaldimines and vinyl ethers
Makioka,Shindo,Taniguchi,Takaki,Fujiwara
, p. 801 - 804 (2007/10/02)
[4 + 2] Cycloaddition reaction of N-arylaldimines with vinyl ethers is effectively catalyzed by ytterbium(III) triflate to give quinoline derivatives in good yields. Furthermore, the reaction with silyl enol ethers affords 4-siloxytetrahydroquinolines, whereas an imino aldol reaction takes place in the reaction with ketene silyl acetals.
A Convenient Synthesis of Substituted Quinolines by Thermal Electrocyclic Rearrangement of o-Vinyl Anils under Nonacidic Conditions
Qiang, Lin Guo,Baine, Neil H.
, p. 4218 - 4222 (2007/10/02)
Anils 8a-g (Table II) underwent smooth rearrangement and oxidation to the quinolines 9a-g at 155-200 deg C via formation of the 2-3 carbon-carbon bond.These cyclizations proceeded in high yields under nonacidic conditions.It was often possible to prepare
