63352-82-9Relevant academic research and scientific papers
Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
Xiang, Yunyu,Luo, Puying,Hao, Tianxin,Xiong, Weikang,Song, Xiaolin,Ding, Qiuping
, (2020/12/13)
A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.
DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles
Cai, Hu,Tan, Wei,Xie, Yongfa,Yang, Ruchun,Yue, Shusheng
, p. 7501 - 7509 (2020/07/07)
Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.
Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines
Yuan, Jin,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
, p. 1334 - 1337 (2017/02/15)
A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.
A new synthesis of 4-phenylquinolines by reaction of 2-(α-bromobenzyl)oxiranes with aniline derivatives
Karikomi, Michinori,Tsukada, Hiroshi,Toda, Takashi
, p. 1249 - 1252 (2007/10/03)
Several 4-phenylquinoline derivatives were synthesized by reaction of (2R*,1′R*)-2-(α-bromobenzyl)oxiranes (1a) with aniline derivatives, and the following treatment of the formed 3-hydroxy-4-phenyl-1,2,3,4-tetrahydroquinolines (2) with the Rydon reagent, and potassium t-butoxide and air oxidation.
Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides
Ali,McKillop,Mitchell,Rebelo,Wallbank
, p. 8117 - 8126 (2007/10/02)
The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of π-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.
