113059-25-9Relevant articles and documents
Synthesis of quinolines: Via copper-catalyzed domino reactions of enaminones
Kaewmee, Benyapa,Rukachaisirikul, Vatcharin,Kaeobamrung, Juthanat
, p. 7387 - 7395 (2017)
Quinoline derivatives were obtained from enaminones and 2-bromo- or 2-iodobenzaldehydes via copper-catalyzed domino reactions consisting of the aldol reaction, C(aryl)-N bond formation and elimination. The electronic effect of aldehydes played a major role in the reaction outcome. Two simple protocols are disclosed to achieve various quinolines from both cyclic and acyclic enaminones in good yields. With the less-reactive acyclic enaminones, diethyl-2-(2-bromobenzylidene)malonate was shown to be more compatible than the benzaldehydes.
Ag(I)-promoted Decarboxylative Annulation of α-Oxocarboxylic Acids with (E)-3-(2-aminophenyl)-1-Phenylprop-2-en-1-ones Toward 3,4-Functionalized Quinolines
Fan, Xiaodong,Wang, Chang,Cheng, Jiang
, p. 777 - 782 (2022/03/01)
An efficient Ag-promoted decarboxylative cyclization of α-oxocarboxylic acids with (E)-3- (2-aminophenyl)-1-phenylprop-2-en-1-ones has been developed to afford a series of functionalized quinolines in moderate to good yields. This method was compatible with a variety of functional groups and provided an attractive method toward phenyl(2-phenylquinolin-3-yl)methanones.
NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
, p. 7772 - 7779 (2021/06/30)
Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
Method for synthesizing quinoline derivatives
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Paragraph 0035-0039, (2019/10/01)
The invention discloses a method for synthesizing quinoline derivatives. 2,1-benzisoxazole derivatives represented by formula I and beta-diketone derivatives represented by formula II are used as rawmaterials, and are reacted to obtain the quinoline deriv