1039-51-6Relevant articles and documents
An efficient synthesis of substituted quinolines via indium(III) chloride catalyzed reaction of imines with alkynes
Zhu, Mei,Fu, Weijun,Xun, Chen,Zou, Guanglong
, p. 43 - 47 (2012)
An efficient synthetic method for the preparation of quinolines through indium(III) chloride-catalyzed tandem addition-cyclization-oxidation reactions of imines with alkynes was developed. The processes can provide a diverse range of quinoline derivatives
Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
, p. 10747 - 10754 (2021)
This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
Synthesis of substituted 1,2-dihydroquinolines and quinolines from aromatic amines and alkynes by gold(I)-catalyzed tandem hydroamination-hydroarylation under microwave-assisted conditions
Liu, Xin-Yuan,Ding, Pan,Huang, Jie-Sheng,Che, Chi-Ming
, p. 2645 - 2648 (2007)
Equation Presented A method to efficiently prepare substituted 1,2-dihydroquinolines and quinolines by Au(I)-catalyzed tandem hydroamination-hydroarylation under microwave irradiation was developed. This method requires short reaction time (10-70 min) and
Divergent Functionalization of N-Alkyl-2-alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines
Ghorai, Jayanta,Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
, p. 2499 - 2504 (2018)
An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C?H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.
N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature
Xu, Jingxiu,Chen, Qingmao,Luo, Zhigao,Tang, Xiaodong,Zhao, Jinwu
, p. 28764 - 28767 (2019)
A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedl?nder reaction from 2-aminobenzyl alcohol and aryl ketones using DMSO as an oxidant at room temperature is reported. A series of quinolines were synthesized in acceptable yields.
Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
, p. 688 - 694 (2020)
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
Copper(I)- And gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N-Aryl-2-propynylamines
Kuninobu, Yoichiro,Inoue, Yuichi,Takai, Kazuhiko
, p. 1422 - 1423 (2007)
2,4-Disubstituted quinoline derivatives were obtained from N-aryl-2-propynylamines catalyzed by copper(I) and gold(I) complexes. The quinoline derivatives could also be obtained by the reaction of N-arylaldimines with terminal acetylenes via the formation of N-aryl-2-propynylamines. Copyright
Metal-Free Synthesis of 2-Substituted Quinolines via High Chemoselective Domino Condensation/Aza-Prins Cyclization/Retro-Aldol between 2-Alkenylanilines with β-Ketoesters
Nan, Jiang,Chen, Pu,Zhang, Yuxin,Yin, Yun,Wang, Bo,Ma, Yangmin
, p. 14042 - 14054 (2020)
A highly chemoselective domino condensation/aza-Prins cyclization/retro-aldol between 2-alkenylanilines with β-dicarbonyl compounds under metal-free conditions was accomplished, giving a large category of valuable 2-substituted quinolines in good yields with excellent functional group toleration. This newly established process, adopting β-ketoesters as masked C1 synthons via C-C cleavage, could even be simplified into a three-component [3 + 2 + 1] domino version consisting of exceedingly low-priced commercial starting materials. The synthetic application of products was exemplified by several intriguing chemical operations.
Synthesis of quinolines via acceptorless dehydrogenative tandem cyclization of 2-amionbenzyl alcohol with alcohols using magnetic CuNiFeO nanocatalyst
Chaurasia, Shivkumar R.,Tiwari, Abhishek R.,Bhanage, Bhalchandra M.
, (2019)
This work reports the preparation of nano CuNiFeO and its application in the synthesis of quinolines. The prepared nanocatalyst was characterized using various characterization techniques such as XRD, FEG-SEM, EDX, HR-TEM and XPS. Nano CuNiFeO as a heterogeneous catalyst shows a very high efficiency towards double dehydrogenation tandem cyclization reaction of 2-amionbenzyl alcohol with alcohols resulting into a simple, sustainable and environment friendly synthesis of quinolines. Due to the magnetic property associated with nanocatalyst, it was easily separated from the reaction mixture using external magnet and could be reused up to five cycles. To the best of our knowledge, this is for the first time a heterogenous magnetic CuNiFeO nanocatalyst is being reported for this reaction.
Silver-catalyzed cascade reaction of o-aminoaryl compounds with alkynes: An aniline mediated synthesis of 2-substituted quinolines
Li, Hongfeng,Wang, Chengyu,Huang, He,Xu, Xiaolei,Li, Yanzhong
, p. 1108 - 1111 (2011)
An efficient silver-catalyzed, aniline mediated cascade hydroamination/cycloaddition of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones with alkynes for the synthesis of 2- or 2,4-substituted quinolines is reported. The reactions proceed with high regioselectivity to afford mono- or disubstituted quinoline derivatives in good to high yields using AgOTf as the catalyst in the air.
