1049-08-7Relevant academic research and scientific papers
A green, solvent-free one-pot synthesis of disubstituted quinolines via A3-coupling using 1 mol% fecl3
Naidoo, Shivani,Jeena, Vineet
, p. 1655 - 1664 (2016)
A simple and green route towards disubstituted quinolines via A3-coupling using 1 mol% FeCl3 is described. Using this approach, the above-mentioned derivatives were synthesized in moderate to good yields (45-95%) under solvent-free, microwave conditions. Preliminary investigations have indicated that a further decrease in catalyst amount is possible with a satisfactory yield still observed.
Ytterbium pentafluorobenzoate as a novel fluorous Lewis acid catalyst in the synthesis of 2,4-disubstituted quinolines
Tang, Jun,Wang, Limin,Mao, Dan,Wang, Wenbo,Zhang, Liang,Wu, Shengying,Xie, Yongshu
, p. 8465 - 8469 (2011)
A series of simple, efficient, stable and recoverable rare earth metal pentafluorobenzoates [RE(Pfb)3] have been synthesized for the first time. A highly efficient and environmentally friendly synthesis of 2,4-disubstituted quinolines catalyzed by Yb(Pfb)3 via one-pot reaction of aldehydes, alkynes and amines under solvent-free conditions has been explored.
Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Br?nsted acidic ionic liquid
Gajare, Shivanand,Patil, Audumbar,Hangirgekar, Shankar,Dhanmane, Sushilkumar,Rashinkar, Gajanan
, p. 2417 - 2436 (2020)
Abstract: Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS 13C NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer–Emmett–Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A3-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product. Graphic abstract: [Figure not available: see fulltext.].
A novel preparation of 4-phenylquinoline derivatives in ionic liquids
Zhang, Xinying,Fan, Xuesen,Wang, Jianji,Li, Yanzhen
, p. 1339 - 1342 (2004)
A novel preparation of 4-phenylquinoline derivatives through acid-catalyzed Friedlaender reaction in ionic liquid ([bmim][BF4]) is described. The preparative procedure presented in this paper is operationally simple and environmentally benign.
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.
Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines
Bulatov, Evgeny,Helaja, Juho,Hu, Tao,Lenarda, Anna,M?kel?, Mikko K.,Malinen, Kiia,Melchionna, Michele,Nieger, Martin,Talvitie, Juulia,Wirtanen, Tom
, p. 3775 - 3782 (2021/07/20)
Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).
Synthesis of new quinolizinium-based fluorescent compounds and studies on their applications in photocatalysis
Chan, Wing-Cheung,Deng, Jie-Ren,Ko, Ben Chi-Bun,Tantipanjaporn, Ajcharapan,Wong, Man-Kin,Yip, Wai-Ming,Yu, Qiong
supporting information, p. 8507 - 8515 (2021/10/20)
Quinoliziniums, cationic aromatic heterocycles bearing a quaternary bridgehead nitrogen, have been widely used as fluorescent dyes, DNA intercalators, ionic liquidsetc. A library of new quinolizinium compounds was synthesized from quinolines and internal alkyne substrates in up to 65% isolated yields. Systematic studies of their photophysical properties were conducted. The quinoliziniums have been used in three visible-light-induced photocatalysis reactions with good yields.
Green synthesis of trimetallic oxide nanoparticles and their use as an efficient catalyst for the green synthesis of quinoline and spirooxindoles: Antibacterial, cytotoxicity and anti-colon cancer effects
Ali Nasseri, Mohammad,Kazemnejadi, Milad,Keshtkar, Hamideh,Mahmoudi, Boshra,Soleimani, Faezeh
, (2021/09/28)
The three-metallic oxide (Cu/Cr/Ni) nanoparticles were prepared using Echinops persicus plant extract via a simple, biocompatible, cost-effective, and non-toxic procedure, and their catalytic activity was evaluated over the synthesis of biologically activ
Magnetic Fe–Cr–Ni oxide alloy nano-belts prepared from the chemical decomposition of a stainless steel screw (a top-down approach): an efficient and cheap catalyst for multicomponent reactions
Kazemnejadi, Milad,Sharafi, Zeinab,Mahmoudi, Boshra,Zeinali, Atefeh,Nasseri, Mohammad Ali
, p. 777 - 787 (2019/11/21)
Abstract: A new, cheap, and accessible method has been used for the preparation of nano-belts from the chemical decomposition (top-down approach) of a cheap stainless steel screw and found as an efficient magnetically recyclable nanocatalyst for the prepa
MOF-5 as a highly efficient and recyclable catalyst for one pot synthesis of 2,4-disubstituted quinoline derivatives
Di, Jia-Qi,Ma, Cui-Ting,Xiao, Song-Tao,Zhang, Zhan-Hui
, p. 8614 - 8620 (2020/06/09)
A MOF-5-catalyzed three-component coupling reaction was developed as an efficient approach for the synthesis of 2,4-disubstituted quinoline derivatives via a one pot three-component reaction of aromatic amines, aldehydes and alkynes with excellent yields. The easy recovery and reusability of the catalyst, broad substrate scope, short reaction time, high yields of products and solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.
