21923-45-5Relevant academic research and scientific papers
Synthesis and trypanocidal activity of substituted 2,4-diarylquinoline derivatives
Oluwafemi, Kola A.,Phunguphungu, Siyolise,Gqunu, Sinalo,Isaacs, Michelle,Hoppe, Heinrich C.,Klein, Rosalyn,Kaye, Perry T.
, (2021/06/17)
A small library of nine, novel 2,4-diarylquinoline derivatives has been prepared in high yield via convenient one-or two-step routes from a series of substituted 2-Aminobenzophenones. None of the products exhibited toxicity at 20 uM against human cervix a
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
A facile one-pot synthesis of substituted quinolines via cascade friedlander reaction from isoxazoles with ammonium formate-PD/C and ketones
Chen, Da,Wang, Xuan,Wang, Runnan,Zhan, Yao,Peng, Xiaohan,Xia, Tian,Zhang, Zhenming,Li, Runlai,Li, Shu’An
, p. 211 - 215 (2020/02/29)
The Friedlander reaction is the most commonly used method to synthesis substituted quinolines, the essential intermediates in the medicine industry. A facile one-pot approach for synthesizing substituted quinolines by the reaction of isoxazoles, ammonium formate-Pd/C, concentrated sulfuric acid, methanol and ketones using Friedlander reaction conditions is reported. Procedures for the synthesis of quinoline derivatives were optimized, and the yield was up to 90.4%. The yield of aromatic ketones bearing electron-withdrawing groups was better than the ones with electron-donating substitu-ents. The structures of eight substituted quinolines were characterized by MS, IR, H-NMR and13CNMR, which were in agreement with the expected structures. The mechanism for the conversion was proposed, which involved the Pd/C catalytic hydrogen transfer reduction of unsaturated five-membered ring of isoxazole to produce ortho-amino aromatic ketones. Then the nucleophilic addition of with car-bonyl of the ketones generated Schiff base in situ, which underwent an intermolecular aldol reaction followed by the elimination of H2O to give production of substituted quinolines. This new strategy can be readily applied for the construction of quinolines utilizing a diverse range of ketones and avoids the post-reaction separation of the o-amino aromatic ketone compounds. The conventionally used o-amino aromatic ketone compounds in Friedlander reaction to prepare substituted quinoline are laborious to synthesize and are apt to self-polymerize. While oxazole adopted in this work can be prepared at ease by the condensation of benzoacetonitrile and nitrobenzene derivatives under the catalysis of a strong base. Moreover, the key features of this protocol are readily available starting materials, excellent functional group tolerance, mild reaction conditions, operational simplicity, and feasibility for scaling up.
Manganese(ii)-catalysed dehydrogenative annulation involving C-C bond formation: highly regioselective synthesis of quinolines
Wang, Chengniu,Yang, Jinfei,Meng, Xiao,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei
supporting information, p. 4474 - 4478 (2019/04/05)
An inexpensive nontoxic manganese(ii)-catalysed dehydrogenative annulation was developed for C-C bond formation. The reaction showed high selectivity and efficiency across a broad substrate scope. Remarkably simple conditions and the ability to conduct gram-scale synthesis underscore this method's utility. To demonstrate the potential of this approach, we tested the drug effects of compound 3n, which showed activity for blocking vascular development. The results of this study will be important for the treatment of eye diseases and tumors caused by vascular proliferation.
Zn(OTf)2-mediated C[sbnd]H activation: An expeditious and solvent-free synthesis of aryl/alkyl substituted quinolines
Sarode, Prashant B.,Bahekar, Sandeep P.,Chandak, Hemant S.
supporting information, p. 5753 - 5756 (2016/12/06)
Zinc(II) triflate catalyzed three-component coupling reactions of alkynes, amines and aldehydes leading to the formation of aryl/alkyl substituted quinolines has been described. Notably, the reaction proceeded efficiently and effectively without the use of ligand, co-catalyst, solvent or inert atmosphere. This robust solvent-free process operates under an ambient atmosphere and avoids the use of precious metals, hazardous solvents and harsh reaction conditions. This atom economic process eliminates the waste generated in the multistep synthesis. Additionally, a pseudo three-component Povarov reaction of amines and butanal proceeds under the same green conditions enabling the formation of 2,3-dialkyl quinolines.
PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives
Nasseri,Alavi,Zakerinasab
, p. 109 - 116 (2013/05/09)
A convenient and efficient method was developed for the synthesis of quinolines, an important class of potentially bioactive compounds. The quinoline derivatives were prepared in water, an excellent solvent in terms of environmental impact and with reduce
Catalyst free indirect Friedlaender synthesis of substituted quinolines from alcohols in PEG-400
Wu, Fang-Wen,Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Chen, Ling-Ching
experimental part, p. 535 - 539 (2012/07/14)
The synthesis of substituted quinolines can be easily and greenly accomplished by the direct reaction between the corresponding aminoalcohol and ketone using PEG-400 as reaction medium in the presence of a base, without any transition-metal catalyst.
Dowex-50w promoted friedlaender synthesis of substituted quinolines under solvent-free conditions
Wang, Huey-Min,Hou, Rei-Sheu,Du, Hau-Dung,Kang, Iou-Jiun,Chen, Ling-Ching
experimental part, p. 331 - 338 (2011/04/15)
An efficient method for the synthesis of substituted quinolines using Dowex-50W ion exchange resin as reusable eco-friendly catalyst vai Friedlaender annulation under solvent-free conditions is described. The Japan Institute of Heterocyclic Chemistry.
Fast, solvent-free, microwave-promoted friedlaender annulation with a reusable solid catalyst
Garella, Davide,Barge, Alessandro,Upadhyaya, Dharita,Rodriguez, Zalua,Palmisano, Giovanni,Cravotto, Giancarlo
experimental part, p. 120 - 128 (2010/03/24)
A fast, solvent-free method is described for the synthesis of substituted quinoline derivatives via Friedlander cyclization, employing a reusable solid catalyst (silica-propylsulfonic acid). Although it worked best under microwave irradiation (with generally more than 90% isolated yields in 30min), the reaction was also feasible under conventional heating (with fair to good yields in about 5h).
Preparation of 2-arninpbenzophenones and polysubstituted quinolines through Sml2 promoted reductive cleavage of 3-aryl-2,1-benzisoxazoles
Fan, Xuesen,Zhang, Xinying,Zhang, Yongmin
, p. 637 - 643 (2007/10/03)
Promoted by SmI2, 3-aryl-2,1-benzisoxazoles underwent reductive cleavage of the N - O bond leading to 2-aminobenzophenones in high yields upon protonation. Otherwise, if ketones with active methylene group were added to the reaction mixture prior to protonation, the desired poly substituted quinolines could be obtained under mild conditions in a one-pot manner.
