21923-45-5Relevant articles and documents
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
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.
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.
