79046-05-2Relevant academic research and scientific papers
Environmentally Friendly Nafion-Mediated Friedl?nder Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones
Chan, Chieh-Kai,Lai, Chien-Yu,Wang, Cheng-Chung
, p. 1779 - 1794 (2020/06/08)
An efficient and eco-friendly synthetic route for Friedl?nder quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired quinolines in good to excellent yields. Some structures were confirmed by single-crystal X-ray diffraction analysis.
Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation
Gisbert, Patricia,Albert-Soriano, María,Pastor, Isidro M.
, p. 4928 - 4940 (2019/08/12)
Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14–23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.
Friedlaender synthesis of polysubstituted quinolines and naphthyridines promoted by propylphosphonic anhydride (T3P) under mild conditions
Jida, Mouhamad,Deprez, Benoit
supporting information; experimental part, p. 869 - 873 (2012/07/03)
A new convenient, efficient and environmentally eco-friendly protocol for Friedlaender synthesis of polysubstituted quinolines and naphthyridines is described. A wide variety of new products were readily prepared in the presence of propylphosphonic anhydride (T3P) in short reaction times and excellent yields under mild conditions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
The first cerium (IV) ammonium nitrate (CAN)-catalyzed friedlaender synthesis of quinolines in ionic liquid
Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Du, Hau-Dung,Chenc, Ling-Ching
experimental part, p. 689 - 698 (2010/09/07)
A mild and efficient route for the synthesis of quinolines and polycyclic quinolines utilizing cerium (IV) ammonium nitrate (CAN) as a novel catalyst via Friedlaender annulation in ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate [Bmim][PF6]
Gd(OTf)3-[Bmim][PF6]: A novel and recyclable catalytic system for the synthesis of quinolines
Wu, Jian-Long,Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Chen, Ling-Ching
experimental part, p. 867 - 872 (2010/08/13)
A mild and efficient route for the synthesis of quinolines and polycyclic quinolines utilizing Gadolinium triflate (Gd(OTf)3) as a novel catalyst via Friedlaender annulation in ionic liquid 1-n-butyl-3- methylimidazolium hexafluorophosphate [Bm
An efficient protocol for the Friedlaender quinoline synthesis using the Lewis acidic ionic liquid choline chloride · 2ZnCl2
Wang, Huey-Min,Hou, Rei-Sheu,Cheng, Hui-Ting,Chen, Ling-Ching
experimental part, p. 487 - 493 (2009/05/31)
Lewis acidic ionic liquid choline chloride · 2ZnCl2 is shown to be for the first time an excellent solvent and efficient catalyst for the synthesis of quinolines via Friedlaender annulation under mild conditions.
Green Protocol for the Friedlaender Synthesis: KAL(SO4)2·12H2O-SiO2 (ALUM-SiO2) A Highly Efficient Catalyst in the Synthesis of Quinolines
Mohammadi, Ali A.,Azizian, Javad,Hadadzahmatkesh, Armin,Asghariganjeh, Mohammad R.
, p. 947 - 954 (2008/09/21)
In this letter, an efficient synthesis of an array of poly-substituted quinolines from 2-aminoaryl ketones and β-ketoester, β-diketones and α-methylene ketones using KAl(SO4)2·12H2O-SiO2 (Alum-SiO2) u
Ionic Liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines
Palimkar, Sanjay S.,Siddiqui, Shapi A.,Daniel, Thomas,Lahoti, Rajgopal J.,Srinivasan, Kumar V.
, p. 9371 - 9378 (2007/10/03)
Several room-temperature ionic liquids (ILs) based on 1-butylimidazolium salts with varying anions were synthesized and evaluated for the preparation of biologically active substituted quinolines and fused polycyclic quinolines using the Friedlander heter
Preparation of 2,4-Diarylquinolines and Substituted Dihydrobenzacridines by the Condensation of Certain C(α),O-Dilithiooximes with 2-Aminobenzophenones
Park, Dorothy J.,Fulmer, Tammy D.,Beam, Charles F.
, p. 649 - 652 (2007/10/02)
C(α),O-Dilithiooximes were prepared in an excess of lithium diisopropylamide and condensed with several 2-aminobenzophenones, followed by acid hydrolysis of the oximes to the ketones, which then underwent cyclodehydration to give substituted quinolines or dihydrobenzacridines.
