30160-03-3Relevant articles and documents
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.
Synthesis of quinolines: Via copper-catalyzed domino reactions of enaminones
Kaewmee, Benyapa,Rukachaisirikul, Vatcharin,Kaeobamrung, Juthanat
, p. 7387 - 7395 (2017/09/25)
Quinoline derivatives were obtained from enaminones and 2-bromo- or 2-iodobenzaldehydes via copper-catalyzed domino reactions consisting of the aldol reaction, C(aryl)-N bond formation and elimination. The electronic effect of aldehydes played a major role in the reaction outcome. Two simple protocols are disclosed to achieve various quinolines from both cyclic and acyclic enaminones in good yields. With the less-reactive acyclic enaminones, diethyl-2-(2-bromobenzylidene)malonate was shown to be more compatible than the benzaldehydes.
Quinoline-based p300 histone acetyltransferase inhibitors with Pro-apoptotic activity in human leukemia U937 cells
Lenoci, Alessia,Tomassi, Stefano,Conte, Mariarosaria,Benedetti, Rosaria,Rodriguez, Veronica,Carradori, Simone,Secci, Daniela,Castellano, Sabrina,Sbardella, Gianluca,Filetici, Patrizia,Novellino, Ettore,Altucci, Lucia,Rotili, Dante,Mai, Antonello
supporting information, p. 542 - 548 (2014/03/21)
Chemical manipulations performed on 2-methyl-3-carbethoxyquinoline (1), a histone acetyltransferase inhibitor previously identified by our research group and active at the sub-millimolar/millimolar level, led to compounds bearing higher alkyl groups at th
