1614221-53-2Relevant academic research and scientific papers
2,2,2-trifluoroethanol-promoted access to symmetrically 3,3-disubstituted quinoline-2,4-diones
Abram, Ulrich,Larghi, Enrique L.,Ledesma, Gabriela N.,Morel, Ademir Farias,Schulz-Lang, Ernesto,Selvero, Marcel Manke
, (2020/04/21)
The unprecedented use of 2,2,2-trifluoroethanol as reaction solvent provided a facile and convenient access to symmetrically 3,3-disubstitued quinoline-2,4-diones in moderate to excellent yields and high regioselectivity, by reaction of 4-hydroxy-2-quinolones with electrophiles like methyl iodide, as well as benzyl and allyl bromides in the presence of K2CO3. Silver (I) oxide is required to increase the yield of the methylations.
Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro- 1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity
Ferretti, Matías D.,Neto, Alexandre T.,Morel, Ademir F.,Kaufman, Teodoro S.,Larghi, Enrique L.
, p. 253 - 266 (2014/06/09)
A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4- dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity.
