42731-96-4Relevant articles and documents
Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
Rahul,Nitha,Omanakuttan, Vishnu K.,Babu, Sheba Ann,Sasikumar,Praveen, Vakayil K.,Hopf, Henning,John, Jubi
, p. 3081 - 3089 (2020/05/08)
A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
Novel formation of oxazepino[4,5-a]quinolines by tandem 1,3-dipolar and insertion reaction of quinoline N-oxides with arynes
Okuma, Kentaro,Hirano, Koki,Shioga, Chisato,Nagahora, Noriyoshi,Shioji, Kosei
, p. 615 - 619 (2013/07/27)
By combination of 1,3-dipolar cycloaddition and N-O single bond insertion, tandem synthesis of dibenzo[1,4]-oxazepino[4,5-a]quinolines was accomplished. Reaction of quinoline N-oxides with arynes afforded 2-(2-hydroxyphenyl) quinolines and 7-membered pentacyclic oxazepino[4,5-a]quinolines.
Synthesis, characterization and photoluminescence properties of strong fluorescent BF2 complexes bearing (2-quinolin-2-yl)phenol ligands
Ma, Ru-Zheng,Yao, Qi-Chao,Yang, Xi,Xia, Min
scheme or table, p. 93 - 98 (2012/05/19)
Novel N,O bidentate BF2 complexes were prepared in good to excellent yields through the coordination of (2-quinolin-2-yl)phenol and its derivatives with boron trifluoride etherate under mild conditions. These fluorine-boron complexes exhibited strong fluorescence both in organic solvents and in solid state. Their photophysical properties were thoroughly studied by absorption and fluorescence spectroscopy in various solvents. The electronic and site effects of substituents on phenolic and quinolinyl rings were found to have a profound impact on quantum yields. All these complexes were fully characterized by IR, 1H, 13C, 19F NMR and microanalysis. The high quantum yields and large Stokes shifts make these compounds as potential fluorescent dyes.
