174840-94-9Relevant academic research and scientific papers
2-Aryl-3-hydroxyquinolones, a new class of dyes with solvent dependent dual emission due to excited state intramolecular proton transfer
Yushchenko, Dmytro A.,Shvadchak, Volodymyr V.,Klymchenko, Andrey S.,Duportail, Guy,Mely, Yves,Pivovarenko, Vasyl G.
, p. 774 - 781 (2007/10/03)
Herein, the fluorescence properties of a series of 2-aryl-3- hydroxyquinolones (3HQs) were investigated and compared with the properties of well-studied 3-hydroxyflavone. All these compounds were found to display dual fluorescence with well-separated band
Preparation of 1,2-disubstituted-3-hydroxy-4(1H)-quinolinones and the influence of substitution on the course of cyclization
Hradil, Pavel,Hlavac, Jan,Lemr, Karel
, p. 141 - 144 (2007/10/03)
Synthesis of 1,2-disubstituted-3-hydroxy-4(1H)-quinolinones by the cyclization of N-substituted phenacyl or acetonyl anthranilates is described. Two methods were employed for cyclization of anthranilates. Heating in polyphosphoric acid has a wide scope of applicability. The thermal cyclization in boiling N-methylpyrrolidone is limited by steric effect.
Ring closing and photooxidation in nitrogen analogues of 3-hydroxyflavone
Gao, Feng,Johnson, Kurtis F.,Schlenoff, Joseph B.
, p. 269 - 274 (2007/10/03)
An epoxide intermediate in the Algar-Flynn-Oyamada (AFO) synthesis of flavones is reaffirmed through the use of quinolone analogues to 3-hydroxyflavone (3HF).Stepwise synthesis of analogues 3-hydroxy-2-phenyl-1,4-dihydro-4-quinolone 11 and 3-hydroxy-1-methyl-2-phenyl-1,4-dihydro-4-quinolone 12, via chalcone formation, epoxidation, ring closing and final oxidation, has been accomplished.The intermediacy of an epoxide is further supported by blocking cyclization with methoxy substitution at the 2'-position (1A).Absorption/emission spectroscopy of 11 and 12 shows large red shifts, as seen in 3HF, indicative of an excited state intramolecular proton transfer mechanism.Nitrogen analogues demonstrate photooxidative stability similar to that of 3HF.
