893620-09-2Relevant academic research and scientific papers
Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones
Manikandan, Rajendran,Jeganmohan, Masilamani
supporting information, p. 3568 - 3571 (2014/07/21)
A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines
Synthesis and anticonvulsant activity of 5-phenyl-[1,2,4]-triazolo[4,3-a] quinolines
Guan, Li-Ping,Jin, Qing-Hao,Wang, Shou-Feng,Li, Fu-Nan,Quan, Zhe-Shan
scheme or table, p. 774 - 779 (2009/04/14)
A series of novel 5-phenyl-[1,2,4]-triazolo[4,3-a]quinoline derivatives was synthesized by the cyclization of 2-chloro-4-phenyl-1,2-dihydronaphthalene with formohydrazide. The starting material 2-chloro-4-phenyl-1,2-dihydronaphthalene was synthesized from ethyl-3-oxo-3-phenylpropanoate and substituted aniline. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The maximal electroshock test showed that 7-hexyloxy-5-phenyl-[1,2,4]- triazolo[4,3-a]quinoline 4f was found to be the most potent compound with an ED50 value of 6.5 mg/kg and a protective index (PI = ED 50/TD50) value of 35.1, which was much higher than the PI of the reference drug phenytoin.
Long-wavelength-absorbing and -emitting carbostyrils with high fluorescence quantum yields
Uray, Georg,Niederreiter, Karlheinz S.,Belaj, Ferdinand,Fabian, Walter M. F.
, p. 1408 - 1417 (2007/10/03)
Synthesis, absorption and fluorescence spectra, as well as quantum yields of a series of donor-acceptor-substituted carbostyrils (= quinolin- 2(1H)-ones), are reported. Unprecedented strong absorption maxima (ε = 10000-20000) close to the visible spectrum, large Stokes shifts up to 130 nm, and quantum yields up to 0.7 are obtained with derivatives containing donor substituents at C(6) and C(7), and either one Ph substituent at C(3) or one CF3 residue at C(4). For analytical applications in biochemistry and medicine, N(1)-functionalization, or amidoacylation at C(3) in the case of the CF3 derivatives, is possible without a concomitant hypsochromic shift of their absorption and emission maxima. Semiempirical molecular-orbital calculations (AM1 for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption properties of these compounds. The crystal-structure analysis of 6,7-dimethoxy-1-methyl-3- nitro-4-(trifluoromethyl)quinolin-2-(1H)-one (7) (C13H11F3N2O5, monoclinic, P2(l)lc, a=12.372(2), b= 12.154(2), c= 10.119(2)A, β= 112.95(2)°) shows that the NO2 group, squeezed between the CF?3 and the C=O group, is oriented almost perpendicularly (87.8(4)°) to the ring plane. The intramolecular F ··· N distance between the CF3 and the NO2 group is only 2.513(4)A.
