15000-41-6Relevant academic research and scientific papers
4-HYDROXY-2-QUINOLONES. 1. EFFICIENT METHOD FOR OBTAINING 3-ALKYL-4-HYDROXY-2-QUINOLONES
Bezuglyi, P.A.,Ukrainets, I.V.,Treskach, V.I.,Turov, A.V.
, p. 1237 - 1238 (1991)
3-Alkyl-4-hydroxy-2-quinolones were obtained in high yields via the Dieckmann intramolecular condensation of substituted malonic acid ethyl ester 2-carbalkoxyanilides.
Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones
Bedná?, Luká?,Kafka, Stanislav,Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Rudolf, Ond?ej
, p. 645 - 652 (2021/07/22)
3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position
One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline
Menglin, Ma,Qingrong, Sun,Weiqing, Yang,Xingyi, Wang,Yinan, Xu
, p. 435 - 441 (2021/11/22)
3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.
Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones
de Macedo, Maíra Bidart,Kimmel, Roman,Urankar, Damijana,Gazvoda, Martin,Peixoto, Antonio,Cools, Freya,Torfs, Eveline,Verschaeve, Luc,Lima, Emerson Silva,Ly?ka, Antonín,Mili?evi?, David,Klásek, Antonín,Cos, Paul,Kafka, Stanislav,Ko?mrlj, Janez,Cappoen, Davie
, p. 491 - 500 (2017/07/10)
In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.
Stereochemistry of the reduction of α-chloroketones with sodium borohydride—application to 3-chloroquinoline-2,4-diones: Dedicated to the memory of Professor Dr.?Vojeslav ?těrba who died in September 2015 being nearly 93 years old
Klásek, Antonín,Ly?ka, Antonín,K?emen, Filip,Rouchal, Michal
, p. 4490 - 4497 (2016/07/07)
3-Chloroquinoline-2,4-diones were reduced with sodium borohydride to give syn- and anti-chlorohydrins, the stereochemistry of which was established by NMR spectroscopy. Both stereoisomeric chlorohydrins were reacted with potassium carbonate in methanol. a
3-Methylene-2,4-chromandione in situ trapping: Introducing molecular diversity on 4-hydroxycoumarin
Montagut-Romans, Adrien,Boulven, Manon,Lemaire, Marc,Popowycz, Florence
, p. 4540 - 4544 (2016/01/29)
3-Methylene-2,4-chromandione trapped in a solid-state stable Mannich adduct, is released in solution. In the presence of different nucleophiles, this highly reactive intermediate allows the introduction of molecular diversity on C-3 position of 4-hydroxycoumarin.
Reduction of 3-aminoquinoline-2,4(1H,3H)-diones and deamination of the reaction products
Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Rudolf, Ond?ej,R??i?ka, Ale?
, p. 595 - 612 (2014/06/09)
3-Aminoquinoline-2,4-diones were stereoselectively reduced with NaBH 4 to give cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a-dihydrooxazolo[4,5-
Iridium catalysed alkylation of 4-hydroxy coumarin, 4-hydroxy-2-quinolones and quinolin-4(1H)-one with alcohols under solvent free thermal conditions
Grigg, Ronald,Whitney, Simon,Sridharan, Visuvanathar,Keep, Ann,Derrick, Andrew
experimental part, p. 7468 - 7473 (2009/12/04)
Ir catalysed alkylation of 4-hydroxy coumarin, 4-hydroxy-2-quinolones and quinolin-4(1H)-one with a range of substituted benzyl and aliphatic alcohols under solvent free thermal conditions afforded the corresponding monoalkylated products in high to excel
Synthesis of 3-thiocyanato-1H,3H-quinoline-2,4-diones
Klasek, Antonin,Polis, Jiri,Mrkvicka, Vladimir,Kosmrlj, Janez
, p. 1315 - 1320 (2007/10/03)
4-Hydroxy-1H-quinolin-2-ones (1) react with thiocyanogen in acetic acid to the corresponding 3-thiocyanato-1H,3H-quinoline-2,4-diones (2) in good yields. In some cases, 3-bromo-1H,3H-quinoline-2,4-diones (4) were isolated as minor reaction products. Compo
Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones
Kafka, Stanislav,Klásek, Antonín,Polis, Ji?í,Ko?mrlj, Janez
, p. 1659 - 1682 (2007/10/03)
Reaction of 3-chloro- (2) and 3-bromoquinoline-2,4(1H,3H)-diones (3) with excess of primary alkyl- or arylamines in dimethylformamide provides the corresponding 3-alkyl- or 3-arylamino derivatives (4). Compounds (4) with the primary amino group at the 3 position were best prepared by reaction of 2 with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines (4) via reduction of 3-azidoquinoline-2,4(1H,3H)-diones (5) was investigated. The reduction of 5 with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphine afforded exclusively 4-hydroxyquinolin-2(1H)-one (1).
