128564-87-4Relevant academic research and scientific papers
Synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones ?
Mili?evi?, David,Kimmel, Roman,Gazvoda, Martin,Urankar, Damijana,Kafka, Stanislav,Ko?mrlj, Janez
, (2018/09/14)
Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title
Copper(I)-catalyzed [3+2] cycloaddition of 3-azidoquinoline-2,4(1H,3H)- diones with terminal alkynes
Kafka, Stanislav,Hauke, Sylvia,Salcinovic, Arjana,Soidinsalo, Otto,Urankar, Damijana,Kosmrlj, Janez
, p. 4070 - 4081 (2011/07/30)
3-Azidoquinoline-2,4(1H,3H)-diones 1,which are readily available from 4-hydroxyquinolin-2(1H)-ones 4 via 3-chloroquinoline-2,4(1H,3H)-diones 5, afford, in copper(I)-catalyzed [3+2] cycloaddition reaction with terminal acetylenes, 1,4-disubstituted 1,2,3-t
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).
Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange
Stadlbauer, Wolfgang,Laschober, Rita,Lutschounig, Herbert,Schindler, Gerda,Kappe, Thomas
, p. 617 - 636 (2007/10/02)
3-Substituted 4-hydroxy-2(1H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10.Reactions of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11.Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13.Similarly the dichloro quinolinediones 10an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.Keywords.Fluorination; 4-Hydroxy-2(1H)-quinolones, 3-alkyl/3-aryl/3-fluoro; 1-Hydroxy-benzoquinolizine-3-ones, 2-alkyl/3-aryl; Quinoline-2,4(1H,3H)-diones, 3-azido-3-alkyl/3-aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro.
