57625-53-3Relevant academic research and scientific papers
A simple and effective method for the reduction of acyl substituted heterocyclic 1,3-dicarbonyl compounds to alkyl derivatives by zinc - acetic acid - hydrochloric acid
Kappe, Thomas,Aigner, Rudolf,Roschger, Peter,Schnell, Barbara,Stadlbauer, Wolfgang
, p. 12923 - 12928 (2007/10/02)
3-Acyl-4-hydroxy-2(1H)-quinolones (1a-k) were reduced in good yields (66-97%) to 3-alkyl-4-hydroxy-2(1H)-quinolinones (2a-k) using zinc powder (particle size 〈45 μm) in acetic acid/hydrochloric acid. This method could be transformed to 3-acetyl-4-hydroxy-
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.
