14944-99-1Relevant academic research and scientific papers
Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday
Kafka, Stanislav,Proisl, Karel,Ka?párková, Věra,Urankar, Damijana,Kimmel, Roman,Ko?mrlj, Janez
, p. 10826 - 10835 (2014/01/06)
N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is
Modified riemschneider reaction of 3-thiocyanatoquinolinediones
Rudolf, Ondrej,Mrkvicka, Vladimir,Lycka, Antonin,Rouchal, Michal,Klasek, Antonin
experimental part, p. 1352 - 1372 (2012/09/25)
The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright
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-
Methods for the Synthesis of 4-Azido-2(1H)-quinolones
Stadlbauer, Wolfgang
, p. 1305 - 1324 (2007/10/02)
4-Hydroxy-2-quinolones 1 are generally found to be converted to the 4-azidocompounds 3 via the 4-chloroquinolones 2, the 4-tosyloxyquinolones 6, or the 4-aminoquinolones 4, respectively.Choice of the reaction conditions and yields depend on the substituen
