97355-56-1

Upstream product

• 122-39-4 diphenylamine 
• 133-08-4 diethyl butylmalonate 
• 67-56-1 methanol 
• 773837-37-9 sodium cyanide 
• 144603-28-1 3-butyl-3-chloro-1-phenyl-1H,3H-quinoline-2,4-dione 

Downstream Products

• 144603-28-1 3-butyl-3-chloro-1-phenyl-1H,3H-quinoline-2,4-dione 
• 186766-15-4 3-Butyl-3-hydroxy-1-phenyl-1H-quinoline-2,4-dione 
• 1432733-32-8 3-butyl-4-chloro-1-phenylquinolin-2-one 
• 1432733-44-2 3-butyl-1,2-dihydro-2-oxo-1-phenylquinolin-4-yl dihydrogen phosphate hydrate 

Relevant academic research and scientific papers

Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones

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

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

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.

Pinacol rearrangement of 3,4-dihydro-3,4-dihydroxyquinolin-2(1H)-ones: An alternative pathway to viridicatin alkaloids and their analogs

3-Alkyl/aryl-3-hydroxyquinoline-2,4-diones were reduced with NaBH 4 to give cis-3-alkyl/aryl-3,4-dihydro-3,4-dihydroxyquinolin-2(1H)- ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SOs

Modified riemschneider reaction of 3-thiocyanatoquinolinediones

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

Novel tandem hydration/cyclodehydration of α-thiocyanatoketones to 2-oxo-3-thiazolines. Application, to thiazolo[5,4-c]quinoline-2}4(3aH,5H)-dione synthesis

Novel tandem hydration of α-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2, 4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).

Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange

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.