477950-28-0

Upstream product

• 758640-21-0 N-Benzylaniline 
• 83-13-6 diethyl 2-phenylmalonate 
• 477950-26-8 1-benzyl-4-hydroxy-3-phenyl-1,2-dihydroquinolin-2-one 

Downstream Products

• 1303613-95-7 1-benzyl-3-phenyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione 
• 1303613-96-8 1-benzyl-3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-3-phenylquinoline-2,4(1H,3H)-dione 
• 477950-22-4 1-benzyl-3-butylamino-3-phenylquinoline-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

Copper(I)-catalyzed [3+2] cycloaddition of 3-azidoquinoline-2,4(1H,3H)- diones with terminal alkynes

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

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).