477950-08-6

Upstream product

• 144603-33-8 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 144603-94-1 3-azido-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 401635-58-3 3-bromo-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 519-66-4 4-hydroxy-1-methyl-3-phenylquinolin-2-one 

Downstream Products

• 1161924-67-9 1-methyl-3-phenyl-3-(3'-phenylureido)quinoline-2,4(1H_.3H)-dione 
• 1161924-70-4 3,3a,5,9b-tetrahydro-9b-hydroxy-5-methyl-1,3a-diphenyl-1H-imidazo[4,5-c]quinoline-2,4-dione 
• 1161924-66-8 3-(3'-butylureido)-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 1161924-69-1 1-butyl-3,3a,5,9b-tetrahydro-9b-hydroxy-5-methyl-3a-phenyl-1H-imidazo[4,5-c]quinoline-2,4-dione 
• 113737-84-1 3-hydroxy-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 1300670-39-6 3-(3'-benzoylthioureido)-1-methyl-2-oxo-2,3-dihydro-1H-indole 
• 1220887-15-9 1,5-dimethyl-9b-hydroxy-3a-phenyl-1,2,3,3a,9b-pentahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4-one 
• 1220887-16-0 1,3a-diphenyl-9b-hydroxy-5-methyl-1,2,3,3a,9b-pentahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4-one 
• 1030030-72-8 5-methyl-3a-phenyl-3,3a-dihydro-2H-pyrrolo[2,3-c]quinoline-2,4(5H)-dione 
• 1030030-61-5 (E)-ethyl 2-(3-amino-1-methyl-2-oxo-3-phenyl-2,3-dihydroquinolin-4(1H)-ylidene)acetate 
• 1030030-86-4 2-bromo-N-(1-methyl-2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)acetamide 
• 1030031-01-6 N-(1-methyl-2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)acetamide 

Relevant academic research and scientific papers

Reaction of 3-phenyl-3-aminoquinoline-2,4-diones with isothiocyanates. Facile access to novel spiro-linked 2-thioxoimidazolidine-oxindoles and imidazoline-2-thiones

3-Phenyl-3-amino-1H,3H-quinoline-2,4-diones (1) react with alkyl or aryl isothiocyanates to give novel 9b-hydroxy-3a-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-ones in high yields. These compounds rearrange in boiling acetic acid

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).