477950-01-9Relevant academic research and scientific papers
Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones
Kafka, Stanislav,Klásek, Antonín,Polis, Ji?í,Ko?mrlj, Janez
, p. 1659 - 1682 (2007/10/03)
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).
