92859-63-7Relevant academic research and scientific papers
4-HYDROXY-2-QUINOLONES. 26. BROMINATION OF 3-SUBSTITUTED 2-OXO-4-HYDROXYQUINOLINES
Ukrainets, I. V.,Taran, S. G.,Evtifeeva, O. A.,Gorokhova, O. V.,Filimonova, N. I.,Turov, A. V.
, p. 176 - 179 (1995)
The bromination of 3-alkyl- and 3-ethoxycarbonyl-2-oxo-4-hydroxyquinolines by molecular bromine gave 3-bromo-3-R-2,4-dioxoquinolines.Under analogous conditions, 1-R-2,4-dioxo-3H-quinoline-3-carboxylic acids from 1-R-3-bromo-2-oxo-4-hydroxyquinolines.The r
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).
