Abstract: 3-Substituted 4-hydroxy-2(1H)-quinolones were halogenated with bromine
or sulfuryl chloride to yield quinolinediones. Reaction with
chloroform gave dichloromethyl quinolinediones. Halogen exchange lead from the
chloro quinolinedionesto fluoro quinolinedones and to azido quinolinediones.
Similar the di loro quinolinedione react to the difluoro quinolinedione, which were
reduced to the 3-fluoro-4-hydroxyquinolone and react again with sulfuryl chloride to give
the mixed 3-chloro-3-fluoroquinolinedione.
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