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50. Synthesis of 3-nitro- and 3-aminoquinoline-2,4-diones. An unexpected route to 3-hydroxy-quinoline-2,4-diones
Stadlbauer W., Lutschounig H., Schindler G., Witoszynskyj T., Kappe T. J. Heterocycl. Chem. 29 (1992) 1535-40.

Abstract: Nitration of 3-substituted-4-hydroxy-2(1H)-quinolones with nitric acid leads either to 3-nitro- or 3-hydroxyquinolinediones, depending on the reaction conditions. 3-Substituted-3-hydroxyquinolinediones are also obtained by oxidative hydroxylation with peroxyacetic acid. Amination of 3-substituted-3-chloroquinolinediones) with ammonium hydroxide predominantly leads again to 3-substituted-3-hydroxyquinoline- diones, only in one case the 3-aminoquinolinedione could be isolated. With morpholine ore pyridine as amines the expected 3-aminoquinolinediones were obtained.


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