Synthesis of 3-nitro- and 3-aminoquinoline-2,4-diones. An unexpected route to 3-hydroxyquinoline-2,4-diones |
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Authors: | Wolfgang Stadlbauer Herbert Lutschounig Gerda Schindler Theo Witoszynskyj Thomas Kappe |
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Abstract: | Nitration of 3-substituted-4-hydroxy-2(1H)-quinolones 1 with nitric acid leads either to 3-nitro- 2 or 3-hydroxyquinolinediones 3 , depending on the reaction conditions. 3-Substituted-3-hydroxyquinolinediones 3 are also obtained by oxidative hydroxylation with peracetic acid. Amination of 3-substituted-3-chloroquinolinediones 4 with ammonium hydroxide predominantly leads again to 3-substituted-3-hydroxyquinolinediones 3 , only in one case the 3-aminoquinolinedione 5 could be isolated. With morpholine or pyridine as amines the expected 3-aminoquinolinediones 6 and 7 were obtained. |
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