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Synthesis of 3‐nitro‐ and 3‐aminoquinoline‐2,4‐diones. An unexpected route to 3‐hydroxyquinoline‐2,4‐diones
Author(s) -
Stadlbauer Wolfgang,
Lutschounig Herbert,
Schindler Gerda,
Witoszynskyj Theo,
Kappe Thomas
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290627
Subject(s) - chemistry , nitration , peracetic acid , morpholine , amination , ammonium hydroxide , medicinal chemistry , nitro , pyridine , nitric acid , ammonia , hydroxylation , formic acid , hydroxide , organic chemistry , hydrogen peroxide , alkyl , enzyme , catalysis
Abstract Nitration of 3‐substituted‐4‐hydroxy‐2(1 H )‐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.