Premium
Synthesis of 3‐heptyl‐ and 3‐nonyl‐2,4(1 H ,3 H )‐quinolinediones
Author(s) -
Laschober Rita,
Stadlbauer Wolfgang
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001195
Subject(s) - chemistry , sodium azide , halogenation , potassium , medicinal chemistry , azide , potassium fluoride , sodium , fluoride , sodium fluoride , organic chemistry , stereochemistry , inorganic chemistry
3‐Alkl‐3‐hydroxy‐2,4‐(1 H ,3 H )‐quinolinediones 4 , which are metabolites of some Pseudomonas species, were synthesized by oxidation of the corresponding 4‐hydroxy‐2(1 H )‐quinolones 3 . By halogenation of 3 the 3‐chloro‐ and 3‐bromo‐2,4‐(1 H ,3 H )‐quinolinediones 5 and 7 , respectively, are obtained. Exchange of the chloro substitutent in 5 with sodium azide yields the 3‐azido derivatives 8 , while reaction with potassium fluoride affords the 3‐fluoroquinolinediones 6 .