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Organic azides in heterocyclic synthesis, 12. Thermal cyclization of 4‐azido‐3‐formyl‐2‐quinolones to isoxazolo[4,3‐ c ]quinolones
Author(s) -
Roschger Peter,
Stadlbauer Wolfgang
Publication year - 1991
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.199119910174
Subject(s) - quinolone , chemistry , azide , thermal decomposition , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , antibiotics , biochemistry
Thermolysis of the 4‐azido‐3‐formyl‐2‐quinolone 6 , which was prepared from the 4‐hydroxy‐2‐quinolone 1 , afforded the ringclosed isoxazoloquinolone 7 . 3‐(Arylaminomethylene)‐2,4‐quinolinediones 2 could not be transformed into an azide precursor in order to obtain the corresponding pyrazoloquinolone but yielded by attempted chlorination either 5‐methyldibenzo[ b,h ][1,6]naphthyridine‐6(5 H )‐one ( 9 ) or 4‐chloro‐3‐formyl‐1‐methyl‐2(1 H )‐quinolone ( 5 ).