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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

✍ Scribed by Roschger, Peter ;Stadlbauer, Wolfgang

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 350 KB
Volume: 1991
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199119910174

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✦ Synopsis

Abstract

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).

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