Journal of Heterocyclic Chemistry p. 627 - 636 (1998)
Update date:2022-08-05
Topics:
Stadlbauer, Wolfgang
Prattes, Susanne
Fiala, Werner
4-Azido-2-oxoquinoline-3-carboxylates and 4-azidocoumarin-3-carboxylates 6, which were obtained from the corresponding 4-hydroxy derivatives 1 via 4-tosylates 2 or 4-chloro compounds 4, cyclized upon thermolysis to 3-alkoxyisoxazolo[4,3-c]quinolin-4(5H)-ones or the corresponding coumarins 8, whereas at slightly higher temperatures a 3-O, 4-O-rearrangement took place to give the 4-alkoxy-isoxazolo[4,3-c]-quinolin-3-ones and the corresponding coumarins 9. The necessary reaction conditions could be obtained easily with the help of differential scanning calorimetry.
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