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Ring closure and rearrangement reactions of 4-azido-2-oxoquinoline-3-carboxylates and 4-azidocoumarin-3-carboxylates

✍ Scribed by Wolfgang Stadlbauer; Susanne Prattes; Werner Fiala

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
707 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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(5__H__)‐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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