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67. Ring Closure and Rearrangement Reactions of 4-Azido-2-oxo-quinoline- and 4-Azidocoumarin-3-carboxylates (Organic azides in heterocyclic synthesis, 23)
Stadlbauer W., Prattes S., Fiala W., J. Heterocyclic Chem., 35 (1998), 627-636

Abstract: The thermolytical decomposition of azides with an ester group in the ortho position gives two exothermic reaction steps . It was proved by synthesis that the first thermolytical reaction step gave, as ring closure product, the isoxazoles with the alkoxy group in the isoxazole ring, whereas at slightly higher temperatures a rearrangement to isoxazolones with the alkoxy group in the quinoline, coumarin or pyridine ring took place.


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