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Thermal cyclization of 4-azido-3-nitropyridines to furoxanes

✍ Scribed by Wolfgang Stadlbauer; Werner Fiala; Michaela Fischer; Gerhard Hojas

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
326 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

4‐Chloro‐3‐nitro‐2‐pyridines 3 and 10, obtained from 4‐hydroxy‐2‐pyridones 1 and 8 after nitration and chlorination, gave with sodium azide 4‐azido‐3‐nitropyridines 4 and 11, which cyclized on thermolysis to furoxans 6 and 12. Desoxygenation of the furoxan 6 with triphenylphosphane gave the furazan 7. Thermal decomposition conditions of the azide 4 and the desoxygenation reaction of 6 to 7 were studied by differ ential scanning calorimetry (DSC).

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