Organic azides in heterocyclic synthesis, part 26 - Thermal cyclization of4-azido-3-nitropyridines to furoxanes

Authors
Stadlbauer, W Fiala, W Fischer, M Hojas, G
Citation
W. Stadlbauer et al., Organic azides in heterocyclic synthesis, part 26 - Thermal cyclization of4-azido-3-nitropyridines to furoxanes, J HETERO CH, 37(5), 2000, pp. 1253-1256
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
5
Year of publication
2000
Pages
1253 - 1256
Database
ISI
SICI code
0022-152X(200009/10)37:5<1253:OAIHSP>2.0.ZU;2-M
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 r eaction of 6 to 7 were studied by differential scanning calorimetry (DSC).