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77. Thermal Cyclization of 4-Azido-3-nitropyridines to Furoxanes (Organic azides in heterocyclic synthesis, 26)
W. Stadlbauer, W. Fiala. M. Fischer, G. Hojas, J. Heterocycl. Chem., 37, 1253-1256 (2000).

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 furoxanes 6 and 12. Desoxygenation of the furoxan 6 with triphenylphosphane gave the furazane 7. Thermal decomposition conditions pf the azide 4 and the desoxygenation reaction of 6 to 7 were studied by differential scanning calorimetry (DSC).


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