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Thermal cyclization of 4‐azido‐3‐nitropyridines to furoxanes
Author(s) -
Stadlbauer Wolfgang,
Fiala Werner,
Fischer Michaela,
Hojas Gerhard
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370537
Subject(s) - chemistry , furoxan , sodium azide , thermal decomposition , nitration , azide , nitro , medicinal chemistry , decomposition , organic chemistry , nitric oxide , alkyl
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).