AMINONITROPYRIDINES AND THEIR N-OXIDES

2,6-Diamino-3,5-dinitropyridine 1-oxide has been prepared by mixed aci d nitration of 2,6-diaminopyridine, followed by oxidation using hydrog en peroxide in acetic acid. 3,5-Dinitro-2,4,6-triaminopyridine has bee n prepared by oxidative amination of 2-chloro-3,5-dinitropyridine or 2 ,6-diamino-3,5-dinitropyridine using potassium permanganate in liquid ammonia, or by ''vicarious nucleophilic amination'' of 2,6-diamino-3,5 -dinitropyridine using hydroxylamine in aqueous potassium hydroxide. 3 ,5-Dinitro-2,4,6-triaminopyridine 1-oxide has been prepared by oxidati on of 3,5-dinitro-2,4,6-triaminopyridine using hydrogen peroxide in ac etic acid, and by ''vicarious nucleophilic amination'' of 2,6-diamino- 3,5-dinitropyridine 1-oxide. Nmr spectroscopy and single crystal X-ray diffraction studies have shown that these compounds have the planar s tructures and intra- and inter-molecular hydrogen bonding necessary to confer on the materials the high density, the thermal and chemical st ability, and the explosive insensitivity required for new insensitive energetic materials.