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.