Abstract
2-Amino-3,5-dinitropyridine(1) and 2-amino-3,5-dinitropyridine-1-oxide(3) have been aminated by various nucleophilic substitution reaction,using hydroxylamine hydrochloride,4-amino-1,2,4-triazole and 1,1,1-trimethylhydrazinium iodide as aminating agents.Based on amination via vicarious nucleophilic substitution(VNS) of hydrogen,the stereo-electronic effects of aminating agents and reactants on the composition and yield of target compounds were discussed.Reactants 1 and 3 were aminated at the 6-position and 4-position using hydroxylamine with a yield in the range of 64%~89%.Reactions of 1 and 3 respectively with 4-amino-1,2,4-triazole or 1,1,1-trimethylhydrazinium generated compounds which were aminated at the 6-position,with a yield over 90%.Under the same conditions,the yields for the target compounds were improved with the increase of the activities of aminating agents.
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