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Citation: ZHAO Xiaofeng, LIU Zuliang. Amination of Aminonitropyridine and Its N-Oxide via Vicarious Nucleophilic Substitution of Hydrogen[J]. Chinese Journal of Applied Chemistry, ;2011, 28(4): 376-381. doi: 10.3724/SP.J.1095.2011.00381 shu

Amination of Aminonitropyridine and Its N-Oxide via Vicarious Nucleophilic Substitution of Hydrogen

ZHAO Xiaofeng ,
LIU Zuliang ^,

1.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: LIU Zuliang,
Received Date: 29 June 2010
Available Online: 28 September 2010

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.
- amino-dinitropyridine,
- amino-dinitropyridine-oxide,
- VNS amination,
- amination reagent
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