Chinese Journal of Applied Chemistry ›› 2011, Vol. 28 ›› Issue (04): 376-381.DOI: 10.3724/SP.J.1095.2011.00381
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ZHAO Xiaofeng, LIU Zuliang*
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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-osition 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.
Key words: amino-dinitropyridine, amino-dinitropyridine-oxide, VNS amination, amination reagent
CLC Number:
O626.3
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(04): 376-381.
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URL: http://yyhx.ciac.jl.cn/EN/10.3724/SP.J.1095.2011.00381
http://yyhx.ciac.jl.cn/EN/Y2011/V28/I04/376