1,2‐Addition of Alkyl Grignard Reagents to the Nitro Group: Simple Access to 2‐[Alkyl(hydroxy)amino]pyridine N‐Oxides and 2‐Alkylaminopyridine N‐Oxides
1,2‐Addition of Alkyl Grignard Reagents to the Nitro Group: Simple Access to 2‐[Alkyl(hydroxy)amino]pyridine N‐Oxides and 2‐Alkylaminopyridine N‐Oxides
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DOI：
10.1002/ejoc.201300801
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发表时间：
2013-09
影响因子：
2.8
通讯作者：
Kun Liu;Fang Zhang;Xinfang Duan
中科院分区：
文献类型：
--
作者：
Kun Liu;Fang Zhang;Xinfang Duan
The unexpected 1,2-addition of various alkyl Grignard reagents to nitro groups is described. A simple treatment of a 2-nitropyridine N-oxide with an alkyl Grignard reagent results in a 2-[alkyl(hydroxy)amino]pyridine N-oxide as the result of a 1,2-addition to the nitro group. Moreover, 2-(alkylamino)pyridine N-oxides can also be obtained from this 1,2-addition after a reductive workup by using NaBH4/FeCl3. This work shows another facet of the reactions between alkyl Grignard reagents and nitro groups, and provides a simple method for the formation of carbon–nitrogen bonds without a transition metal catalyst.
