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- Title
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.
- Authors
Liu, Kun‐Ming; Zhang, Fang; Duan, Xin‐Fang
- Abstract
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.
- Subjects
CHEMICAL reagents; GROUP 15 elements; TRANSITION metals; PYRIDINE; OXIDES
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 27, p6152
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300801