4.6 Article

Metal-free regioselective C-3 nitration of quinoline N-oxides with tert-butyl nitrite

Journal

RSC ADVANCES
Volume 5, Issue 41, Pages 32835-32838

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra04632g

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Funding

  1. Chinese Academy of Sciences
  2. National Natural Science Foundation of China [21133011, 21373246]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDA09030104]

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A direct and eco-friendly nitration methodology to synthesize 3-nitroquinoline N-oxides from quinoline N-oxides using tert-butyl nitrite as both the nitro source and oxidant has been developed. Although this reaction undergoes a free radical process, it exhibits high regioselectivity and can be smoothly scaled up to gram scale.

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