Substitution of the nitro group with Grignard reagents: facile arylation and alkenylation of pyridine N-oxides.
The unprecedented substitution of a nitro group with aryl or alkenyl groups of Grignard reagents affords 2-aryl or alkenylpyridine N-oxides in modest to high yields with high chemoselectivity. This protocol allows a simple and clean synthesis of various 2-substituted pyridine N-oxides and the corresponding pyridine derivatives. Furthermore, straightforward one-pot iterative functionality of pyridine N-oxides could also be achieved simply by successive applications of two Grignard reagents.
College of Chemistry, Beijing Normal University, Beijing 100875, China.
Fang
F
Zhang
Song
S
Zhang
Xin-Fang
XF
Duan
D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
D003497:Cyclic N-Oxides; D007202:Indicators and Reagents; D009574:Nitro Compounds; D011725:Pyridines; C013229:pyridine N-oxide