title: Arylation, alkenylation, and alkylation of 2-halopyridine N-oxides with grignard reagents: a solution to the problem of C2/C6 regioselective functionalization of pyridine derivatives.
abstract: A facile arylation, alkenylation, and alkylation of functionalized 2-halopyridine N-oxides with various Grignard reagents was developed. It represented a highly efficient and selective C-H bond functionalization of pyridine derivatives in the presence of reactive C-Cl or C-Br bonds. Using Cl or Br as a blocking group, C2/C6 site-controllable functionalization of pyridine derivatives has been achieved. Various pyridine compounds can be prepared as illustrated in the total syntheses of Onychine, dielsine, and PARP-1 inhibitor GPI 16539.
authors: College of Chemistry, Beijing Normal University, Beijing 100875, China.
authors: Song
authors: S
authors: Zhang
authors: Lian-Yan
authors: LY
authors: Liao
authors: Fang
authors: F
authors: Zhang
authors: Xin-Fang
authors: XF
authors: Duan
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D044950:Flavanones / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D010879:Piperazines; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C476143:2-(4-methylpiperazin-1-yl)-5H-benzo(c)(1,5)naphthyridin-6-one; D000475:Alkenes; D003497:Cyclic N-Oxides; D044950:Flavanones; D007202:Indicators and Reagents; D009287:Naphthyridines; D010879:Piperazines; D010880:Piperidines; D011725:Pyridines; D011728:Pyridones; C054955:onychine