Magnesiation of Pyridine N-Oxides via Iodine or Bromine-Magnesium Exchange: A Useful Tool for Functionalizing Pyridine N-Oxides

被引：43

作者：

Duan, Xin-Fang ^{[1
]}

Ma, Zi-Qian ^{[1
]}

Zhang, Fang ^{[1
]}

Zhang, Zhan-Bin ^{[1
]}

机构：

[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 02期

关键词：

HALOGEN-LITHIUM EXCHANGE; ONE-STEP CONVERSION; DIRECT ARYLATION; REGIOSELECTIVE METALATION; ASYMMETRIC ALLYLATION; EFFICIENT REAGENTS; GRIGNARD-REAGENTS; DERIVATIVES; ALKYLATION; CHLORIDES;

D O I：

10.1021/jo802172f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodo- or 2-bromopyridine N-oxides were readily magnesiated with i-PrMgCl center dot LiCl via the iodine or bromine-magnesium exchange. The bromine adjacent to pyridine N-oxide (at the 2- or 6-position) can be regioselectively magnesiated in the presence of other position substituted halogens. This method was tested in various substituted pyridine N-oxide systems, and has been successfully applied to the total synthesis of caerulomycins E and A.

引用

页码：939 / 942

页数：4

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