Mild and Regioselective N-Alkylation of 2-Pyridones in Water

被引：51

作者：

Hao, Xin ^{[1
]}

Xu, Zhongmiao ^{[1
]}

Lu, Hongfu ^{[1
]}

Dai, Xuedong ^{[1
]}

Yang, Ting ^{[1
]}

Lin, Xichen ^{[1
]}

Ren, Feng ^{[1
]}

机构：

[1] GlaxoSmithKline, Res & Dev, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 14期

关键词：

HETEROCYCLIC AMBIDENT ANIONS; O-ALKYLATION; ROOM-TEMPERATURE; PYRIDONES; N-ALKYL-2(1H)-PYRIDONES; 2-ALKOXYPYRIDINES; IODOBENZENES; CHEMISTRY; ARYLATION; CATALYSIS;

D O I：

10.1021/acs.orglett.5b01628

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and regioselective N-alkylation reaction of 2-pyridones in water has been developed. Tween 20 (2% w/w) was added to create a micellar system for improved solubility of starting materials, which leads to enhanced reaction rates. The protocol demonstrated a wide substrate scope with good isolated yield's (40-94%) for all of the 24 examples evaluated. High regioselectivity favoring N-alkylation over O-alkylation was observed for benzyl halides (>5:1), primary alkyl halides (>6:1), and bulky and less reactive secondary alkyl halides (>2.4:1).

引用

页码：3382 / 3385

页数：4

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