Lithiation of 1-arylimidazol-2(1H)-ones and 1-aryl-4,5-dihydroimidazol-2(1H)-ones

被引：12

作者：

Llopart, CC ^{[1
]}

Ferrer, C ^{[1
]}

Joule, JA ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2004年 / 82卷 / 11期

关键词：

ortho-lithation; ureas for directed ortho metalation; 1-arylimidazol-2-ones; 1-arylimidazolidin-2-ones;

D O I：

10.1139/V04-137

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.

引用

页码：1649 / 1661

页数：13

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