Synthesis of 2-substituted 1-hydroxyimidazoles through directed lithiation

被引：41

作者：

Eriksen, BL ^{[1
]}

Vedso, P ^{[1
]}

Morel, S ^{[1
]}

Begtrup, M ^{[1
]}

机构：

[1] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 01期

关键词：

D O I：

10.1021/jo970355+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon; halogen, silicon, or sulfur substituents at the 2-position, Subsequent debenzylation afforded 2-substituted 1-hydroxaimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

引用

页码：12 / 16

页数：5

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