Copper-catalyzed synthesis of benzimidazoles via cascade reactions of o-haloacetanilide derivatives with amidine hydrochlorides

被引：159

作者：

Yang, Daoshan ^{[1
]}

Fu, Hua ^{[1
]}

Hu, Liming ^{[2
]}

Jiang, Yuyang ^{[1
,3
]}

Zhao, Yufen ^{[1
]}

机构：

[1] Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol Mini, Dept Chem, Beijing 100084, Peoples R China

[2] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

[3] Tsinghua Univ, Key Lab Chem Biol Guangdong Prov, Grad Sch Shenzhen, Shenzhen 518057, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 19期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/jo8014984

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient method for the synthesis of benzimidazoles via cascade reactions of o-haloacetoanilide derivatives with amidine hydrochlorides. The protocol uses 10 mol % CuBr as the catalyst, CS2CO3 as the base, and DMSO as the solvent, and no ligand is required. The procedure proceeds via the sequential coupling of o-haloacetoanilide derivatives with amidines, hydrolysis of the intermediates (amides), and intramolecular cyclization with the loss of NH3 to give 2-substituted 1H-benzimidazoles.

引用

页码：7841 / 7844

页数：4

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