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

共 59 条

[1] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[2] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].

Antilla, JC ;

Baskin, JM ;

Barder, TE ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587

[3] Recent developments on proton conducting poly(2,5-benzimidazole) (ABPBI) membranes for high temperature polymer electrolyte membrane fuel cells [J].

Asensio, JA ;

Gómez-Romero, P .

FUEL CELLS, 2005, 5 (03) :336-343

[4] Design, synthesis, SAR, and biological evaluation of highly potent benzimidazole-spaced phosphono-α-amino acid competitive NMDA antagonists of the AP-6 type [J].

Baudy, RB ;

Fletcher, H ;

Yardley, JP ;

Zaleska, MM ;

Bramlett, DR ;

Tasse, RP ;

Kowal, DM ;

Katz, AH ;

Moyer, JA ;

Abou-Gharbia, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (10) :1516-1529

[5] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[6] Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction [J].

Bonnaterre, Florence ;

Bois-Choussy, Michele ;

Zhu, Jieping .

ORGANIC LETTERS, 2006, 8 (19) :4351-4354

[7] Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects [J].

Cai, Q ;

Zou, BL ;

Ma, DW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1276-1279

[8] 1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols [J].

Chen, Yao-Jung ;

Chen, Hsin-Hung .

ORGANIC LETTERS, 2006, 8 (24) :5609-5612

[9] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[10] Mild conditions for copper-catalysed N-arylation of pyrazoles [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709

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