CuI-Catalyzed Amination of Arylhalides with Guanidines or Amidines: A Facile Synthesis of 1-H-2-Substituted Benzimidazoles

被引：103

作者：

Deng, Xiaohu ^{[1
]}

McAllister, Heather ^{[1
]}

Mani, Neelakandha S. ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev, San Diego, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

N BOND FORMATION; EFFICIENT METHOD; CASCADE REACTIONS; VINYL HALIDES; ARYL HALIDES; ANTAGONISTS; IMIDAZOLES; POTENT; HYDROCHLORIDES; HETEROCYCLES;

D O I：

10.1021/jo900912h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CuI/L5 (N,N'-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-aminobenzimidazoles through tandem aminations of 1,2-dihaloarenes in modest yields. This methodology is also applicable for the preparation of I-H or 1-substutituted 2-aryl- or 2-alkyl-benzimidazoles.

引用

页码：5742 / 5745

页数：4

共 42 条

[1]

Alamgir M, 2007, TOP HETEROCYCL CHEM, V9, P87, DOI 10.1007/7081_2007_088

[2] Synthesis of pyrazino[1,2-a]benzimidazol-1(2H)ones via a microwave assisted Buchwald-Hartwig type reaction [J].

Alen, Jo ;

Robeyns, Koen ;

De Borggraeve, Wim M. ;

Van Meervelt, Luc ;

Compernolle, Frans .

TETRAHEDRON, 2008, 64 (35) :8128-8133

[3] Copper-catalyzed N-arylation of imidazoles and benzimidazoles [J].

Altman, Ryan A. ;

Koval, Erica D. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6190-6199

[4] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].

Anderson, Kevin W. ;

Tundel, Rachel E. ;

Ikawa, Takashi ;

Altman, Ryan A. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527

[5] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].

Bahrami, Kiumars ;

Khodaei, M. Mehdi ;

Naali, Fardin .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837

[6] ANTIINFLAMMATORY ACTIVITY OF SUBSTITUTED 6-HYDROXYPYRIMIDO[2,1-F]PURINE-2,4,8(1H,3H,9H)-TRIONES - ATYPICAL NONSTEROIDAL ANTIINFLAMMATORY AGENTS [J].

BLYTHIN, DJ ;

KAMINSKI, JJ ;

DOMALSKI, MS ;

SPITLER, J ;

SOLOMON, DM ;

CONN, DJ ;

WONG, SC ;

VERBIAR, LL ;

BOBER, LA ;

CHIU, PJS ;

WATNICK, AS ;

SIEGEL, MI ;

HILBERT, JM ;

MCPHAIL, AT .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :1099-1113

[7] Selection of a respiratory syncytial virus fusion inhibitor clinical candidate. 2. Discovery of a morpholinopropylaminobenzimidazole derivative (TMC353121) [J].

Bonfanti, Jean-Francois ;

Meyer, Christophe ;

Doublet, Frederic ;

Fortin, Jerome ;

Muller, Philippe ;

Queguiner, Laurence ;

Gevers, Tom ;

Janssens, Peggy ;

Szel, Heidi ;

Willebrords, Rudy ;

Timmerman, Philip ;

Wuyts, Koen ;

van Remoortere, Pieter ;

Janssens, Frans ;

Wigerinck, Piet ;

Andries, Koen .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (04) :875-896

[8] An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry [J].

Brain, CT ;

Steer, JT .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6814-6816

[9] An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles [J].

Brain, CT ;

Brunton, SA .

TETRAHEDRON LETTERS, 2002, 43 (10) :1893-1895

[10] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

← 1 2 3 4 5 →