Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission

被引：98

作者：

Zhao, Dongbing

Hu, Junyi

Wu, Ningjie

Huang, Xiaolei

Qin, Xurong

Lan, Jingbo

You, Jingsong ^{[1
]}

机构：

[1] Sichuan Univ, W China Med Sch, Coll Chem, Key Lab Green Chem & Technol,Minist Educ, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 24期

关键词：

COPPER-CATALYZED SYNTHESIS; LIGHT-EMITTING-DIODES; BENZIMIDAZOLES; DERIVATIVES; AMINATION; DISCOVERY;

D O I：

10.1021/ol202807d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed two or fourfold amination was established that allows regiospecific synthesis of a diversity-oriented library of 1,2-disubstituted (hetero)aryl fused imidazoles, and provides an exceptional tool for the discovery of fluorescent scaffolds with tunable fluorescence emission. These fluorophores have been applied as fluorescent probes for live cell imaging.

引用

页码：6516 / 6519

页数：4

共 35 条

[1]

BAE JS, 2007, Patent No. 2007011170

[2] The high-pressure SNAr reaction of N-p-fluorobenzyl-2-chlorobenzimidazole with amines;: an approach to norastemizole and analogues [J].

Barrett, IC ;

Kerr, MA .

TETRAHEDRON LETTERS, 1999, 40 (13) :2439-2442

[3] Rapid microwave-assisted liquid-phase combinatorial synthesis of 2-(arylamino)benzimidazoles [J].

Bendale, PM ;

Sun, CM .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (04) :359-361

[4] Modular fluorescent benzobis(imidazolium) salts: Syntheses, photophysical analyses, and applications [J].

Boydston, Andrew J. ;

Vu, Peter D. ;

Dykhno, Olga L. ;

Chang, Vicki ;

Wyatt, Alvin R., II ;

Stockett, Adam S. ;

Ritschdbrff, Eric T. ;

Shear, Jason B. ;

Bielawski, Christopher W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (10) :3143-3156

[5] Phase-tunable fluorophores based upon benzobis(imidazolium) salts [J].

Boydston, Andrew J. ;

Pecinovsky, Cory S. ;

Chao, Steven T. ;

Bielawski, Christopher W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14550-+

[6] 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

[7] 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

[8] Combinatorial Discovery of Fluorescent Pharmacophores by Multicomponent Reactions in Droplet Arrays [J].

Burchak, Olga N. ;

Mugherli, Laurent ;

Ostuni, Mariano ;

Lacapere, Jean Jacques ;

Balakirev, Maxim Y. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) :10058-10061

[9] Developments Towards Regioselective Synthesis of 1,2-Disubstituted Benzimidazoles [J].

Carvalho, Luisa C. R. ;

Fernandes, Eduarda ;

Marques, M. Manuel B. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12544-12555

[10] Evolution of red organic light-emitting diodes: Materials and devices [J].

Chen, CT .

CHEMISTRY OF MATERIALS, 2004, 16 (23) :4389-4400

← 1 2 3 4 →