Assembly of Substituted 1H-Benzimidazoles and 1,3-Dihydrobenzimidazol-2-ones via CuI/L-Proline Catalyzed Coupling of Aqueous Ammonia with 2-Iodoacetanilides and 2-Iodophenylcarbamates

被引：114

作者：

Diao, Xiaoqiong ^{[2
]}

Wang, Yuji ^{[2
]}

Jiang, Yongwen ^{[1
]}

Ma, Dawei ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 20期

基金：

中国国家自然科学基金;

关键词：

N-ARYLATION; ARYL HALIDES; AMINO-ACID; C-N; NITROGEN-HETEROCYCLES; TOPOISOMERASE-I; EFFICIENT; BENZIMIDAZOLES; LIGANDS; PHARMACOPHORE;

D O I：

10.1021/jo9017183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates affords the aryl amination products at room temperature, which undergo in situ additive cyclization under acidic conditions or heating to give substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones, respectively. A wide range of functional groups including ketone, nitro, iodo, bromo, and ester are tolerated under these reaction conditions, providing these heterocycles with great diversity.

引用

页码：7974 / 7977

页数：4

共 41 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] Evaluation of the Dmt-Tic pharmacophore:: Conversion of a potent δ-opioid receptor antagonist into a potent δ agonist and ligands with mixed properties [J].

Balboni, G ;

Guerrini, R ;

Salvadori, S ;

Bianchi, C ;

Rizzi, D ;

Bryant, SD ;

Lazarus, LH .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :713-720

[3] Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic [J].

Balboni, Gianfranco ;

Fiorini, Stella ;

Baldisserotto, Anna ;

Trapella, Claudio ;

Sasaki, Yusuke ;

Ambo, Akihiro ;

Marczak, Ewa D. ;

Lazarus, Lawrence H. ;

Salvadori, Severo .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :5109-5117

[4] Synthesis of Benzazoles by Hydrogen-Transfer Catalysis [J].

Blacker, A. John ;

Farah, Mohamed M. ;

Hall, Michael I. ;

Marsden, Stephen P. ;

Saidi, Ourida ;

Williams, Jonathan M. J. .

ORGANIC LETTERS, 2009, 11 (09) :2039-2042

[5] Conversion of sterically hindered diacylated 1,2-phenylenediamines into 2-substituted benzimidazoles [J].

Charton, J ;

Girault-Mizzi, S ;

Sergheraert, C .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (05) :492-497

[6] Synthesis of structurally diverse benzimidazolyl benzimidazolones by application of soluble polymer support [J].

Chen, Hsia-Yuan ;

Kulkarni, Manohar V. ;

Chen, Chih-Hau ;

Sun, Chung-Ming .

TETRAHEDRON, 2008, 64 (27) :6387-6394

[7] A concept of supported amino acid ionic liquids and their application in metal scavenging and heterogeneous catalysis [J].

Chen, Wen ;

Zhang, Yuanyuan ;

Zhu, Liangbo ;

Lan, Jingbo ;

Xie, Rugang ;

You, Jingsong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13879-13886

[8] 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

[9] A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant [J].

Du, Li-Hua ;

Wang, Yan-Guang .

SYNTHESIS-STUTTGART, 2007, (05) :675-678

[10] Prototropic tautomerism of heterocycles: Heteroaromatic tautomerism - General overview and methodology [J].

Elguero, J ;

Katritzky, AR ;

Denisko, OV .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 76, 2000, 76 :1-84

← 1 2 3 4 5 →