Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives

被引：31
作者：
Gan, Zongjie [1 ,2 ]
Tian, Qingqiang [1 ,2 ]
Shang, Suqin [1 ,2 ]
Luo, Wen [1 ,2 ]
Dai, Zeshu [1 ,2 ]
Wang, Huajun [1 ,2 ]
Li, Dan [1 ,2 ]
Wang, Xuetong [1 ,2 ]
Yuan, Jianyong [1 ,2 ]
机构：
[1] Chongqing Med Univ, Dept Med Chem, Coll Pharm, Chongqing 400016, Peoples R China
[2] Chongqing Med Univ, Chongqing Res Ctr Pharmaceut Engn, Chongqing 400016, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 52期
关键词：
Imidazolium chloride; Benzimidazoles; 2-Substituted benzimidazoles; Synthesis; CONVENIENT SYNTHESIS; BENZOTHIAZOLES; HETEROCYCLES; CYCLIZATION; SOLVENT; AMINES; ACIDS; CO2;
D O I：
10.1016/j.tet.2018.11.014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7450 / 7456
页数：7
相关论文
共 34 条
[1]  
[Anonymous], SCREEN
[2]   An ammonium molybdate deposited amorphous silica coated iron oxide magnetic core-shell nanocomposite for the efficient synthesis of 2-benzimidazoles using hydrogen peroxide [J].
Bai, Guoyi ;
Lan, Xingwang ;
Liu, Xiaofang ;
Liu, Chen ;
Shi, Lingjuan ;
Chen, Qingzhi ;
Chen, Guofeng .
GREEN CHEMISTRY, 2014, 16 (06) :3160-3168
[3]   Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)3 catalyst in the reaction selectivity [J].
Cano, Natividad Herrera ;
Uranga, Jorge G. ;
Nardi, Monica ;
Procopio, Antonio ;
Wunderlin, Daniel A. ;
Santiago, Ana N. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 :2410-2419
[4]   Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives [J].
Chen, Gaozhi ;
Liu, Zhiguo ;
Zhang, Yali ;
Shan, Xiaoou ;
Jiang, Lili ;
Zhao, Yunjie ;
He, Wenfei ;
Feng, Zhiguo ;
Yang, Shulin ;
Liang, Guang .
ACS MEDICINAL CHEMISTRY LETTERS, 2013, 4 (01) :69-74
[5]   Nano rod-shaped and reusable basic Al2O3 catalyst for N-formylation of amines under solvent-free conditions: A novel, practical and convenient 'NOSE' approach [J].
Das, Vijay Kumar ;
Devi, Rashmi Rekha ;
Raul, Prasanta Kumar ;
Thakur, Ashim Jyoti .
GREEN CHEMISTRY, 2012, 14 (03) :847-854
[6]   Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing -CONH- bridge with benzimidazole:: Screening in vitro antimicrobial activity with various microorganisms [J].
Desai, Krunal G. ;
Desai, Kishor R. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8271-8279
[7]   SYNTHESIS OF A CONFORMATIONALLY CONSTRAINED ANALOG OF BW A78U, AN ANTICONVULSANT ADENINE DERIVATIVE [J].
DESAUBRY, L ;
WERMUTH, CG ;
BOURGUIGNON, JJ .
TETRAHEDRON LETTERS, 1995, 36 (24) :4249-4252
[8]   Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives [J].
EL-Sayed, Taghreed H. ;
Aboelnaga, Asmaa ;
Hagar, Mohamed .
MOLECULES, 2016, 21 (09)
[9]   Ammonium Chloride-catalyzed Synthesis of Benzo-fused Heterocycles from o-Substituted Anilines and Orthoesters [J].
Fortenberry, Chelsea ;
Nammalwar, Baskar ;
Bunce, Richard A. .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2013, 45 (01) :57-65
[10]   Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst [J].
Gao, Xiang ;
Yu, Bo ;
Mei, Qingqing ;
Yang, Zhenzhen ;
Zhao, Yanfei ;
Zhang, Hongye ;
Hao, Leiduan ;
Liu, Zhimin .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (10) :8282-8287
1234