Novel Strategy for Synthesis of Substituted Benzimidazo[1,2-a]quinolines

被引:53
作者
Kato, Jun-ya [1 ]
Ito, Yutaro [1 ]
Ijuin, Ryosuke [1 ]
Aoyama, Hiroshi [1 ]
Yokomatsu, Tsutomu [1 ]
机构
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
关键词
EFFICIENT ROUTE; N-ARYLATION; DNA-BINDING; DERIVATIVES; AMINATION; PART;
D O I
10.1021/ol4017723
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of benzimidazo[1,2-a]quinolines under transition-metal-free conditions has been developed through a cascade reaction involving sequential aromatic nucleophilic substitution and intramolecular Knoevenagel condensation reactions. This method is applicable for the synthesis of a wide range of benzimidazo[1,2-a]quinoline derivatives from readily available 2-fluoroarylaldehyde and benzimidazole substrates.
引用
收藏
页码:3794 / 3797
页数:4
相关论文
共 18 条
[1]   The therapeutic journey of benzimidazoles: A review [J].
Bansal, Yogita ;
Silakari, Om .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (21) :6208-6236
[2]   NEW BENZIMIDAZOLE SYNTHESIS [J].
BENINCORI, T ;
SANNICOLO, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) :1029-1033
[3]   Synthesis of Aza-Fused Polycyclic Quinolines through Copper-Catalyzed Cascade Reactions [J].
Cai, Qian ;
Li, Zhengqiu ;
Wei, Jiajia ;
Fu, Liangbin ;
Ha, Chengyong ;
Pei, Duanqing ;
Ding, Ke .
ORGANIC LETTERS, 2010, 12 (07) :1500-1503
[4]   Catalyst-Free N-Arylation Using Unactivated Fluorobenzenes [J].
Diness, Frederik ;
Fairlie, David P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) :8012-8016
[5]   Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines.: Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3 [J].
Hranjec, Marijana ;
Kralj, Marijeta ;
Piantanida, Ivo ;
Sedic, Mirela ;
Suman, Lidija ;
Pavelic, Kresimir ;
Karminski-Zamola, Grace .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (23) :5696-5711
[6]   Synthesis of novel benzimidazolyl-substituted acrylonitriles and amidino-substituted enzimidazo[1,2-a]quinolines [J].
Hranjec, Marijana ;
Karminski-Zamola, Grace .
MOLECULES, 2007, 12 (08) :1817-1828
[7]   Novel imidazo[4,5-b]pyridine and triaza-benzo[c]fluorene derivatives: Synthesis, antiproliferative activity and DNA binding studies [J].
Hranjec, Marijana ;
Lucic, Borka ;
Ratkaj, Ivana ;
Pavelic, Sandra Kraljevic ;
Piantanida, Ivo ;
Pavelic, Kresimir ;
Karminski-Zamola, Grace .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) :2748-2758
[8]   Development of a new cascade reaction for convergent synthesis of pyrazolo[1,5-a]quinoline derivatives under transition-metal-free conditions [J].
Kato, Jun-ya ;
Aoyama, Hiroshi ;
Yokomatsu, Tsutomu .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (07) :1171-1178
[9]  
Khilya O V., 2004, Chem. Heterocycl. Compd, V40, P1063, DOI [10.1023/B:COHC.0000046698.75658.49, DOI 10.1023/B:COHC.0000046698.75658.49]
[10]   Orthogonal and auto-tandem catalysis:: Synthesis of dipyrido[1,2-a:2′,3′-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation [J].
Loones, KTJ ;
Maes, BUW ;
Meyers, C ;
Deruytter, J .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :260-264