An efficient and facile synthesis of benzimidazo [1,2-a]benzimidazoles via copper-catalyzed domino addition/double cyclization

被引:20
作者
Yuan, Guodong [1 ]
Liu, Haiquan [1 ]
Gao, Jilong [1 ]
Xu, Hongjuan [1 ]
Jiang, Liu [1 ]
Wang, Xiaoxia [1 ]
Lv, Xin [1 ]
机构
[1] Zhejiang Normal Univ, Coll Chem & Life Sci, Zhejiang Key Lab React Chem Solid Surfaces, Jinhua 321004, Peoples R China
基金
中国国家自然科学基金;
关键词
PHARMACOLOGICAL-ACTIVITY; DERIVATIVES; VERSATILE; AGENTS; DNA;
D O I
10.1039/c4ra01181c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed synthesis of benzimidazo[1,2-a]benzimidazoles by domino addition/double cyclization of bis-(o-haloaryl)carbodiimides with primary amines was developed. A variety of the desired polycyclic benzimidazoles were efficiently and facilely assembled. Multibonds and polycyclic moieties were directly constructed in one pot. 2-Bromo-2'-iodo-diarylcarbodiimides gave good selectivity.
引用
收藏
页码:21904 / 21908
页数:5
相关论文
共 39 条
[1]   SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 9-R-2-HALOGENOPHENYLIMIDAZO[1,2-a]BENZIMIDAZOLES [J].
Anisimova, V. A. ;
Spasov, A. A. ;
Tolpygin, I. E. ;
Minkin, V. I. ;
Chernikov, M. V. ;
Yakovlev, D. S. ;
Stukovina, A. Yu. ;
Goryagin, I. I. ;
Grechko, O. Yu. ;
Kirillova, N. V. ;
Kosolapov, V. A. ;
Tibir'kova, E. V. ;
Salaznikova, O. A. ;
Naumenko, L. V. ;
Gurova, N. A. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2010, 44 (07) :345-351
[2]   SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF SALTS OF 3-ACETYL-2-R-9-DIALKYLAMINOETHYLIMIDAZO[1,2-a]BENZIMIDAZOLES [J].
Anisimova, V. A. ;
Spasov, A. A. ;
Tolpygin, I. E. ;
Kosolapov, V. A. ;
Kucheryavenko, A. F. ;
Gurova, N. A. ;
Grechko, O. Yu. ;
Kirillova, N. V. ;
El'tsova, L. V. ;
Naumenko, L. V. ;
Sysueva, V. D. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2010, 44 (03) :117-122
[3]   SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 3-(2,2,2-TRICHLORO-1-HYDROXYETHYL)IMIDAZO [1,2-a]BENZIMIDAZOLE DIHYDROCHLORIDES [J].
Anisimova, V. A. ;
Spasov, A. A. ;
Kosolapov, V. A. ;
Tolpygin, I. E. ;
Porotikov, V. I. ;
Kucheryavenko, A. F. ;
Sysoeva, V. A. ;
Tibir'kova, E. V. ;
El'tsova, L. V. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2009, 43 (09) :491-494
[4]  
[Anonymous], DOMINO REACTIONS IN
[5]   Cascade Palladium- and Copper-Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors [J].
Ball, Catherine J. ;
Willis, Michael C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) :425-441
[6]   Medical implications of benzimidazole derivatives as drugs designed for targeting DNA and DNA associated processes [J].
Bhattacharya, Santanu ;
Chaudhuri, Padmaparna .
CURRENT MEDICINAL CHEMISTRY, 2008, 15 (18) :1762-1777
[7]   First synthesis of an aziridinyl fused pyrrolo[1,2-a]benzimidazole and toxicity evaluation towards normal and breast cancer cell lines [J].
Bonham, Sarah ;
O'Donovan, Liz ;
Carty, Michael P. ;
Aldabbagh, Fawaz .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) :6700-6706
[8]   Influence of Dielectric Surface Chemistry on the Microstructure and Carrier Mobility of an n-Type Organic Semiconductor [J].
Dhagat, Parul ;
Haverinen, Hanna M. ;
Kline, R. Joseph ;
Jung, Youngsuk ;
Fischer, Daniel A. ;
DeLongchamp, Dean M. ;
Jabbour, Ghassan E. .
ADVANCED FUNCTIONAL MATERIALS, 2009, 19 (15) :2365-2372
[9]   Design, synthesis and bioevaluation of dihydropyrazolo[3,4-b]pyridine and benzo[4,5]imidazo[1,2-a]pyrimidine compounds as dual KSP and Aurora-A kinase inhibitors for anti-cancer agents [J].
Fu, Rong-geng ;
You, Qi-dong ;
Yang, Lei ;
Wu, Wu-tong ;
Jiang, Cheng ;
Xu, Xiao-li .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (22) :8035-8043
[10]   Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives [J].
Hamdy, Nehal A. ;
Gamal-Eldeen, Amira M. ;
Abdel-Aziz, Hatem A. ;
Fakhr, Issa. M. I. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :463-470