One-Pot, Two-Step Synthesis of Imidazo[1,2-a]benzimidazoles via A Multicomponent [4+1] Cycloaddition Reaction

被引：23

作者：

Hsiao, Ya-Shan ^{[1
]}

Narhe, Bharat D. ^{[1
]}

Chang, Ying-Sheng ^{[1
]}

Sun, Chung-Ming ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan

来源：

ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 10期

关键词：

microwave irradiation; 4+1] cycloaddition; imidazo[1,2-a]benzimidazoles; three-component reaction; DESIGN;

D O I：

10.1021/co400075z

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A one-pot, two-step synthesis of imidazo[1,2-a]benzimidazoles has been achieved by a three-component reaction of 2-aminobenzimidazoles with an aromatic aldehyde and an isocyanide. The reaction involving condensation of 2-aminobenzimidazole with an aldehyde is run under microwave activation to generate an imine intermediate under basic conditions which then undergoes [4 + 1] cycloaddition with an isocyanide.

引用

页码：551 / 555

页数：5

共 26 条

[1] Antitumor activity of new substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and study of their effect on the cell cycle [J].

Andreani, A ;

Granaiola, M ;

Leoni, A ;

Locatelli, A ;

Morigi, R ;

Rambaldi, M ;

Garaliene, V ;

Welsh, W ;

Arora, S ;

Farruggia, G ;

Masotti, L .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (17) :5604-5607

[2]

[Anonymous], MICROWAVES ORGANIC S

[3] N-Fused Imidazoles As Novel Anticancer Agents That Inhibit Catalytic Activity of Topoisomerase IIα and Induce Apoptosis in G1/S Phase [J].

Baviskar, Ashish T. ;

Madaan, Chetna ;

Preet, Ranjan ;

Mohapatra, Purusottam ;

Jain, Vaibhav ;

Agarwal, Amit ;

Guchhait, Sankar K. ;

Kundu, Chanakya N. ;

Banerjee, Uttam C. ;

Bharatam, Prasad V. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (14) :5013-5030

[4]

Bohm Hans-Joachim, 2004, Drug Discov Today Technol, V1, P217, DOI 10.1016/j.ddtec.2004.10.009

[5] 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

[6] Base-Catalyzed Povarov Reaction: An Unusual [1,3] Sigmatropic Rearrangement to Dihydropyrimidobenzimidazoles [J].

Chen, Chih-Hau ;

Yellol, Gorakh S. ;

Lin, Po-Tsung ;

Sun, Chung-Ming .

ORGANIC LETTERS, 2011, 13 (19) :5120-5123

[7] Microwave Promoted Simple, Efficient and Regioselective Synthesis of Trisubstituted Imidazo[1,2-a]benzimidazoles on Soluble Support [J].

Chen, Li-Hsun ;

Hsiao, Ya-Shan ;

Yellol, Gorakh S. ;

Sun, Chung-Ming .

ACS COMBINATORIAL SCIENCE, 2011, 13 (02) :112-119

[8] A Telescoped Route to 2,6-Disubstituted 2,3,4,5-Tetrahydropyridines and 2,6-syn-Disubstituted Piperidines: Total Synthesis of (-)-Grandisine G [J].

Cuthbertson, James D. ;

Taylor, Richard J. K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1490-1493

[9] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[10] Chemistry and Biology Of Multicomponent Reactions [J].

Domling, Alexander ;

Wang, Wei ;

Wang, Kan .

CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135

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