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Web End = Mol Divers (2016) 20:575580 DOI 10.1007/s11030-015-9646-7
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Web End = Facile microwave-assisted synthesis of benzimidazole scaffolds via Ugi-type three-component condensation (3CC) reactions
Gui-Ting Song1,2,3 Zhi-Gang Xu1 Dian-Yong Tang1 Shi-Qiang Li1
Zhi-Gang Xie1 Hong-Liang Zhong1 Zhi-Wei Yang1
Jin Zhu2 Jin Zhang1 Zhong-Zhu Chen1
Received: 16 July 2015 / Accepted: 24 October 2015 / Published online: 18 November 2015 Springer International Publishing Switzerland 2015
Abstract Two series of fused benzimidazoles were synthesized via a facile, one-pot procedure under microwave irradiation. This procedure generated the desired products in high yields and could provide a useful synthetic platform with potential applications in medicinal chemistry.
Keywords Multicomponent reactions (MCRs)
Benzimidazole Three-component condensation (3-CC)
GroebkeBlackburn reaction Microwave irradiation
Cyclization
Introduction
Multicomponent reactions (MCRs), which include three or more reactants reacting simultaneously to form part of a new chemical entity, provide quicker and more efcient ways to synthesize nitrogen-containing heterocyclic com-
Electronic supplementary material The online version of this article (doi:http://dx.doi.org/10.1007/s11030-015-9646-7
Web End =10.1007/s11030-015-9646-7 ) contains supplementary material, which is available to authorized users.
B Jin Zhang
B Zhong-Zhu Chen
1 International Academy of Targeted Therapeutics andInnovation, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing 402160, China
2 Key Laboratory for Asymmetric Synthesis and Chiral Technology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
3 University of Chinese Academy of Sciences, Beijing 100049, China
pounds and have great potential for pharmaceutical industrial applications [1,2]. Fused heterocyclic compounds, such as imidazo[1,2-a]pyridines and 1H-benzo[d]imidazole, possess a wide range of interesting biological properties, including antibacterial [3], anticancer [4], antiparasitic [5], antibiotic [6,7], cytotoxic [810], antitumor [11], hypnotic [12], and anti-inammatory [3,13] activities. A variety of synthetic protocols have been developed for the preparation of imidazo[1,2-a]pyridine derivatives based on palladium- and copper-catalyzed cascade reactions involving CN and CC cross-coupling processes [1417]. An Ugi-type multicomponent reaction (MCR) (also referred to as GroebkeBlackburn or GroebkeBlackburnBienaym reaction) was recently reported for the preparation of 1H-benzo[d]imidazole derivatives [1821]. Numerous MCRs have been reported during the last decade for the...