Transition-metal-free insertion of benzyl bromides into 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde: One-pot switchable syntheses of benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base |
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| Authors: | Huayan Xu Liang Xu Xiaowei Luo Junfeng Wang Xuefeng Zhou Bin Yang Ding Li Zaigang Luo Yonghong Liu Shengrong Liao |
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| Affiliation: | 1. College of Chemical Engineering, Anhui University of Science and Technology, Huainan, 232001, PR China;2. CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Research Center for Marine Microbes, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, PR China;3. School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, PR China |
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| Abstract: | A transition-metal-free insertion of benzyl group between aldehyde and imidazole of 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde was achieved for the first time. Two diverse sets of quinolin-4-one derivatives: benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones (2) and 3-arylquinolin-4-ones (3) were synthesized based on identical starting materials 2-(1H-benzo[d]imidazol-1-yl)benzaldehydes (1) and benzyl bromides. In the preparations, two key intermediates I and II were involved and might be synthesized in situ through the reaction of an intra-Breslow intermediate with benzyl bromide via an enol attack in the presence of base or a NHC-based enamine attack in the absence of base, respectively, in which the intra-Breslow intermediate might function as a nucleophilic reagent by following two novel different pathways. |
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| Keywords: | Quinolin-4-one derivatives One-pot strategy Intra-Breslow intermediate Enol attack NHC-based enamine attack |
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