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-alpha]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base
文献类型：期刊论文
| 作者 | Xu, Huayan; Luo, Xiaowei1; Wang, Junfeng1; Zhou, Xuefeng1; Yang, Bin1; Li, Ding2; Luo, Zaigang; Liu, Yonghong1; Liao, Shengrong1; Xu, Liang1 |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2019 |
| 卷号 | 75期号:19页码:2785 |
| 关键词 | Quinolin-4-one derivatives One-pot strategy Intra-Breslow intermediate Enol attack NHC-based enamine attack |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2019.03.058 |
| 英文摘要 | 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-alpha]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. (C) 2019 Published by Elsevier Ltd. |
| 源URL | [http://ir.scsio.ac.cn/handle/344004/17847]  |
| 专题 | 南海海洋研究所_中科院海洋生物资源可持续利用重点实验室 |
| 作者单位 | 1.Anhui Univ Sci & Technol, Coll Chem Engn, Huainan 232001, Peoples R China 2.Chinese Acad Sci, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, Res Ctr Marine Microbes,South China Sea Inst Ocea, Guangzhou 510301, Guangdong, Peoples R China 3.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xu, Huayan,Luo, Xiaowei,Wang, Junfeng,et al. 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-alpha]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base[J]. TETRAHEDRON,2019,75(19):2785, 2796. |
| APA | Xu, Huayan.,Luo, Xiaowei.,Wang, Junfeng.,Zhou, Xuefeng.,Yang, Bin.,...&Xu, Liang.(2019).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-alpha]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base.TETRAHEDRON,75(19),2785. |
| MLA | Xu, Huayan,et al."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-alpha]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base".TETRAHEDRON 75.19(2019):2785. |
入库方式： OAI收割
来源：南海海洋研究所
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