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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
Xu, Huayan; Xu, Liang1; Luo, Xiaowei1; Wang, Junfeng1; Zhou, Xuefeng1; Yang, Bin1; Li, Ding2; Luo, Zaigang; Liu, Yonghong1; Liao, Shengrong1
2019
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume75Issue:19Pages:2785
AbstractA 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.
DepartmentLMB
KeywordQuinolin-4-one derivatives One-pot strategy Intra-Breslow intermediate Enol attack NHC-based enamine attack
DOI10.1016/j.tet.2019.03.058
Citation statistics
Document Type期刊论文
Identifierhttp://ir.scsio.ac.cn/handle/344004/17847
Collection中科院海洋生物资源可持续利用重点实验室
Affiliation1.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
Recommended Citation
GB/T 7714
Xu, Huayan,Xu, Liang,Luo, Xiaowei,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.,Xu, Liang.,Luo, Xiaowei.,Wang, Junfeng.,Zhou, Xuefeng.,...&Liao, Shengrong.(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.
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