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Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles | |
2016-07-04 | |
发表期刊 | CHEMISTRY-A EUROPEAN JOURNAL (IF:3.9[JCR-2023],4.1[5-Year]) |
ISSN | 0947-6539 |
卷号 | 22期号:28页码:9797-9803 |
发表状态 | 已发表 |
DOI | 10.1002/chem.201601185 |
摘要 | An efficient and highly regioselective iron(III)-catalyzed Friedel-Crafts-type arylation of spiro-epoxyoxindoles with phenols was developed for rapid access to 3-(3-indolyl)-oxindole-3-methanols, which could be further elaborated into benzofuranyl-spirooxindoles under Mitsunobu conditions. When spiro-epoxyoxindoles were reacted with naphthols in the presence of a catalytic amount of FeCl3 center dot 6H(2)O in dichloromethane, they underwent a tandem Friedel-Crafts-type arylation and O-cyclization to yield novel naphthofuranyl-spirooxindoles in excellent yields. This method is applied to enable the efficient and highly regioselective synthesis of a small-molecule inhibitor of the sodium channel Na(v)1.7 (+/-)-XEN402, which is currently in a phase IIb clinical trial for the treatment of pain. |
关键词 | cyclization epoxide iron oxindole spiro compounds |
收录类别 | SCI ; IC ; EI |
语种 | 英语 |
资助项目 | Strategic Priority Research Program of the Chinese Academy of Sciences[XDA01040302] |
WOS研究方向 | Chemistry |
WOS类目 | Chemistry, Multidisciplinary |
WOS记录号 | WOS:000380271400046 |
出版者 | WILEY-V C H VERLAG GMBH |
EI入藏号 | 20162402485144 |
EI主题词 | Aromatic compounds ; Catalysis ; Chemical reactions ; Cyclization ; Dichloromethane ; Iron ; Iron compounds ; Phenols ; Sodium ; Synthesis (chemical) |
WOS关键词 | ENANTIOSELECTIVE TOTAL-SYNTHESIS ; GROWTH-HORMONE SECRETAGOGUES ; GARDNERIA-MULTIFLORA MAKINO ; RING-OPENING REACTIONS ; LEWIS-ACID ; DIASTEREOSELECTIVE SYNTHESIS ; ASYMMETRIC-SYNTHESIS ; RADICAL ARYLATION ; 3+2 CYCLOADDITION ; INDOLE ALKALOIDS |
原始文献类型 | Article |
引用统计 | 正在获取...
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文献类型 | 期刊论文 |
条目标识符 | https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/1783 |
专题 | 生命科学与技术学院 生命科学与技术学院_特聘教授组_魏万国组 生命科学与技术学院_硕士生 生命科学与技术学院_博士生 |
通讯作者 | Wei, Wanguo |
作者单位 | 1.Chinese Acad Sci, Shanghai Adv Res Inst, 99 Haike Rd, Shanghai 201210, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.ShanghaiTech Univ, Sch Life Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China |
第一作者单位 | 生命科学与技术学院 |
通讯作者单位 | 生命科学与技术学院 |
推荐引用方式 GB/T 7714 | Luo, Mupeng,Yuan, Rongju,Liu, Xuesong,et al. Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles[J]. CHEMISTRY-A EUROPEAN JOURNAL,2016,22(28):9797-9803. |
APA | Luo, Mupeng,Yuan, Rongju,Liu, Xuesong,Yu, Linqian,&Wei, Wanguo.(2016).Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles.CHEMISTRY-A EUROPEAN JOURNAL,22(28),9797-9803. |
MLA | Luo, Mupeng,et al."Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles".CHEMISTRY-A EUROPEAN JOURNAL 22.28(2016):9797-9803. |
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