Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles

doi:10.1002/chem.201601185

	Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles
	Luo, Mupeng1,2,3 ; Yuan, Rongju1,2,3 ; Liu, Xuesong 1; Yu, Linqian 1; Wei, Wanguo1,2,3
	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...
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.