Synthesis of 3-Acetoxy Oxindole Derivatives via Metal-free PhI(OAc)_2 Mediated Oxidation of 3-Substituted Indoles

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• 英文论文题名：Synthesis of 3-Acetoxy Oxindole Derivatives via Metal-free PhI(OAc)_2 Mediated Oxidation of 3-Substituted Indoles
• 论文作者：Xiaoqian Zhao ; Chunni Zhou ; Xing Qu ; Liang Wang
• 英文论文作者：Xiaoqian Zhao ; Chunni Zhou ; Xing Qu ; Liang Wang ; Key Laboratory of Optoelectronic Chemical Materials and Devices ; Ministry of Education ; School of Chemical and Enviromental Engineering ; Jianghan University
• 年：2016
• 作者机构：Key Laboratory of Optoelectronic Chemical Materials and Devices,Ministry of Education,School of Chemical and Enviromental Engineering,Jianghan University;
• 英文论文关键词：indole ; iodobenzene diacetate ; metal-free ; oxindole
• 会议召开时间：2016-09-23
• 会议录名称：中部四省化学化工学会2016年学术年会摘要集
• 语种：英文
• 分类号：O626.13
• 学会代码：JXHX
• 会议名称：中部四省化学化工学会2016年学术年会
• 会议地点：中国江西南昌
• 主办单位：中国化学会湖北代表处
• 学会名称：江西省化学化工学会
• 页数：1
• 文件大小：170k
• 原文格式：D
• 会议级别：地方

摘要

3-hydroxy oxindoles and their derivatives are an important class of the privileged core structures that frequently occur in a large number of natural products,pharmaceuticals and synthetic building blocks for alkaloids such as convolutamydines A-E,donaxaridine,dioxbrassinine,welwitidolnone,and SM-130686.~1 Many synthetic methods have been developed for the construction of such compounds.~2 Here we would like to report a facile and straightforward method for the synthesis of 3-hydroxy oxindoles via the metal-free PhI(OAc)_2 mediated oxidation of 3-substituted indoles.~3 The experimental results demonstrate that both the electronic properties of the N-protecting groups of indoles and acidic medium play important roles in this process.
3-hydroxy oxindoles and their derivatives are an important class of the privileged core structures that frequently occur in a large number of natural products,pharmaceuticals and synthetic building blocks for alkaloids such as convolutamydines A-E,donaxaridine,dioxbrassinine,welwitidolnone,and SM-130686.~1 Many synthetic methods have been developed for the construction of such compounds.~2 Here we would like to report a facile and straightforward method for the synthesis of 3-hydroxy oxindoles via the metal-free PhI(OAc)_2 mediated oxidation of 3-substituted indoles.~3 The experimental results demonstrate that both the electronic properties of the N-protecting groups of indoles and acidic medium play important roles in this process.

引文

[1](a)B.S.Jensen,CNS Drug Rev.2006,8,353;(b)Y.Kamano,H.-P.Zhang,Y.Ichihara,H.Kizu,K.Komiyama,G.R.Pettit,Tetrahedron Lett.1995,36,2783;(c)T.Tokunaga,W.E.Hume,T.Umezome,K.Okazaki,Y.Ueki,K.Kumagai,S.Hourai,J.Nagamine,H.Seki,M.Taiji,H.Noguchi,R.Nagata,J.Med.Chem.2001,44,4641;(d)T.Tokunaga,W.E.Hume,J.Nagamine,T.Kawamura,M.Taiji,R.Nagata,Bioorg.Med.Chem.Lett.2005,15,1789.