One-pot sequential combination of multi-component and multi-catalyst: synthesis of 5-aminobenzofurans from aminophenol and ketene acetals

被引：16

作者：

Yang, Cheng-Wen ^{[1
]}

Bai, Yue-Xia ^{[1
]}

Zhang, Ni-Tao ^{[1
]}

Zeng, Cheng-Chu ^{[1
]}

Hu, Li-Ming ^{[1
]}

Tian, Hong-Yu ^{[2
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

[2] Beijing Technol & Business Univ, Sch Food Chem, Beijing 100048, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 49期

基金：

北京市自然科学基金;

关键词：

Multi-catalyst; Oxidation; Cyclization; 5-Aminobenzofurans; Alkene acetals; ACID-PROMOTED REACTIONS; ELECTROCHEMICAL SYNTHESIS; STYRENYL SYSTEMS; REGIOSELECTIVE SYNTHESES; ENOL ETHERS; DERIVATIVES; BENZOFURANS; S; N-ACETALS; IODINE; 2-ARYL-2,3-DIHYDROINDOLES;

D O I：

10.1016/j.tet.2012.09.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between p-aminophenols 1 and various ketene acetals 2 in the presence of hypervalent iodine is described. The results show that 2- and 3-substituted 5-sulfonamidobenzofurans 3 are obtained in moderate to good yields from p-aminophenols and ketene acetals. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：10201 / 10208

页数：8

共 41 条

[31] Electrochemical oxidation of catechols in the presence of ethyl-2-chloroacetoacetate. Synthesis and mechanistic study [J].

Shamsipur, Mojtaba ;

Davarani, Saied Saeed Hosseiny ;

Nematollahi, Davood .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (06) :1673-1677

[32]

SHEEN WS, 1994, PHYTOCHEMISTRY, V36, P213, DOI 10.1016/S0031-9422(00)97039-0

[33] Chemical constituents of Prangos tschimganica;: Structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity [J].

Shikishima, Y ;

Takaishi, Y ;

Honda, G ;

Ito, M ;

Takeda, Y ;

Kodzhimatov, OK ;

Ashurmetov, O ;

Lee, KH .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (07) :877-880

[34]

Singh O. M., 1997, J CHEM SO CP1, V23, P3561

[35] ELECTROCHEMICAL SYNTHESIS OF HETEROCYCLIC-COMPOUNDS .12. ANODIC-OXIDATION OF CATECHOL IN THE PRESENCE OF NUCLEOPHILES [J].

TABAKOVIC, I ;

GRUJIC, Z ;

BEJTOVIC, Z .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :635-638

[36] Efficient and practical route to α-aminocarbonylketene and α-cyanoketene dithioacetals [J].

Yin, Yanbing ;

Zhang, Qian ;

Liu, Qun ;

Liu, Yu ;

Sun, Shaoguang .

SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) :703-711

[37] A Facile Synthesis of α-Aryl α-Oxoheterocyclic Ketene N,N-Acetals Bearing an Electron-Rich Catechol Subunit-An Electrochemical Oxidative Approach [J].

Zeng, Cheng-Chu ;

Ping, Da-Wei ;

Xu, Yi-Sheng ;

Hu, Li-Ming ;

Zhong, Ru-Gang .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (33) :5832-5840

[38] One-Pot Electrochemical Synthesis of Fused Indole Derivatives Containing Active Hydroxyl Groups in Aqueous Medium [J].

Zeng, Cheng-Chu ;

Liu, Fu-Jian ;

Ping, Da-Wei ;

Hu, Li-Ming ;

Cai, Yuan-Li ;

Zhong, Ru-Gang .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6386-6389

[39]

Zhang F. M., 2010, CHIN J LIQUID CRYSTA, V1, P5

[40] Synthesis of BF2 complex of 3-methylthio enaminones [J].

Zhang, Ti ;

Jia, Yue-Mei ;

Yan, Sheng-Jiao ;

Yu, Chu-Yi ;

Huang, Zhi-Tang .

ARKIVOC, 2009, :156-170

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