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

[1] QUINONE IMIDES .39. ADDUCTS OF QUINONE MONOIMIDES AND CONVERSION OF ACTIVE METHYLENE ADDUCTS TO BENZOFURANS [J].

ADAMS, R ;

WHITAKER, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (03) :658-663

[2] Lewis acid-catalyzed [4+2] benzannulation between enynal units and enols or enol ethers: Novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives [J].

Asao, Naoki ;

Aikawa, Haruo .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5249-5253

[3] Synthesis of [1,2,5]selenadiazolo[3,4-f]quinolone derivatives by the Gould-Jacobs reaction of 5-amino-2,1,3-benzoselenadiazole [J].

Bella, Maros ;

Schultz, Marcel ;

Milata, Viktor .

ARKIVOC, 2012, :242-251

[4] Site selectivity of the Diels-Alder reactions of 3-[1-(tert-butyldimethylsilyloxy)vin-1-yl]furan and 3-(propen-2-yl)furan. Synthesis of 4-substituted benzofurans [J].

Benitez, A ;

Herrera, FR ;

Romero, M ;

Talamas, FX ;

Muchowski, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1487-1492

[5] Recent Advances in Our Mechanistic Understanding of SNV Reactions [J].

Bernasconi, Claude F. ;

Rappoport, Zvi .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :993-1003

[6] Synthesis of Pyridin-2(1H)-one Derivatives via Enamine Cyclization [J].

Chikhalikar, Sandip ;

Bhawe, Vijay ;

Ghotekar, Bhausaheb ;

Jachak, Madhukar ;

Ghagare, Maruti .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) :3829-3836

[7] Facile two-step synthesis of 2-arylbenzofurans based on the selective cross McMurry couplings [J].

Duan, Xin-Fang ;

Zeng, Jing ;

Zhang, Zhan-Bin ;

Zi, Guo-Fu .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10283-10286

[8] Lewis acid-promoted reactions of 3-methoxy-N-(benzenesulfonyl)-1,4-benzoquinone monoimine with propenylbenzenes [J].

Engler, TA ;

Scheibe, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6247-6253

[9] Lewis acid-controlled regioselectivity in reactions of styrenyl systems with benzoquinone monoimides: New regioselective syntheses of substituted 2-aryl-2,3-dihydrobenzofurans, 2-aryl-2,3-dihydroindoles, and 2-arylindoles [J].

Engler, TA ;

Chai, WY ;

LaTessa, KO .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9297-9308

[10] STEREOSPECIFIC LEWIS ACID-PROMOTED REACTIONS OF STYRENYL SYSTEMS WITH 2-ALKOXY-(6-ALKYL)-1,4-BENZOQUINONES - SCOPE, LIMITATIONS, AND SYNTHETIC APPLICATIONS [J].

ENGLER, TA ;

COMBRINK, KD ;

LETAVIC, MA ;

LYNCH, KO ;

RAY, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6567-6587

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