Parallel Synthesis of a Multi-Substituted Benzo[b]furan Library

被引：65

作者：

Cho, Chul-Hee ^{[1
]}

Neuenswander, Benjamin ^{[2
,3
]}

Lushington, Gerald H. ^{[2
,3
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Univ Kansas, NIH, Ctr Excellence Chem Methodol, Lawrence, KS 66047 USA

[3] Univ Kansas, NIH, Lib Dev, Lawrence, KS 66047 USA

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2008年 / 10卷 / 06期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/cc800120y

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The solution-phase parallel synthesis of a 121-member library of multi-substituted benzo[b]furans is described. 2.3,5-Trisubstituted benzo[b]furans have been prepared by the palladium-catalyzed substitution of 3-iodobenzofurans by Suzuki-Miyaura, carbonylative Suzuki, Sonogashira, Heck, and carboalkoxylation chemistry. The 3-iodobenzofurans are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with ICI.

引用

收藏

页码：941 / 947

页数：7

相关论文

共 56 条

[1] An improved method for the palladium-catalyzed amination of aryl iodides [J].

Ali, MH ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2560-2565

[2] 3-p-Toluoyl-2-[4′-(3-diethylaminopropoxy)-phenyl]-benzofuran and 2-[4′-(3-diethylaminopropoxy)-phenyl]-benzofuran do not act as surfactants or micelles when inhibiting the aggregation of β-amyloid peptide [J].

Allsop, D ;

Gibson, G ;

Martin, IK ;

Moore, S ;

Turnbull, S ;

Twyman, LJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (02) :255-257

[3] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].

Anderson, Kevin W. ;

Ikawa, Takashi ;

Tundel, Rachel E. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695

[4] A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Moro, L .

SYNLETT, 1999, (09) :1432-1434

[5] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[6] Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].

Arcadi, A ;

Cacchi, S ;

DelRosario, M ;

Fabrizi, G ;

Marinelli, F .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288

[7] Palladium-catalyzed synthesis of lipophilic benzo[b]furans from cardanol [J].

Bernini, Roberta ;

Cacchi, Sandro ;

De Salve, Ilse ;

Fabrizi, Giancarlo .

SYNTHESIS-STUTTGART, 2007, (06) :873-882

[8] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].

Buchwald, SL ;

Mauger, C ;

Mignani, G ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39

[9] Solid-phase synthesis of 2,3-dsubstituted benzo[b]thiophenes and benzo[b]selenophenes [J].

Bui, CT ;

Flynn, BL .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (02) :163-167

[10] 2-substituted-3-allenyl-benzo[b]furans through the palladium-catalysed cyclization of propargylic o-(alkynyl)phenyl ethers. [J].

Cacchi, S ;

Fabrizi, G ;

Moro, L .

TETRAHEDRON LETTERS, 1998, 39 (28) :5101-5104

← 1 2 3 4 5 6 →