Chemistry of aminophenols.: Part 3:: First synthesis of nitrobenzo[b]furans via a coupling-cyclization approach

被引：86

作者：

Dai, WM

Lai, KW

机构：

[1] Hong Kong Univ Sci & Technol, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Univ Sci & Technol, Inst Mol Technol Drug Discovery & Synth, Open Lab Chirotechnol, Kowloon, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 51期

关键词：

coupling reactions; benzofurans; phenols; aryl iodides;

D O I：

10.1016/S0040-4039(02)02333-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of 4-, 5-, and 6-nitrobenzo[b]furans has been achieved via the Sonogashira cross-coupling reaction of 2-iodonitrophenol acetates prepared from commercially available and inexpensive 2-aminonitrophenols. The obtained 2-alkynylnitrophenol acetates were subjected to a KO'Bu-promoted cyclization at room temperature to form nitrobenzo[b]furans. Examples of the synthesis of other substituted benzo[b]furans and the one-pot coupling-cyclization are given. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9377 / 9380

页数：4

共 59 条

[1] 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

[2] 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

[3] 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

[4] 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

[5]

BATES RW, 1995, SYNLETT, P1151

[6]

Bishop BC, 1997, SYNTHESIS-STUTTGART, P1315

[7]

Cagniant P., 1975, Adv. Heterocycl. Chem., V18, P337, DOI DOI 10.1016/S0065-2725(08)60132-4

[8]

CANDIANI I, 1993, SYNLETT, P269

[9]

Chilin A, 1998, SYNTHESIS-STUTTGART, P309

[10] Chemistry of aminophenols. Part 2: A general and efficient synthesis of indoles possessing a nitrogen substituent at the C4, C5, C6, and C7 positions [J].

Dai, WM ;

Sun, LP ;

Guo, DS .

TETRAHEDRON LETTERS, 2002, 43 (43) :7699-7702

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