Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones

被引：201

作者：

Kel'in, AV ^{[1
]}

Gevorgyan, V ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 01期

关键词：

D O I：

10.1021/jo010832v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

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页码：95 / 98

页数：4

相关论文

共 29 条

[1] ISOCYTOSINE H2-RECEPTOR HISTAMINE-ANTAGONISTS .3. THE SYNTHESIS AND BIOLOGICAL-ACTIVITY OF LUPITIDINE (SK-AND-F-93479) AND RELATED-COMPOUNDS [J].

BROWN, TH ;

ARMITAGE, MA ;

BLAKEMORE, RC ;

BLURTON, P ;

DURANT, GJ ;

GANELLIN, CR ;

IFE, RJ ;

PARSONS, ME ;

RAWLINGS, DA ;

SLINGSBY, BP .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1990, 25 (03) :217-226

[2]

EBERBACH WF, 1994, HOUBENWEYL, P16

[3] An efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-en-4-yn-1-ols [J].

Gabriele, B ;

Salerno, G ;

De Pascali, F ;

Costa, M ;

Chiusoli, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7693-7699

[4] A general and facile synthesis of substituted furans by palladium-catalyzed cycloisomerization of (Z)-2-En-4-yn-1-ols [J].

Gabriele, B ;

Salerno, G ;

Lauria, E .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7687-7692

[5] Synthesis of aromatic heterocycles [J].

Gilchrist, TL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20) :2849-2866

[6] Regioselective syntheses of substituted furans [J].

Hou, XL ;

Cheung, HY ;

Hon, TY ;

Kwan, PL ;

Lo, TH ;

Tong, SY ;

Wong, HNC .

TETRAHEDRON, 1998, 54 (10) :1955-2020

[7] Direct alkynyl group transfer from silicon to copper: New preparation method of alkynylcopper (I) reagents [J].

Ito, H ;

Arimoto, K ;

Sensui, H ;

Hosomi, A .

TETRAHEDRON LETTERS, 1997, 38 (22) :3977-3980

[8] ACYLATION REACTIONS OF SILYLATED BUTADIYNES - SYNTHESIS OF SOME NATURALLY-OCCURRING DIACETYLENIC KETONES [J].

JONES, GE ;

HOLMES, AB .

TETRAHEDRON LETTERS, 1982, 23 (31) :3203-3206

[9]

Kang SK, 1997, SYNTHESIS-STUTTGART, P874

[10] A novel Cu-assisted cycloisomerization of alkynyl imines: Efficient synthesis of pyrroles and pyrrole-containing heterocycles [J].

Kel'in, AV ;

Sromek, AW ;

Gevorgyan, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :2074-2075