Mercuric triflate catalyzed cycloisomerization of alkynyl-1,3-cyclohexanedione and alkynyl-1,3-cyclopentanedione

被引：17

作者：

Imagawa, H ^{[1
]}

Kotani, S ^{[1
]}

Nishizawa, M ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

来源：

SYNLETT | 2006年 / 04期

关键词：

mercuric triflate; catalytic cycloisomerization; alkynyl-1,3-cyclohexanediones;

D O I：

10.1055/s-2006-932464

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mercuric triflate was used to catalyze cycloisomerization of alkynyl-1,3-cyclohexanediones and cyclopentanediones to give fused oxabicyclic systems under mild reaction conditions with high catalytic turnover up to 1000 times.

引用

页码：642 / 644

页数：3

共 26 条

[1] THE PALLADIUM-CATALYZED SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS FROM 2-PROPARGYL-1,3-DICARBONYL COMPOUNDS AND VINYLIC OR ARYL TRIFLATES OR HALIDES [J].

ARCADI, A ;

CACCHI, S ;

LAROCK, RC ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1993, 34 (17) :2813-2816

[2] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[3] Developments in furan syntheses [J].

Brown, RCD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852

[4] Synthesis of 2,5-disubstituted furans via palladium-catalyzed annulation of alkyl 3-oxo-6-heptynoates [J].

Cacchi, S ;

Fabrizi, G ;

Moro, L .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5327-5332

[5] Synthesis of fused oxabicyclic systems by metal-catalyzed intramolecular addition of 1,3-cycloalkyldiones to alkynes [J].

Gulías, M ;

Rodríguez, JR ;

Castedo, L ;

Mascareñas, JL .

ORGANIC LETTERS, 2003, 5 (11) :1975-1977

[6] Biomimetic tandem cyclization catalyzed by Hg(OTf)2 affording polycarbocycles [J].

Imagawa, H ;

Iyenaga, T ;

Nishizawa, M .

SYNLETT, 2005, (04) :703-705

[7] Mercuric triflate-catalyzed tandem cyclization leading to polycarbocycles [J].

Imagawa, H ;

Iyenaga, T ;

Nishizawa, M .

ORGANIC LETTERS, 2005, 7 (03) :451-453

[8] Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-ones [J].

Imagawa, H ;

Kurisaki, T ;

Nishizawa, M .

ORGANIC LETTERS, 2004, 6 (21) :3679-3681

[9] FACILE SYNTHESIS OF 2,5-DISUBSTITUTED FURANS VIA PALLADIUM COMPLEX AND PERFLUORINATED RESINSULFONIC ACID-CATALYZED ISOMERIZATION DEHYDRATION OF ALKYNEDIOLS [J].

JI, JG ;

LU, XY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :764-765

[10] REGIOSELECTIVE SYNTHESIS OF HIGHLY SUBSTITUTED FURANS VIA TANTALUM ALKYNE COMPLEXES [J].

KATAOKA, Y ;

TEZUKA, M ;

TAKAI, K ;

UTIMOTO, K .

TETRAHEDRON, 1992, 48 (17) :3495-3502

← 1 2 3 →