Palladium-catalyzed cyclization reactions of propargylic carbonates with nucleophiles: a methodology for the syntheses of substituted 2,3-dihydrofurans and benzofurans

被引：43

作者：

Yoshida, M ^{[1
]}

Morishita, Y ^{[1
]}

Fujita, M ^{[1
]}

Ihara, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 18期

基金：

日本学术振兴会;

关键词：

palladium; cyclization; dihydrofurans; phenols;

D O I：

10.1016/j.tet.2005.02.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenoxy-substituted 2,3-dihydrofurans were synthesized by the palladium-catalyzed reaction of 5-methoxycarbonyloxy-3-pentyn-1-ol with phenols. The propargylic carbonate containing a nucleophilic phenoxy group also reacted in the presence of palladium to produce the product. The reaction of 1-(2-hydroxyphenyl)-3-methoxycarbonyloxy-1-propyne with 2-methyl-1,3-cyclohexanedione or 2-methyl-1,3-cycohexanedione yielded the substituted benzofurans. The propargylic compound having a acetoxy group as a leaving group exhibited similar reactivity. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4381 / 4393

页数：13

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