Efficient synthesis of furan-2-ylacetates, 7-(alkoxycarbonyl)benzofurans, and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans based on cyclization reactions of free and masked dianions: A "cyclization/dehydrogenation" strategy

被引：13

作者：

Bellur, E

Langer, P

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany

[3] Univ Rostock, Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 24期

关键词：

D O I：

10.1021/jo051767i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of furan-2-ylacetates have been prepared by dehydrogenation of monocyclic 2-alkylidene-tetrahydrofurans, which are readily available by cyclizations of open-chained 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane. 5'H-[2,3']Bifuranyl-2'-ones are available based on sequential "cyclization/dehydrogenation" reactions of alpha-acetyl-gamma-butyrolactones. A variety of 7-(alkoxycarbonyl)-benzofarans and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans were prepared by a cyclization/ dehydrogenation strategy. These reactions rely on cyclizations of 2-oxocycloalkane-1-carboxylate/derived 1,3-dicarbonyl dianions ("free dianions") or 1,3-bis-silyl enol ethers ("masked dianions") with various 1,2-dielectrophiles.

引用

页码：10013 / 10029

页数：17

共 65 条

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