Application of the anionic homologous Fries-rearrangement to the synthesis of 3-alkylbenzofuran-2(3H)-ones

被引：5

作者：

Azzena, Ugo ^{[1
]}

Pisano, Luisa ^{[1
]}

Pittalis, Mario ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2008年 / 22卷 / 09期

关键词：

alkylation; benzofuran-2(3H)-ones; Fries rearrangement; metalation; organolithiums; regioselectivity;

D O I：

10.1002/aoc.1437

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We have developed an effective organometallic-based procedure allowing the employment of 2-methylphenols as easily available starting materials in the synthesis of 3-alkylbenzofuran-2(3H)-ones. The first step of this protocol, an anionic homologous Fries-rearrangement, afforded 2-(2-tert-butyidimethylsilyloxyaryl)acetamides, which were selectively metalated and monoalkylated at the benzylic position. Acidic work-up of crude products afforded the desired heterocycles in satisfactory overall yields. Copyright (C) 2008 John Wiley & Sons, Ltd.

引用

页码：523 / 528

页数：6

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