Expedited synthesis of benzofuran-2-carboxylic acids via microwave-assisted Perkin rearrangement reaction

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• 作者：Karla-Sue C. Marriott ; ^{marriottk@savannahstate.edu} ; Rena Bartee ; Andrew Z. Morrison ; Leonard Stewart ; Julian Wesby
• 关键词：Perkin rearrangement ; Halocoumarin ; Benzofuran-2-carboxylic acid ; Microwave ; Regioselective bromination
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：27 June, 2012
• 卷：53
• 期：26
• 页码：3319-3321
• 文件大小：347 K

摘要

3-Halocoumarins are readily converted into benzofuran-2-carboxylic acids via a Perkin (coumarin-benzofuran ring contraction) rearrangement reaction. This rearrangement entails initial base catalyzed ring fission. The resulting phenoxide anion then attacks a vinyl halide to produce the final benzofuran moiety. We explored this reaction under microwave reaction conditions and were able to significantly reduce reaction times as well as obtain very high yields of a series of benzofuran-2-carboxylic acid derivatives.