利用原位生成的腈氧化物和芳炔的[3 + 2]环加成反应，在溶液相中合成了具有多种结构的苯并异恶唑文库。
Solution-phase synthesis of a diverse library of benzisoxazoles utilizing the [3 + 2] cycloaddition of in situ-generated nitrile oxides and arynes.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
ACS Comb Sci. 2013 Apr 8;15(4):193-201. doi: 10.1021/co300159g. Epub 2013 Mar 8.
Abstract
A library of benzisoxazoles has been synthesized by the [3 + 2] cycloaddition of nitrile oxides with arynes and further diversified by acylation/sulfonylation and palladium-catalyzed coupling processes. The eight key intermediate benzisoxazoles have been prepared by the reaction of o-(trimethylsilyl)aryl triflates and chlorooximes in the presence of CsF in good to excellent yields under mild reaction conditions. These building blocks have been used as the key components of a diverse set of 3,5,6-trisubstituted benzisoxazoles.
摘要
通过腈氧化物与芳炔的[3 + 2]环加成反应，合成了苯并异恶唑文库，并通过酰化/磺化和钯催化偶联过程进一步多样化。八元关键中间体苯并异恶唑通过邻-(三甲基甲硅烷基)芳基三氟甲磺酸酯和氯代肟在 CsF 存在下，在温和的反应条件下以良好至优异的收率制备。这些砌块已用作多种 3,5,6-三取代苯并异恶唑的关键组成部分。
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