Solution-Phase Synthesis of a Diverse Library of Benzisoxazoles Utilizing the [3 + 2] Cycloaddition of in Situ-Generated Nitrile Oxides and Arynes
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- 作者：Anton V. Dubrovskiy ; Prashi Jain ; Feng Shi ; Gerald H. Lushington ; Conrad Santini ; Patrick Porubsky ; Richard C. Larock
- 刊名：ACS Combinatorial Science
- 出版年：2013
- 出版时间：April 8, 2013
- 年：2013
- 卷：15
- 期：4
- 页码：193-201
- 全文大小：595K
- 年卷期：v.15,no.4(April 8, 2013)
- ISSN：2156-8944
文摘
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.