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Synfacts 2006(10): 1080-1080  
DOI: 10.1055/s-2006-949294
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of 3-Substituted Isoxazoles

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
S.-R. Sheng*, Q. Xin, X.-L. Liu, W.-K. Sun, R. Guo, X. Huang
Jiangxi Normal University, Nanchang and Zhejiang University, Hangzhou, P. R. of China
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

A simple method for preparation of 3-substituted isoxazoles by polystyrene-supported vinyl selenide was developed. Thus, polystyrene-supported selenenyl bromide 1 was prepared according to the reported procedures (K. C. Nicolaou et al. Chem. Commun. 1998, 1947-1948). The reaction of resin 1 with ethylene in THF followed by treatment with t-BuOK in THF gave vinyl selenide resin 2. The [3+2] cycloaddition reactions of resin 2 with nitrile oxides generated in situ from oximes 3, NCS, and Et3N afforded the corresponding polymeric isoxazoles 4. Treatment of resin 4 with H2O2 gave 3-substituted isoxazoles 5a-j (10 examples, 78-88% yield with purities >95% from 2).