A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide

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• 作者：Vinod Kumar and M.P. Kaushik
• 关键词：N-tert-Butyl-N-chlorocyanamide ; Aldoximes ; Hydroximoyl chlorides ; N-Phenylmaleimide ; Dipolarophiles ; 2-Isoxazolines
• 刊名：Tetrahedron Letters
• 出版年：2006
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：27 February 2006
• 卷：47
• 期：9
• 页码：1457-1460
• 文件大小：105 K

摘要

Treatment of aldoximes with N-tert-butyl-N-chlorocyanamide gave hydroximoyl chlorides in quantitative yields in less than a minute, which on dehydrohalogenation in the presence of triethylamine gave the corresponding nitrile oxides. The nitrile oxides underwent 1,3-dipolar addition to dipolarophiles and gave 2-isoxazolines in excellent yields under mild conditions.