通过分子内环化/甲基化构建新型螺异恶唑啉
Construction of Novel Spiroisoxazolines via Intramolecular Cyclization/Methylation.
作者信息
Ellis Erick D, Xu Jianping, Valente Edward J, Hamme Ashton T
机构信息
Department of Chemistry & Biochemistry, College of Science, Engineering and Technology, Jackson State University, Jackson, MS 39217 USA.
出版信息
Tetrahedron Lett. 2009 Sep 30;50(39):5516-5519. doi: 10.1016/j.tetlet.2009.07.095.
Abstract
Improved yields for the syntheses of a variety of spiroisoxazolines were achieved through intramolecular cyclization/methylation reactions of functionalized 5,5-disubstituted isoxazolines in one reaction vessel. Aromatic ring containing nitrile oxides and disubstituted geminal alkenes reacted in a 1,3-dipolar fashion to afford the corresponding 5,5-isoxazoline. A comparison of the relative location of the nucleophile and electrophile on the isoxazoline and two different ester functional groups was performed in order to determine the best isoxazoline system for the intramolecular cyclization/methylation reaction.
摘要
通过在一个反应容器中对功能化的5,5-二取代异恶唑啉进行分子内环化/甲基化反应，实现了多种螺异恶唑啉合成产率的提高。含芳环的腈氧化物和二取代偕二烯烃以1,3-偶极方式反应，得到相应的5,5-异恶唑啉。为了确定分子内环化/甲基化反应的最佳异恶唑啉体系，对亲核试剂和亲电试剂在异恶唑啉上的相对位置以及两个不同的酯官能团进行了比较。
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