Solid phase synthesis of isoxazole and isoxazoline-carboxamides via [2+3]-dipolar cycloaddition using resin-bound alkynes or alkenes

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• 作者：Sureshbabu Dadiboyena^a ; Adel Nefzi^a ; ^b ; ^{anefzi@tpims.org} ; ^{adeln@tpims.org}
• 关键词：Isoxazoles ; Isoxazolines ; Heterocycles ; 1 ; 3-Dipolar cycloadditions ; Solid phase synthesis ; Combinatorial chemistry
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：18 April, 2012
• 卷：53
• 期：16
• 页码：2096-2099
• 文件大小：256 K

摘要

An efficient approach for the parallel solid phase synthesis of isoxazole and isoxazoline derivatives has been developed. The isoxazoles and isoxazolines were constructed through a 1,3-dipolar cycloaddition reaction of nitrile oxides, with resin-bound alkynes or alkenes. The cycloaddition reaction conditions performed on solid phase supports was optimized, and an array of resin-bound carboxylic acid building blocks was utilized for distinct conversions. This methodology presents a new alternative to the diversity oriented synthesis of disubstituted isoxazoles and isoxazolines different from existing routes which are limited in structural diversity.