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

TETRAHEDRON LETTERS

卷:53

Article

Dadiboyena, Sureshbabu¹  Nefzi, Adel^1,2 

[1] Torrey Pines Inst Mol Studies, Port St Lucie, FL 34987 USA

[2] Florida Atlantic Univ, Boca Raton, FL 33431 USA

关键词: Isoxazoles;    Isoxazolines;    Heterocycles;    1,3-Dipolar cycloadditions;    Solid phase synthesis;    Combinatorial chemistry;   

DOI  :  10.1016/j.tetlet.2012.02.041

来源: Elsevier

【 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. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

Free