Polymer-Supported Vinyl Sulfone as an Efficient Reagent for the Synthesis of 3-Monosubstituted Isoxazoles

Abstract

Polystyrene-supported vinyl sulfone reagent has been developed and used for solid-phase organic synthesis of 3-monosubstituted isoxazoles by 1,3-dipolar cycloaddition reaction with nitrile oxides and subsequent cleavage from the polymer support through an elimination reaction in the presence of potassium tert-butoxide. The advantages of this method include straightforward operation, good yield, and high purity of the crude products.

GRAPHICAL ABSTRACT

Keywords:

• 1,3-Dipolar cycloaddition
• elimination reaction
• 3-monosubstituted isoxazole
• polystyrene-supported vinyl sulfone
• solid-phase organic synthesis

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 21062007) and the Research Program of Jiangxi Province Department of Education (Nos. GJJ10385, GJJ10733, and GJJ11380).

Notes

^a Overall isolated yields based on polystyrene-supported vinyl sulfone 3.

^b Determined by HPLC of crude cleavage product.