1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides under "Non-Conventional" Conditions: Green Solvents, Irradiation, and Continuous Flow.

Abstract

The 1,3-dipolar cycloaddition reactions (DCs) of nitrile oxides (NOs) to alkenes and alkynes are useful methods for the synthesis of 2-isoxazolines and isoxazoles respectively, which are important classes of heterocyclic compounds in organic and medicinal chemistry. Most of these reactions are carried out in organic solvents and under thermal activation. Nevertheless the use of supercritical carbon dioxide (scCO2 ) and ionic liquids (Ils) as alternative solvents and the application of microwave (MW) and ultrasound (US) as alternative activation procedures have evident advantages from the "Green Chemistry" point of view. The critical discussion on the applications of these "unconventional" activation methods and reaction conditions in the 1,3-DCs of NOs is the objective of the present Review.