Reaction of ?-arylacryloxiranes with phenyl azide. Synthesis and chemical transformations of ?-phenylamino-?-arylacrylyloxiranes

Abstract

The reaction of Β-arylacrylyloxiranes with phenyl azide by refluxing in dioxane or toluene leads to Β-phenylamino-Β-aryl-acrylyloxiranes. Epoxypropionyl- and Β-hydroxypropionyltriazoles are also isolated when the reaction is carried out in the dark without heating. It is shown that Β-phenylamino-Β-arylacrylyloxiranes undergo cyclization to 3(2H)-furanones in an acidic medium, whereas they are converted to 2,3-dihydro-4-pyridones under basic-catalysis conditions.