Synthesis of 1, 3, 4-Oxadiazolin-2-ones by 1, 3-Dipolar Addition of Carbon Dioxide with Nitrile Imine

Abstract

The synthesis of 3, 5-diphenyl-and 5-tert-buthyl-3-phenyl-1, 3, 4-oxadiazolin-2-ones by the 1, 3-dipolar addition of carbon dioxide with nitrile imine was investigated. The 1, 3-dipolar addition was carried out at 60°C for 36h in a potable reactor (autoclave) into which the required amounts of dryice (carbon dioxide), N- (α-chloroalkylidene) -N'-phenylhydrazines, triethylamine or 1, 4-diazabicyclo- [2.2.2] octane and 1, 4-dioxane were placed, with a mechanical stirrer, to give 3, 5-diphenyl-1, 3, 4-oxadiazolin-2-one in a 25% yield and 3-phenyl-5-tert-butyl-1, 3, 4-oxadiazolin-2-one in a 14% yield.