Thermolysis of geminal diazides: A novel route to 1,3,4-oxadiazoles

Abstract

The geminal diazides ethyl a,a-diazidoacetoacetate and a,a-diazidobenzoylacetate were prepared from the corresponding dibromo precursors by nucleophilic azide displacement. Thermolysis of the diazido compounds led to the formation of 2,5-disubstituted 1,3,4-oxadiazoles in high yield.