Some trans-phenylazo-1,2,4-oxadiazoles

Abstract

Some trans-phenylazoformamide oximes (4) have been prepared from trans-benzenediazocyanides (3) and hydroxylamine, and converted into trans-3-phenylazo-1,2,4-oxadiazoles (5) by reaction with amide acetals or trialkyl orthoformates. Some 5-unsubstituted 3-phenylazo-1,2,4-oxadiazoles have been reduced to 3-amino-1-aryl-1,2,4-triazoles (8), but di-imide reduced 3-p-chlorophenylazo-1,2,4-oxadiazole to the corresponding hydrazine. Thiocyanogen converted 5-methyl-3-phenylazo-1,2,4-oxadiazole into the corresponding p-thiocyanato-compound (5o).