Synthesis of Some Heterocyclic Compounds from Amidoxime and Imidate

Amidoxime (2) was prepared from the reaction of carbonitrile (1) with hydroxyl amine hydrochloride. Compound (2) treated with either acid chloride or anhydride at room temperature to obtain O-aroyl and O-acetyl amidoxime (3a-c). However, on heating compound (2), oxadiazole derivatives (4a-c) were obtained, respectively. 1,2,4-Oxadiazole-5-one (5) was obtained from the reaction of amidoxime with phosgene. Amidine (7) also prepared from imidiate reaction with ammonium chloride.
A number of heterocyclic compounds (8-10) were also prepared by the reaction of imidate (6) with either amino derivatives or azide. Imidate (6) was prepared from the reaction of carbonitrile with ethanol in the presence of hydrogen hydrochloride gas.