Synthesis of some 1,2,4-triazoles and 1,2,4-triazolines by reaction of oxamidrazone condensation products with acetic anhydride

Abstract

Products of condensation of acetic anhydride with bisalkylideneamino-oxamidines are described. The bis(cyclopentylidene-, cycloheptylidene-, phenylethylidene-, and 1-methyl-2-phenylethylidene-amino)oxamidines gave substituted 5-methyl-1-vinyl-1,2,4-triazoles. Bis(allylidene-, cinnamylidene-, and 1,2-diphenylethylidene-amino)-oxamidines gave substituted 1,4-diacetyl-1,2,4-triazolines. Bis(adamantylidene- and 1,2-diphenylethylideneamino)oxamidines gave acetylated alkylideneamino-oxamidines. Bis(cyclohexylideneamino)oxamidine was anomalous in that it gave 1,1′-diacetyl-5,5′-dimethyl-3,3′-bi-1,2,4-triazole. Mechanisms of these reactions are discussed.