New 1,2,4 oxadiazolyl 1,3,5 triazines were synthesized from amidoximes derived from sym triazine mononitriles. The structure of one of the resulting compounds was studied in detail by X ray diffraction.Key words: amidoximes of the sym triazine series, 4,6 disubstituted 2 acetoxyamidino 1,3,5 triazines, 4,6 disubstituted 2 (5 methyl 1,2,4 oxadiazol 3 yl) 1,3,5 triazines, cy clization.1,2,4 Oxadiazole and sym triazine derivatives possess a wide spectrum of biological activities. 1-3 It was of inter est to synthesize new compounds containing both these heterocycles.We synthesized (Scheme 1) oxadiazolyltriazines 4 from nitriles 1. Amidoximes 2a-i were prepared by the reac tion of nitriles 1 with a 20% excess of hydroxylamine in an water ethanol solution.It is known 4,5 that the hydroxy group in aromatic amidoximes smoothly reacts with carboxylic acid an hydrides and chlorides to form the corresponding acylated derivatives. The reactions of compounds 2a-i with acetyl and isobutyroyl chlorides, which were used in a 5% excess with respect to the stoichiometric amount, under mild conditions (solutions in anhydrous benzene, 5-20 °C) in the presence of an excess of pyridine produced acylated derivatives 3a-m.Refluxing of solutions of compounds 3a-m in glacial acetic acid for 2-5 h smoothly afforded the correspond ing substituted 1,2,4 oxadiazolyl 1,3,5 triazines 4a-m in good yields.The crystal structure of one of the resulting oxa diazolyl 1,3,5 triazines, viz., compound 4d containing the amino and diethylamino groups at positions 4 and 6 of the triazine ring, was established by X ray diffraction study of a single crystal grown from ethanol. A projection of the crystal structure of compound 4d is shown in Fig.
