The synthesis of new heterocyclic compounds containing 2-Heptyl-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-One Ring

Firstly, the new compound 4-amino-2-heptyl-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one (40) was synthesized by the reaction of 4-amino-3-methyl-4,5-dihydro-1H-1,2,4-triazole-5-one (39) with 1-bromoheptane. 4-{[(2-hydroxy-5-substitutedphenyl)methylene] amino}-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-ones (54-58) obtained by treatment of compound 40 with benzaldehydes. Secondly, the new compound 2-heptyl-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one (41) was prepared by treatment of compound 40 in the presence of hypophosphorous acid and sodium nitrite. Then by the reaction of compound 41 with some benzyl halides obtained 4-(4-substitutedbenzyl)-2-heptyl-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-ones (64-67). Thirtly, Treatment of compound 41 with ethyl bromoacetate obtained 2-(1-heptyl-3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazole-4-yl] acetate (83), which was converted into 2-(1-heptyl-3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazole-4-yl) acetohydrazide (84) by treatment with hydrazine hydrate. Finally, synthesized compound 84 by the treatment of some aromatic aldehydes gave 2-(1-heptyl-3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazole-4-yl)-N'-[(2-hydroxy-5-substitutedphenyl)methylene] acetohydrazide (85-89) derivatives. The structures of 17 original compounds were identified by using IR, 1H NMR, 13C NMR and Mass spectroscopic data.