Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives

A series of acylhydrazones (2a-f ) were synthesized by the condensation of iminoester hydrochlorides (1a-f ) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a,c,e) were obtained in the same reaction media. The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4- triazoles (4a-c). The acetylation of 4-amino-3,5-dialkyl-1,2,4-triazoles produced N-[3,5-dialkyl-4H- 1,2,4-triazol-4-yl] acetamides (5-7). The treatment of compounds 4a and 4c with various aromatic aldehydes resulted in the formation of 4-arylidenamino-3,5-dialkyl-1,2,4-triazoles (8a,d, e, and 10a-e). Sodium borohydride reduction of 4-arylidenamino derivatives afforded 4-alkylamino-3,5-dialkyl-1,2,4-triazoles (9a,d, e, and 11a-e). Compounds 4b, 4c, 7, 8d, and 11c showed good antifungal activity only against yeast-like fungi, while compounds 3e, 6, 8e, and 9e showed antimicrobial activity against bacteria and yeast-like fungi.