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The behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one towards the active electrophilic compounds in polar and/ or non-polar solvents and various times and temperatures, has been studied. N -[2-(3-(3/5-(4-Nitrophenyl)-5/3-thioxo-1 H -1,2,4-triazol-1-yl)-5-oxo-1,2,4-triazin-6-yl)phenyl]pivalamides were obtained from the reaction of N -(2-(3-hydrazineyl-5-oxo-1,2,4-triazin-6-yl)phenyl)-pivalamide with 4-nitrobenzoyl isothiocyanate in THF and/ or EtOH-piperidine respectively. Also, N -(2-(3-hydrazineyl-5-oxo-1,2,4-triazin-6-yl)phenyl)-pivalamide was shown a strong nucleophilic behavior by reaction with N -phenyl-thiourea to produceÂ  N -[2-(5-oxo-3-(2-(phenylcarbamothioyl)-hydrazineyl)-1,2,4-triazin-6-yl)phenyl]pivalamide, which upon cyclization with diethyl carbonate produced N -(2-(5-oxo-3-(5-oxo-4-phenyl-3-thioxo-1,2,4-triazolidin-1-yl)- 1,2,4-triazin-6-yl)phenyl)pivalamide. Moreover, N -(2-(3-hydrazineyl-5-oxo-1,2,4-triazin-6-yl)phenyl)pivalamide studied its behavior by reaction with cyanoacetic acid, chloroacetonitrile, and/ or benzoyl carbonitrile to produce N -(2-(3-amino-4,8-dioxo-4 H -[1,2,4]triazino[4,3- b ][1,2,4]triazin-7-yl)phenyl)pivalamide, N -(2-(4-amino-8-oxo-2 H -[1,2,4]triazino[4,3- b ][1,2,4]triazin-7-yl)phenyl)pivalamide and N -(2-(4-imino-8-oxo-3-phenyl-4 H -[1,2,4] triazino [4,3- b ][1,2,4]triazin-7-yl)phenyl)pivalamide. Structure of the products was established upon their elemental analysis and FT-IR, 1 H/ 13 C NMR, and MS. The new compounds were evaluated as antibacterial agents some Gram-positive and negative bacteria. Some compounds were showed the highest inhibition activity towards Pseudomonas aeruginosa , Bacillus subtilis , Bacillus cereus , and Sarcina lutea bacteria and lowest inhibitory activity against Escherichia coli bacteria.

Behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one as a strong nucleophile towards active electrophilic compounds and their antibacterial evaluation