ABSTRACT
Reaction of hydrazonoyl halides with 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and 2,3-diaminoquinazolin-4-one site-selectively afforded 3-substituted-7-(benzylidenamino)-1-phenyl-[1,2,4]triazolo[4,3-a]-pyrimidin-5(1H)-ones, [1,2,4,5]tetrazino[6,1-b]quinazolin-6(4H)-one, and 3-methyl-2-(4-substituted-phenylhydrazo)-[1,2,4]triazino[3,2-b]quinazolin-10-ones in good yields. The structures of the newly synthesized compounds were elucidated by chemical evidence and their IR, 1H, 13C NMR, and MS spectra. Furthermore, some of the products were screened against different strains of bacteria and fungi.
Subject(s)
Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Amines/chemistry , Anti-Infective Agents/chemical synthesis , Aspergillus flavus/drug effects , Candida albicans/drug effects , Chemistry Techniques, Synthetic , Drug Evaluation, Preclinical/methods , Escherichia coli/drug effects , Hydrazones/chemistry , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Staphylococcus aureus/drug effectsABSTRACT
Ribosylation of 3-methylthio-5-phenyl-1,2,4-triazole (1) with ribose derivative 2 gave the protected 1,2,4-triazole-nucleoside 3, which reacted with hydrazine hydrate to afford the 3-hydrazino-1,2,4-triazole derivative 5. Reaction of 5 with aromatic aldehydes yielded the corresponding hydrazones 6, which cyclized under bromination in acetic acid to give 8. Debenzoylation of 8 afforded novel 1,2,4-triazolo[3,4-c]-1,2,4-triazole nucleosides 9.