Synthesis of some 5-nitrofuran derivatives like as anti bacterial drugs in animals

Reaction of 5-nitrofuran-2-aldehyde 2 with 4-substituted-1,2-phenylendiamine 1a-b, naphthalene-1,8-diamine 4 and 2-hydroxy aniline 6 in water in the present of ferric ammonium sulfate (NH4Fe(SO4)2), obtained 6-substituted-2-(5-nitro-furan-2-yl)-1H-benzimidazole 3a-b, 2-(5-nitro-furan-2-yl)-1H-perimidine 5 and 2-(5-nitro-furan-2-yl)-benzoxazole 7 respectively, in good yields. Reaction of 5-nitrofuran-2-aldehyde with 4-amino-3-hydrazino-5-mercapto-1,2,4-triazol under reflux condition gave 4-amino-5-[Nʹ-(5-nitro-furan-2-yl-methylene)-hydrazino]-4H-[1,2,4]triazole-3-thiol 9. Compound 9 was reacted with terphthaluic acid and dimethyl acetylendicarboxylate (DMAD) to obtain Bis{6-yl-3-hydrazon-(2-yl-5-nitrofurfural)-1,2,4-triazol [3,4-b]1,3,4-thiadiazole}terphtaloyl 11 and 1,2,4-triazino[3,4-b]1,2,4-thiadiazine-7-one-3-hydrazon92-yl-5-nitrofurfural)6-exomethylenmethyl carboxylate 10 in good yields, respectively. The structures of these compounds were distinguished by 1H NMR, 13C NMR, IR, Mass spectra and microanalysis.