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5-Furan-2-yl[1,3,4]oxadiazole-2-thiol (Ia) and 5-furan-2-yl-4H-[1,2,4]-triazole-3-thiol (Ib) were synthesized from furan-2-carboxylic acid hydrazide. Mannich basesand methyl derivatives were then prepared. The structures of the synthesized compoundswere confirmed by elemental analyses, IR and 1H-NMR spectra. Their thiol-thione tautomericequilibrium is described.

In this study appropriate hydrazide compounds, furan-2-carboxylic acidhydrazide (1) and phenylacetic acid hydrazide (2) were converted into 1,4-substitutedthiosemicarbazides 4a-e and 5a-e and 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7 and 10. The 1,4-substituted thiosemicarbazides were then converted into5-(furan-2-yl or benzyl)-4-(aryl)-4H-1,2,4-triazole-3-thiols 8a-e and 9a-e. In addition, theazomethines 11a-d and 12a-d were prepared from the corresponding arylaldehydes and the4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7 and 10. The structures of allthe synthesized compounds were confirmed by elemental analyses, IR, 1H-NMR and13 C-NMR spectra.