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An easy to handle high-efficient approach to 5-polyfluoroalkyl-1,2,4-triazole-3-thiones (11 examples, up to 91% yield) is reported. The tautomerism of thione and thiol forms for the obtained products is discussed. A one step procedure for 6,6-dimethyl-3-(trifluoromethyl)-5,6-dihydro[1,3]thiazolo[2,3- c ][1,2,4]triazole formation from trifluoroacetic acid and 4-methallylthiosemicarbazide has been developed. The structures of the products were unambiguously determined by complex NMR investigation and by single crystal X-ray diffraction. [ABSTRACT FROM AUTHOR]

Abstract: Some new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(R)-2H-1,2,4-triazol-3(4H)-thiones 4a,b; 5a,b and 5-(4-(4-X-phenylsulfonyl)phenyl)-N-(R)-1,3,4-thiadiazol-2-amines 6a,b; 7a,b were obtained by cyclization of new N1-[4-(4-X-phenylsulfonyl)benzoyl]-N4-(R)-thiosemicarbazides 2a,b; 3a,b (X=H, Br). The 1,2,4-triazoles were synthesized by intramolecular cyclization of acylthiosemicarbazides, in basic media. On the other hand, 1,3,4-thiadiazoles were obtained from same acylthiosemicarbazides, in acidic media. These new intermediates from thiosemicarbazide class were afforded by the reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X=H, Br) 1a,b with 4-trifluoromethoxyphenyl or 3,4,5-trimethoxyphenyl isothiocyanate. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis. All the new compounds were screened for their antimicrobial activity against some bacteria (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 13061, Escherichia coli ATCC 25922, Enterobacter cloacae ATCC 49141, Acinetobacter baumannii ATCC 19606 and Pseudomonas aeruginosa ATCC 27853) and yeasts (Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019). [Copyright &y& Elsevier]

A simple approach involving refluxing appropriately disubstituted thiosemicarbazide 8 in presence of formic acid for the synthesis of 1, a potent azole antifungal agent, has been described. [ABSTRACT FROM AUTHOR]

Abstract: The electrochemical oxidation of N-thioamidohydrazone, 1, was undertaken at platinum electrode in acetonitrile containing lithium perchlorate as supporting electrolyte and monitored via cyclic voltammetry and controlled potential coulometry. An overall process consisting of an irreversible two electron transfer involving, in absence or presence of a base, deprotonation and intramolecular cyclization reactions enables the formation of 1,2,4-triazol-3-thione in a satisfactory yield. [Copyright &y& Elsevier]

Abstract: Reaction of 2-pyridine N-4 ethylthiosemicarbazone, HAm4E, with AgNO3 leads to the hexanuclear compound [Ag(E124tazt)]6 (1) (HE124tazt=4-ethyl-5-pyridin-2-yl-2,4-dihydro-[1,2,4]triazol-3-thione), the result of an oxidative cyclization of the starting thiosemicarbazone. All Ag atoms of [Ag(E124tazt)]6 are bridged through the six S atoms of the deprotonated E124tazt ligand to form two bridged Ag3S3 rings. Each silver atom exhibits a trigonal planar coordination geometry bonded to two thiolate S atoms and one N atom from the bidentate E124tazt ligand. The Ag⋯Ag distances are much shorter than the van der Waals’ radius sum for silver(I), suggesting binding interactions between the silver atoms, which were confirmed by means of DFT calculations. The X-ray single-crystal structural analysis reveals the arrangement of 1 as a two-dimensional (2D) network via π–π stacking interactions. Preliminary luminescence measurements have been carried out. [Copyright &y& Elsevier]