A convenient procedure for the regioselective preparation of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium 10 and [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium salts 9 via regioselective electrophilic cyclization of 3-[(2-alken-1-yl)sulfanyl]-4H-1,2,4-triazoles 3 is reported. Direction of electrophilic heterocyclization strongly depends on nature of the alkenyl substitutent.

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Background: Condensed triazoles are a well-known class of heterocyclic compounds due to a wide range of biological activity. The study is dedicated to the evaluation of the antimicrobial potential of new functional derivatives of thiazolo[2,3-c][1,2,4]triazoles. Methods: Effective, easy-to-implement and low-cost routes to the production of title compounds via electrophilic intramolecular heterocyclization are reported. Bactericidal and fungicidal activities against Gram-positive and Gram-negative bacteria, and fungus were studied. The influence of functional groups on the biological activity of tested thiazolo[2,3-c][1,2,4]triazoles is discussed. Results: Microbiological evaluation shows that 6-[(trichlorotellanyl)methyl]-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-amine hydrogen chloride 2a and 3-(2-hydroxyphenyl)-6-[(trichloro-λ4-tellanyl)methyl]-5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazole 2g have a high bactericidal activity and Cu (I) salts of 3-(2-hydroxyphenyl)-6-iodomethyl/6-methylidene-5,6-dihydro-[1,3]thiazolo-[2,3-c][1,2,4]triazoles 5a,c have a high fungicidal activity. Conclusion: it must be concluded that these products or their derivatives may be of practical benefit as bactericidal and fungicidal agents.