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A straightforward method has been developed for the synthesis of 1-phenyl-imidazo [2,1-c][1,2,4]triazole derivatives 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones derivatives 6a–g starting from 5-amino-1-phenyl[1,2,4]triazole and p-toluenesulfonic acid (PTSA). This methodology affords a number of 1-phenyl-imidazo [2,1-c][1,2,4]triazoles 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones 6a–g in reasonable yields and short reaction times. The structures of all new compounds were elucidated using infrared, 1H and 13C NMR, and high-resolution mass spectrometry. Some of the newly synthesized compounds were screened for their antimicrobial activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

A new 3-(5-alkyl-2-phenyl-2H-1,2,4-triazol-3-yl)thiazolidin-4-ones derivatives were obtained by condensation of 5-amino-1,2,4-triazoles, mercaptoacetic acid with aromatic aldehydes and catalyzed by Sm(SO3CF3)3 using microwave irradiation. The prepared compounds were tested for their antioxidant, antibacterial and antifungal proprieties. Some of these compounds displayed significant activities. Among them, compound 2e exhibited remarkable activity against a broad spectrum of Gram positive, negative bacteria and pathogenic fungal strains with low MIC values. The investigation of the mode of action of the most potent antifungal compounds on the fungus Pythium phanidermatum showed a membrane alteration and distortions of hyphal morphology. The newly synthesized compounds exhibited also promising radical scavenging activity.

International audience; The Groebke-type multicomponent reaction between 5-amino-1,2,4-triazole derivatives, aromatic aldehydes and isocyanides has been studied from the viewpoint of convenient generation of combinatorial arrays of imidazo[2,1-c][1,2,4]triazoles. The reaction is considered to proceed via the formation of an iminium species followed by a [4 + 1] cyclo addition with the isocyanides using scandium triflate as a Lewis acid catalyst. The synthesized imidazo[2,1-c][1,2,4]triazole derivatives 4a, 4b, 4f and 4g were screened for antibacterial, antifungal and antioxidant activities. Among the tested compounds, 4b followed by 4f showed potent antibacterial and antifungal activities. All of these compounds were also screened in vitro for the antioxidant activity using DPPH assay. Most of them have shown very significant antioxidant activity.

Compound (IIIc) is found to exhibit strong antibacterial and moderate antifungal activities.