New 2-amino-[1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium hexabromotellurates: Experimental and computational structural studies

• Published in: Journal of molecular structure 2024-01, Vol.1295, p.136632, Article 136632
• Main Authors: Fizer, Oksana, Dujnič, Viera, Sidey, Vasyl, Baumer, Vjacheslav, Slivka, Mikhailo, Fizer, Maksym
• Format: Article
• Language: English
• Subjects: 1,2,4-triazole; 1,3-thiazole; Cyclization; Hexabromotellurate; Methallyl; Perovskite
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.136632

•Hexabromotelluric acid causes cyclization of methallyl thioether of a 1,2,4-triazole.•[1,3]Thiazolo[3,2-b][1,2,4]triazol-7-ium hexabromotellurates were synthesized.•Ab initio calculations explain the experimentally observed regioselectivity.•The synthesized salt's structure can be classified as a zero-dimensional perovskite.•Docking study points out that the synthesized cations are potential glioma inhibitors. The reaction of methallyl thioethers of a polysubstituted 5-amino-1,2,4-triazole-3-thiones with hexabromotelluric acid leads to the formation of a new hybrid hexabromotellurates containing the [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium cations. The annulation of the thiazoline ring undergoes through the proton-induced electrophilic cyclization of the methallyl thioether fragment. The structure analysis indicates that the newly synthesized 6,6-dimethyl-3-phenyl-2-(phenylamino)-5,6-dihydro-3H-[1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium hexabromotellurate has a zero-dimensional perovskite-type structure. Theoretical quantum chemical modeling of the proposed mechanisms explains the preferable formation of the five-membered thiazoline ring. Bioactivity of the [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium cation was investigated using molecular docking. [Display omitted]