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Paper | Regular issue | Vol 55, No. 5, 2001, pp.905-924
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9173
■ 2,4,6-Tris(azol-1-yl)-1,3,5-triazines: A New Class of Multidentate Ligands

Viktor Milata, Rosa María Claramunt,* Pilar Cabildo, María Dolores Santa María, Pilar Cornago, Lourdes Infantes, Felix H. Cano, and Jose Elguero

*Departamento de Química Orgánica y Biologiá, Faclutade de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain

Abstract

The synthesis of thirteen tris(azol-1-yl)-s-triazines (azole = pyrazoles, imidazoles, 1,2,4-triazole and benzimidazoles) is described. Particularly interesting are the compounds derived from C-adamantylazoles (4-adamantylpyrazole, 2-adamantylimidazole and 2-adamantylbenzimidazole) because of their high lipophilicity. The crystal and molecular structures of 2,4,6-tris(2-phenylimidazol-1-yl)-1,3,5-triazine (6c) and 2,4,6-tris(2-phenylbenzimidazol-1-yl)-1,3,5-triazine (8c) have been determined by X-Ray analysis. The molecular structure can be described as a propeller taking into account the twists existing between the central ring and the substituents. The crystal structure of both compounds show a distorted hexagonal packing of chains. All trisazolyltriazines have been fully characterized by 1H-, 13C- and 15N-NMR spectroscopy. The 13C and 15N chemical shifts in CDCl3 and trifluoroacetic acid have been used to discuss the conformation and the site of protonation.