Synthesis And Characterization Of 3,3',5,5'-Tetraaryloxy (Tetraalkoxy)-4,4'-bi-1,2,4-triazole

4,4'-Bi-1,2,4-triazole(BTr), having two vertical N,N'-linked triazole rings, has made remarkable achievements in the fields of coordination chemistry, electrochemistry, pharmaceuticals, pesticides and energetic compounds. However, compounds containning BTr as basic skeleton were rarely reported. This dissertation aims at the synthesis of 3,3',5,5'-tetraaryloxy-4,4'-bi-1,2,4-triazole(2a-2j), 3,3',5,5'-tetramethoxy-4,4'-bi-1,2,4-triazole(3a) and 3,3',5,5'-tetrabenzyloxy-4,4'-bi-1,2,4-triazole(3b), the contents are as follows:1 Under the cesium carbonate as catalyst, nine 3,3',5,5'-tetraaryloxy-4,4'-bi-1,2,4-triazole were successfully synthesized via nucleophilic aromatic substitution(SNAr) with 3,3',5,5'-tetrchloro-4,4'-bi-1,2,4-triazole(TCBTr) as raw material. The novel title compounds were characterized by MS, 1H NMR, 13 C NMR, IR.2 Three single crystals of 3,3',5,5'-tetra(4-methoxyphenoxy)-4,4'-bi-1,2,4-triazole(CCDC: 1457106), 3,3',5,5'-tetra(2,5-dimethylphenoxy)-4,4'-bi-1,2,4-triazole(CCDC: 1457106) and 3,3',5,5'-tetra(4-chlorophenoxy)-4,4'-bi-1,2,4-triazole(CCDC: 1457106) were successfully cultivated via slowly evaporating solvent, obtaing the corresponding crystal measurement dates.3 The technological conditions of the synthesi s of 3,3',5,5'-tetraphenoxy-4,4'-bi-1,2,4-triazole were investigated. Through single factor, various parameters such as temperature, reaction time, raw material ratio, solvent, catalyst and desiccant were investigated. The generality of the optimal conditions in synthesis aromatic ether derivatives of 4,4'-bi-1,2,4-triazole(BTr) were determined.4 Under the above-mentioned optimal conditions, the reaction activity of TCBTr, 3,3',5,5'-tetrabromo-4,4'-bi-1,2,4-triazole(TBBTr) and 3,3',5,5'-tetraiodo-4,4'-bi-1,2,4- triazole(TIBTr) were studied and compared in SNAr reaction.5 The synthesis of 3,3',5,5'-tetraalkoxy-4,4'-bi-1,2,4-triazole were investigated with sodium methylate and phenylcarbinol as raw material respectively. The novel title compound 3,3',5,5'-tetramethoxy-4,4'-bi-1,2,4-triazole was successfully synthesized and characterized by MS, 1H NMR.6 The synthetic mechanism of nucleophilic aromatic substitution was affirmed by successfully explored the synthesis of 3,3',5,5'-tetraaryloxy(tetramethoxy)-4,4'-bi-1,2,4-triazole.