Abstract Two synthetic approaches towards 4′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-carboxylic acid, a valuable organic ligand for the preparation of metal-organic frameworks, are reported. The first reaction sequence leading to the target compound comprises the iodination of [1,1′-biphenyl]-4-carboxylic acid, formation of the methyl ester of 4′-iodo-[1,1′-biphenyl]-4-carboxylic acid, nucleophilic substitution of iodine with cyano, ring closure of tetrazole, and hydrolysis of the ester function. The second synthetic pathway starts from 4-bromobenzonitrile, which is converted through Suzuki coupling with 4-carboxyphenylboronic acid into 4′-cyano-[1,1′-biphenyl]-4-carboxylic acid, which in turn leads to the desired compound after ring closure of tetrazole. All of the synthesized compounds have been fully characterized by IR and 1H- and 13C-NMR spectroscopy. Single crystal X-ray structures are reported for the target compound and for methyl esters of 4′-iodo-[1,1′-biphenyl]-4-carboxylic acid and 4′-cyano-[1,1′-biphenyl]-4-carboxylic acid. The target compound and the intermediates showed no antimicrobial activity against Escherichia coli, Staphylococcus aureus and Candida albicans.

中文翻译：

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4'-(2 H-四唑-5-基)-[1,1'-联苯]-4-羧酸：中间体的合成方法、单晶X射线结构和抗菌活性

摘要 报道了 4'-(2H-四唑-5-基)-[1,1'-联苯]-4-羧酸的两种合成方法，4'-(2H-四唑-5-基)-[1,1'-联苯]-4-羧酸是一种用于制备金属-有机骨架的有价值的有机配体。产生目标化合物的第一个反应序列包括[1,1'-联苯]-4-羧酸的碘化，4'-碘-[1,1'-联苯]-4-羧酸甲酯的形成酸、碘与氰基的亲核取代、四唑的闭环和酯官能团的水解。第二条合成途径从 4-溴苯甲腈开始，通过 Suzuki 与 4-羧基苯基硼酸的偶联转化为 4'-氰基-[1,1'-联苯]-4-羧酸，然后再生成所需的化合物四唑的闭环。所有合成的化合物都已通过 IR 和 1H-和 13C-NMR 光谱进行了充分表征。报告了目标化合物和 4'-碘-[1,1'-联苯]-4-羧酸和 4'-氰基-[1,1'-联苯]-的甲酯的单晶 X 射线结构4-羧酸。目标化合物和中间体对大肠杆菌、金黄色葡萄球菌和白色念珠菌没有抗菌活性。