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以对甲基苯胺为原料,经过重氮化反应生成对甲基叠氮苯(1).在强碱性条件下,1分别与氰基乙酸乙酯、氰基乙酰胺反应,制得中间体1-对甲苯基-5-氨基-1,2,3-三唑甲酸乙酯(2)和1-对甲苯基-5-氨基-1,2,3-三唑甲酰胺(5);中间体2经水解生成1-对甲苯基-5-氨基-1,2,3-三唑甲酸(3),进而在弱酸性条件下与取代苯甲醛反应得到6个未见文献报道的目标化合物1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酸(4a～4f),5与取代苯甲醛反应得到6个未见文献报道的目标化合物1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酰胺(6a～6f),化合物的结构均经IR,1H NMR,13C NMR确证.初步生物测试表明,12个化合物均表现出良好的抑菌活性,其中化合物4d～4f和6d～6f对金黄色葡萄球菌、白色念球菌的最小抑菌浓度(MIC)值为2～8μg/mL,抗菌效果优于氟康唑和三氯生.
To p-methylaniline as raw material, after diazotization reaction of methyl azidobenzene (1) under strong alkaline conditions, respectively, cyanoethyl acetate, cyanoacetamide reaction intermediates (2) and 1-p-tolyl-5-amino-1,2,3-triazolecarboxamide (5) The hydrolysis of body 2 gave 1-p-tolyl-5-amino-1,2,3-triazolecarboxylic acid (3) which was then reacted with substituted benzaldehyde under weakly acidic conditions to obtain 6 unreported target compounds 1 (4a ~ 4f), p-tolyl-5-substituted phenylimino-1,2,3-triazolecarboxylic acid and the reaction of 5 with substituted benzaldehyde gave 6 new target compounds, The structures of the compounds were confirmed by IR, 1H NMR and 13C NMR.A preliminary biological test showed that all of the 12 compounds The antibacterial activity of compound 4d ~ 4f and 6d ~ 6f against Staphylococcus aureus and Candida albicans was 2 ~ 8μg / mL, the antibacterial effect was superior to that of fluconazole and tris Chlorine Health.