含氟肉桂醛与4-氨基-5-(3,4,5-三甲氧基苯基)-1,2,4-三唑-3-硫酮(2)缩合生成5-(3,4,5-三甲氧基苯基)-4-取代苯基烯丙亚胺基-1,2,4-三唑-3-硫酮(3), 再烷基化为新型含氟肉桂醛1,2,4-三唑亚胺(4). 化合物结构经1H NMR, 13C NMR, IR以及元素分析确认, 并用X-ray单晶衍射测定了化合物4g的晶体结构, 证实了分子中两个环外双键N=C和C=C均为E-式构型. 初步生物活性测试结果表明, 部分化合物具有抗植物病毒活性.
A series of 4-(substituted-3-phenylallyideneamino)-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione (3) were synthesized by condensation reaction of 4-amino-3-(3,4,5-trimethoxyphenyl)- 1H-1,2,4-triazole-5(4H)-thione (2) with various fluorocinnamaldehydes. Alkylation of 3 with alkyl halides afforded N-1,2,4-triazole moieties imines containing fluorocinnamylidene 4. Their structures were confirmed by 1H NMR, 13C NMR, IR and elemental analyses. The single crystal structure of compound 4g was deter- mined by X-ray diffraction analysis, which revealed that the two double bonds N=C and C=C outside the rings were of E,E-configurations. The preliminary bioassay showed that some of them exhibited moderate antiviral activity.