2-糖氨基-5-(3,4,5-三甲氧基苯基)-1,3,4-噁二唑/1,3,4-噻二唑的合成及其荧光性能  

Synthesis of 2-Glycosylamino-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole/1,3,4-thiadiazole and Their Fluorescent Properties

作　　者：俞玉明[1] 向静[1] 曹玲华[1] 

机构地区：[1]新疆大学化学化工学院,新疆乌鲁木齐830046

出　　处：《新疆大学学报（自然科学版）》2012年第1期89-93,共5页Journal of Xinjiang University(Natural Science Edition)

基　　金：国家自然科学基金(20462006);新疆植物资源与天然产物化学重点实验室资助项目

摘　　要：以没食子酸为原料,经甲醚化,酯化,肼解,得到中间体3,4,5-三甲氧基苯甲酰肼;然后与糖基异硫氰酸酯反应,制得N-糖基-N-3,4,5-三甲氧基苯甲酰氨基硫脲.将硫脲在醋酸汞/乙醇溶液或乙酸酐-磷酸体系中合环,分别得到了2-糖氨基-5-(3,4,5-三甲氧基苯基)-1,3,4-噁二唑/1,3,4-噻二唑.所有新化合物的结构均经IR,1H NMR和元素分析确证.化合物9,10的荧光测定结果显示,这些化合物都具有荧光特性,并探讨了化合物的结构对荧光性能的影响.The starting material gallic acid underwent methyl etherification, esteriflcation, hydrazinolysis to give intermediate 3,4,5-trimethoxybenzoyl hydrazine, and then reacted with glycosyl isothiocyanates to form N-glycosyl-N＇-3,4,5-trimethoxybenzoylthiosemicarbazides, then cyclization of the glycosyl-thioureas to yield 2-glycosylamino-5-（3,4,5-trimethoxyphenyl）-l,3,4-oxadiazoles in presence of Hg（OAc）2 or produced 2-glycosylamino-5-（3,4,5-trimethoxyphenyl）-l,3,4-thiadiazoles under acetic anhydride and phosphoric acid condition. The structures of all the synthesized compounds were confrmed by spectral data IR, 1H NMR and elemental analysis. The fluorescent spectra of compounds 9 and 10 were detected and showed that they had fluorescence. The effect of the structure of the compounds on fluorescent properties was also discussed.

关 键 词：没食子酸 糖基异硫氰酸酯 1 3 4-噁二唑 1 3 4-噻二唑 荧光性能 

分 类 号：O621.3[理学—有机化学]