N-糖基-2-取代-氨基硫脲及N-糖基-N′-取代-联二硫脲类化合物的合成  

Synthesis of N-Glycosyl-2-substituted-thiosemicarbazide and N-Glycosyl-N′-substituted-bithiourea Derivatives

作　　者：连召斌[1] 黄艳[1] 曹玲华[1] 

机构地区：[1]新疆大学化学化工学院,乌鲁木齐830046

出　　处：《有机化学》2004年第11期1396-1402,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金 (No.2 9962 0 0 2 )资助项目

摘　　要：芳香酸经酯化、肼解 ,合环后再引入肼基 ,得 2 肼基 5 芳基 1,3 ,4 二唑 ( 2 ) ,芳基硫脲经环化、肼解得 2 肼基 4/ 6 取代 -苯并噻唑 ( 3 ) .糖基异硫氰酸酯 ( 1)分别与 2 ,3及N 取代氨基硫脲 ( 4 )发生亲核加成反应 ,制得系列新的N 糖基 2 取代 -氨基硫脲衍生物 5 ,6及N 糖基 N′ 取代 -联二硫脲类化合物 7.所有化合物的结构均经IR ,1HNMR ,MS谱和元素分析证实 .IR谱中 90 0cm-1附近的吸收及1HNMR谱中偶合常数JCl—H=9～ 10Hz ,证明产物为 βAromatic acid underwent esterification, hydrazinolysis, cyclization and then introduction of hydrazino group again to give 2-hydrazino-5-aryl-1,3,4-oxadiazoles (2). Aryl thiourea underwent cyclization and hydrazinolysis to give 2-hydrazino-4/6-substituted benzothiazoles (3). After nucleophilic addition of glycosyl isothiocyanate (1) to 2, 3 and N-substituted thiosemicarbazides (4), a series of novel N-glycosyl-2-substituted-thiosemicarbazide and N-glycosyl-N′-substituted-bithiourea derivatives have been synthesized. The structures of the compounds were established on the basis of IR, 1H NMR and MS spectral data. The absorption around 900 cm -1 in IR spectra and coulpling constant J Cl—H=9～10 Hz in 1H NMR spectra confirmed that all compounds have β-configuration.

关 键 词：氨基硫脲 联二硫脲 合成 芳香酸 糖基异硫氰酸酯 β-构型 生物活性 

分 类 号：O621[理学—有机化学]