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有机化学 ›› 2004, Vol. 24 ›› Issue (11): 1396-1402. 上一篇    下一篇

研究论文

N-糖基-N-取代-氨基硫脲及N-糖基-N'-取代-联二硫脲类化合物的合成

连召斌a, 黄艳a, 曹玲华*,a,b   

  1. a新疆大学化学化工学院 乌鲁木齐 830046;
    b南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2004-01-05 修回日期:2004-04-12 接受日期:2004-05-07 发布日期:2022-09-21
  • 通讯作者: * E-mail: clhxj@xju.edu.cn
  • 基金资助:
    国家自然科学基金(No. 29962002)资助项目.

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

LIAN Zhao-Bina, HUANG Yana, CAO Ling-Hua*,a,b   

  1. aCollege of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046;
    bState Key Laboratory of Elemento-Organic Chemistry, Nankai University,Tianjin 300071
  • Received:2004-01-05 Revised:2004-04-12 Accepted:2004-05-07 Published:2022-09-21

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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-噁二唑(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, 1H NMR, MS谱和元素分析证实.IR谱中900 cm－1附近的吸收及1H NMR谱中偶合常数JCl—H=9～10 Hz,证明产物为β-构型.

关键词: 糖基异硫氰酸酯, 氨基硫脲, 联二硫脲, 合成

Aromatic 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), aseries 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 NMRand MS spectral data. The absorption around 900 cm－1 in IR spectra and coulpling constant JCl—H=9～10 Hz in 1H NMR spectra confirmed that all compounds have β-configuration.

Key words: glycosyl isothiocyanate, thiosemicarbazide, bithiourea, synthesis