SIOC English
有机化学
高级检索

有机化学 ›› 2010, Vol. 30 ›› Issue (05): 703-706. 上一篇    下一篇

研究论文

区域选择性合成2-取代磺酰基亚肼基-3-全乙酰糖基-2,3-二氢噻唑及其表征、生物活性研究

王浩安，李玉新，李一鸣，王素华，李正名*   

  1. (南开大学元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2009-08-10 修回日期:2009-10-21 发布日期:2009-12-15
  • 通讯作者: 李正名 E-mail:nkzml@vip.163.com;nkzml@finechembio.cn
  • 基金资助:

    天津市自然科学基金重点项目

Regioselectivite Synthesis, Structure and Biological Activity of Novel 2,3-Dihydro-2-substitutionalsulfonylhydrazono-3-per-O-acetylglycosyl Thiazoles

WANG Hao-An, LI Yu-Xin, LI Yi-Ming, WANG Su-Hua, LI Zheng-Ming   

  1. (State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2009-08-10 Revised:2009-10-21 Published:2009-12-15

PDF

1236

被引次数

6 | 1

以取代磺酰肼和糖基异硫氰酸酯反应, 生成8种1-取代磺酰基-4-全乙酰糖基氨基硫脲, 然后在ClCH2CHO/CH3COONa/DMF条件下关环, 区域选择性地合成了一系列新型2-取代磺酰基亚肼基-3-全乙酰糖基-2,3-二氢噻唑. 化合物3e的1H-13C HMBC谱图表明1-取代磺酰基-4-全乙酰糖基氨基硫脲与氯乙醛的缩合反应关环位置为氨基硫脲的N-4, 而非N-2. 所有新化合物的结构均经过1H NMR, 13C NMR和元素分析确证, 生物活性初步测定结果表明该类二氢噻唑化合物具有一定的除草活性.

关键词: 1H-13C HMBC相关谱图, 区域选择性, 二氢噻唑

A series of novel 2,3-dihydro-2-phenylsulfonylhydrazono-3-per-O-acetylglycosyl thiazoles were designed and synthesized via reaction of the chloroacetaldehyde with 1-arylsulfonyl-4-per-O-acetylglyco- sylthiosemicarbazides, which were synthesized via condensation of per-O-acetylglycosthiocyanate with substituted phenylsulfonylhydrazines. Their chemical structures were characterized by 1H NMR, 13C NMR and elemental analysis. 1H-13C HMBC of compound 3e revealed the exclusive regioselectivity of these ring closures toward the N-4 position of the thiosemicarbazide moiety. The bioassaay data indicated that this type of novel compounds showed some herbicidal activity.

Key words: 1H-13C HMBC correlation spectra, regioselectivity, 2,3-dihydrothiazoles