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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (9): 1096-1105. 上一篇    下一篇

研究论文

N-2-多氟烷基乙基取代1,3,4-噁二唑-2-硫酮及1,2,4-三唑-5-硫酮类化合物的合成和密度泛函理论研究

蒋历辉a，李治章b，陈超越c，尹凯a，陈金文a
王小勇b，黄勇a，向建南*,a   

  1. (a湖南大学化学化工学院 长沙 410082)
    (b湖南科技学院化学系 永州 425100)
    (c安徽理工大学化学工程系 淮南 232001)
  • 收稿日期:1900-01-01 修回日期:1900-01-01 发布日期:2007-08-30
  • 通讯作者: 向建南

Synthesis and Density Functional Theory Study of N-2-Perfluoro-alkylethyl-substituted 1,3,4-Oxadiazole-2-thiones and 1,2,4-Triazole-5-thiones

JIANG Li-Huia,LI Zhi-Zhangb,CHEN Chao-Yuec,YIN Kaia,CHEN Jin-Wena
WANG Xiao-Yongb,HUANG Yonga,XIANG Jian-Nan*,a   

  1. (a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
    (b Chemical Department, Hunan University of Science and Engineer-ing, Yongzhou 425100)
    (c Department of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001)
  • Received:1900-01-01 Revised:1900-01-01 Published:2007-08-30
  • Contact: XIANG Jian-Nan

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为改善二唑及三唑类化合物的生物活性, 设计合成了一系列多氟烷基乙基取代的1,3,4-噁二唑-2-硫酮6a～6l及1,2,4-三唑-5-硫酮类化合物9a～9l. 1H NMR, 19F NMR, IR和MS谱以及元素分析表征了它们的结构; 实验结果与Materials Studio 3.0中的Dmol3计算模块理论计算表明了唑环上的NH较之CONH中的NH更易进行烷基化反应.

关键词: 多氟烷基, 密度泛函理论, 1,3,4-噁二唑-2-硫酮, 合成, 1,2,4-三唑-5-硫酮

To improve their bioactivities of oxadiazole and triazole analogues, a series of N-2-perfluoroalkylethyl-substituted 1,3,4-oxadiazole-2-thiones 6a～6l and 1,2,4-triazole-5-thiones 9a～9l were synthesized and their structures were confirmed by 1H NMR, 19F NMR, IR, MS spectra and elemental analysis. The experimental results and the calculation showed that the hydrogen of NH group in heterocycle was more active than the hydrogen on CONH to finish alkyl-substitution reaction on nitrogen through the computing module Dmol3 of Materials Studio 3.0.

Key words: 1,2,4-triazole-5-thione, synthesis, 1,3,4-oxadiazole-2-thione, density functional theory, perfluoroalkyl