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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (10): 1888-1893.DOI: 10.6023/cjoc1202201 上一篇    下一篇

研究论文

含1,2,4-三唑和1,3,4-噁二唑硫醚类化合物的合成及结构表征

王海卫, 朱文娟, 于知冉, 李静, 董保东, 廖新成   

  1. 郑州大学化学与分子工程学院 郑州 450052
  • 收稿日期:2012-02-20 修回日期:2012-05-29 发布日期:2012-06-12
  • 通讯作者: 廖新成 E-mail:lxc66@zzu.edu.cn; whw156@163.com
  • 基金资助:

    国家自然科学基金(No. 21171149)资助项目.

Synthesis and Structure Characterization of Sulfur Ethers Containing 1,2,4-Triazole and 1,3,4-Oxadiazole

Wang Haiwei, Zhu Wenjuan, Yu Zhiran, Li Jing, Dong Baodong, Liao Xincheng   

  1. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052
  • Received:2012-02-20 Revised:2012-05-29 Published:2012-06-12
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21171149).

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3

在KOH溶液中, 芳甲酰肼(2)与CS2生成钾盐3; 然后3在水合肼作用下经过环化、取代、肼解得3-巯基-4-氨 基-5-苯基-4H-1,2,4-三唑-乙酸酰肼(6), 6再与CS2回流成环生成化合物5-(4-氨基-5-苯基-4H-1,2,4-三唑-3-硫烷基)-1,3,4-噁二唑-2-硫醇(7), 最后7与取代苄基氯反应得目标化合物A1～A6, 与芳基甲醛反应得终产物B1～B15. 目标化合物的结构均经1H NMR, 13C NMR, IR, MS或HRMS确证结构.

关键词: 1,2,4-三唑, 1,3,4-噁二唑, 硫醚

Compound 3 was prepared by reaction of benzohydrazide (2) with CS2 in the presence of KOH as solvent. This compound converted to (4-amino-5-phenyl-4H-1,2,4-triazol-3-ylsulfanyl)-acetic acid hydrazide (6) by the reactions of cyclization, substitution and hydrazinolysis in the presence of hydrazine hydrate. Then 5-(4-amino-5-phenyl-4H-1,2,4-triazol- 3-ylsulfanylmethyl)-1,3,4-oxadiazole-2-thiol (7) were obtained by a refluence of compound 6 with CS2. This intermediate reacted with several substituted-benzyl chloride to afford a series of new derivatives A1～A6; in the meantime, reacted with several substituted-benzaldehyde to afford a series of new derivatives B1～B15. The structures of new products were characterized by means of 1H NMR, 13C NMR, IR, MS or HRMS techniques.

Key words: 1,2,4-triazole, 1,3,4-oxadiazole, sulfur ether