高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (3): 511.doi: 10.7503/cjcu20130698

• 有机化学 • 上一篇    下一篇

含噻二唑基硫脲类化合物的合成

刘汉文(), 裴文丑, 唐子龙, 赵云辉()   

  1. 湖南科技大学化学化工学院, 理论化学与分子模拟省部共建教育部重点实验室, 湘潭 411201
  • 收稿日期:2013-07-22 出版日期:2014-03-10 发布日期:2019-08-01
  • 作者简介:联系人简介: 刘汉文, 男, 教授, 主要从事有机合成研究. E-mail: hwyliu@126.com;赵云辉, 男, 博士, 讲师, 主要从事有机合成与生物医药材料研究. E-mail: 1060126@hnust.edu.cn
  • 基金资助:
    国家科技支撑计划项目子课题(批准号: 2011BAE06B01)和湖南省科学基金(批准号: 11JJ3016)资助

Synthesis of Thioureas Containing Thiadiazole

LIU Hanwen*(), PEI Wenchou, TANG Zilong, ZHAO Yunhui*()   

  1. Key Laboratory of Theoretical Chemistry and Molecular Simulation, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China
  • Received:2013-07-22 Online:2014-03-10 Published:2019-08-01
  • Contact: LIU Hanwen,ZHAO Yunhui E-mail:hwyliu@126.com;1060126@hnust.edu.cn
  • Supported by:
    † Supported by the Sub-project of National Science and Technology Supporting Program of China(No.2011BAE06B01) and the Science Foundation of Hunan Province, China(No.11JJ3016)

摘要:

以噻二唑-2-氨甲基酚(1)为原料, 与异硫氰酸苯酯反应, 以中等到良好的产率得到噻二唑基N-苯基取代硫脲类化合物(3a~3i); 而化合物1与活性较高的N,N-二甲胺基硫代甲酰氯反应, 则可以得到—NH和—OH同时反应的含有N,N-二甲基硫脲和N,N-二甲基硫代氨基甲酸芳酯官能团的产物. 利用核磁共振、 红外光谱以及高分辨质谱等手段对产物结构进行了表征.

关键词: 1,3,4-噻二唑, 硫脲, 异硫氰酸苯酯

Abstract:

Thioureas have been widely applied in pesticides and pharmaceuticals because of their unique biological activities, such as insecticidal, anti-inflammatory, anti-allergic, antiviral, antibacterial, etc. And thiodiazole derivatives usually have anti-allergic, alexipharmic and regulation of plant growth biological activity. The compounds containing thiourea and thiodiazole would provide better biological activities simultaneously according biological activity of the superposition principle. A series of thioureas containing thiodiazole was synthesized from thiodiazole-2-aminomethyl phenols and phenyl isothiocyanate in moderate to good yields. The reaction condition was warm and the scope of substrates was wide. Furthermore, the thiodiazole-2-aminomethyl phenols reacted with a more active reagent dimethylcarbamothioic chloride to afford novel product with thiourea and carbamothioate groups simultaneously. The reactions could afford good results by stirring for 90 min under 60 ℃ and the disubstituted product 5 was the major product. All the new products have the potential applied in pesticides and pharmaceuticals. The structures of the products were characterized by IR, 1H NMR, 13C NMR and HRMS.

Key words: 1,3,4-Thiodiazole, Thiourea, Phenyl isothiocyanate

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