Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (03): 317-323. Previous Articles     Next Articles

Reviews

1-取代-1H-1,2,3-三唑-4-甲酰胺类化合物的设计合成与生物活性

王振军,刘斌,李永红,赵卫光*   

  1. (南开大学元素有机化学国家重点实验室 农药国家工程中心 天津 300071)
  • 收稿日期:2010-07-01 修回日期:2010-09-03 发布日期:2010-10-20
  • 通讯作者: 赵卫光 E-mail:zwg@nankai.edu.cn;zhaowg@syn.nankai.edu.cn;zhaoweiguang@foxmail.com

Synthesis and Bioactivity of Novel 1-Substituted- 1H-1,2,3-triazole-4-carboxamide

WANG Zhen-Jun, LIU Bin, LI Yong-Hong, ZHAO Wei-Guang   

  1. (State Key Laboratory of Elemento-Organic Chemistry, National Pesticide Engineering Research Cen-ter, Nankai University, Tianjin 300071)
  • Received:2010-07-01 Revised:2010-09-03 Published:2010-10-20
  • Contact: ZHAO Wei-Guang E-mail:zwg@nankai.edu.cn;zhaowg@syn.nankai.edu.cn;zhaoweiguang@foxmail.com

1,2,3-Triazole amide derivatives containing triazole as a bioisoster of pyrazole were designed according to “bioisoteric replacement” from pyrazole amide fungicide. Seventeen novel 1-substituted-1H- 1,2,3-triazole-4-carboxamide derivatives were quickly synthesized through the copper(I)-catalyzed Huisgen 1,3-dipolar cycloadditions of organic azide compounds and propiolamide, which was synthesized from propiolic acid. With Cu/C as the catalyst and triethylamine as the additive, the coupling product substituted bis-1,2,3-triazole 17 was obtained in a moderate yield when cyclizing intermediate N-(3,4-dimethoxy- phenethyl)propiolamide (4a) and 2-azido-1,1,1-trifluoroethane (14). The structures of the target compounds were confirmed by 1H NMR spectra, elemental analysis or high resolution mass spectra (HRMS). The investigation of the target compound bioactivities show that, some of them like 6a, 6e, 6k and 6l perform good herbicidal activity at 100 μg/mL, even though they have a poor fungicidal action.

Key words: 1,2,3-triazole, amide, click chemistry, coupling, herbicidal activity