Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2476-2484.DOI: 10.6023/cjoc202011029 Previous Articles     Next Articles



赵志恒a, 李鸣a, 周娅琴a, 何永辉a, 张丽珠a, 李干鹏a, 谷利军a,b,*()   

  1. a 云南民族大学民族医药学院 民族药资源化学国家民委-教育部重点实验室 昆明 650500
    b 贵州大学 绿色农药和农业生物工程教育部重点实验室 贵阳 550025
  • 收稿日期:2020-11-23 修回日期:2021-01-24 发布日期:2021-02-22
  • 通讯作者: 谷利军
  • 基金资助:
    国家自然科学基金(21662045); 贵州大学绿色农药和农业生物工程教育部重点实验室开放基金(2018GDGP0103)

Synthesis of 1,2,4-Triazoles via the Electrochemical Oxidative [3+2] Annulation

Zhiheng Zhaoa, Ming Lia, Yaqin Zhoua, Yonghui Hea, Lizhu Zhanga, Ganpeng Lia, Lijun Gua,b()   

  1. a Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming 650500
    b Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025
  • Received:2020-11-23 Revised:2021-01-24 Published:2021-02-22
  • Contact: Lijun Gu
  • Supported by:
    National Natural Science Foundation of China(21662045); Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University(2018GDGP0103)

1,2,4-Triazoles, standing for a class of five-membered nitrogenous heterocyclic compounds, show anti-inflam- matory, anti-fungal and other biological activities. They also served as important intermediates in organic synthesis. Thus, the pursuit of general and efficient synthesis of 1,2,4-triazoles that controls the introduction of substituents in a highly regioselective fashion has been of continued interest to synthetic organic chemists. In this paper an electrochemical dehydrogenative [3+2] annulation used for the synthesis of 1,2,4-triazoles from cheap and readily available amines and hydrazones was developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS analyses. Advantageously, this method proceeds in a transition-metal-, acid-, base- and external oxidant-free fashion to provide a variety of functionalized 1,2,4-triazoles. The reaction constitutes a new transformation from hydrazones and amines to 1,2,4-triazoles, providing a unifying, simple and environmentally friendly approach to the currently available methods.

Key words: 1,2,4-triazoles, [3+2] annulation, electrochemical synthesis, green chemistry.