摘要/Abstract

1,2,4-三氮唑作为一种含氮五元杂环类化合物, 不仅具有抗炎、抗菌等生物活性, 还是一种重要的有机合成中间体, 对该类化合物进行合成研究具有重要意义. 以廉价易得的胺和醛芳基腙为原料, 在电催化条件下, 利用电化学脱氢[3+2]环化反应, 一步合成了系列取代的1,2,4-三氮唑衍生物, 其结构经¹H NMR、¹³C NMR和HRMS确证. 该反应条件温和, 原子经济性高, 底物范围广, 避免了氧化剂、过渡金属催化剂、酸和碱的使用, 为构建1,2,4-三氮唑骨架提供了一种绿色、可持续的合成途径.
关键词: 1,2,4-三氮唑, [3+2]环化反应, 电化学合成, 绿色化学
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.


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