可见光介导下有机光敏剂诱导三氮唑化合物的合成

The synthesis of triazole compounds via visible light-mediated organic photosensitizer catalysis

光诱导反应与有机金属催化、小分子催化和不对称催化等反应实现了许多结构复杂的杂环化合物和天然有机化合物的合成,丰富和发展了有机反应方法学的研究内容。在众多的杂环化合物中,三氮唑是一类重要的具有生物和药理活性的五元杂环化合物,被广泛应用于医药、农药以及其他精细化工领域。基于此,该研究以取代的叠氮和苯甲酰乙腈作为原料、芘作为有机光催化剂,在可见光介导下,通过[3+2]环加成合成一系列1,4,5-取代的1,2,3-三氮唑化合物,并以核磁氢谱、碳谱、高分辨质谱和熔点等数据对相应目标化合物进行了表征。实验结果表明:该反应条件温和、区域选择性高、官能团兼容性好,反应操作简单,产率高达99%。反应机理揭示了该光照转化的可能反应历程。该研究为1,2,3-三氮唑衍生物的合成提供了一种简单、高效、绿色的方法,同时,丰富了三氮唑杂环化合物的分子库。

Photoinduced reactions,combined with organometallic catalysis,small molecule catalysis,and asymmetric catalysis,have achieved many structurally complex heterocyclic compounds and natural organic compounds,enriching,and developing the research content of organic reaction methodology.Among numerous heterocyclic compounds,triazole is an important class of five membered heterocyclic compounds with biological and pharmacological activities,widely used in pharmaceuticals,pesticides,and other fine chemical fields.Based on this,this study synthesized a series of 1,4,5-substituted 1,2,3-triazole compounds by[3+2]cycloaddition under visible light mediation,using azide and benzoylacetonitrile as raw materials and pyrene as organic photocatalysts,and the corresponding target compounds were characterized using data such as nuclear magnetic resonance H-spectroscopy,C-spectroscopy,high-resolution mass spectrometry and melting point.The experimental results show that the reaction conditions are mild,the regioselectivity is high and the functional group compatibility is good.In addition,the reaction operation is simple,the yield is as high as 99%,and the reaction mechanism reveals the potential reaction course of this photoconversion.This study provides a simple,efficient,and green method for the synthesis of 1,2,3-triazole derivatives,simultaneously enriching the molecular library of triazole heterocyclic compounds.