酸催化的烯丙基苯与四嗪环化反应的研究  

Study on the Acid-Catalyzed Cyclization Reaction of Allylbenzenes and Tetrazine

作　　者：刘文卿 王贺 王欣 李蕾 LIU Wenqing;WANG He;WANG Xin;LI Lei(School of Petrochemical Engineering,Liaoning Petrochemical University,Fushun Liaoning 113001,China)

机构地区：[1]辽宁石油化工大学石油化工学院,辽宁抚顺113001

出　　处：《石油化工高等学校学报》2025年第2期62-71,共10页Journal of Petrochemical Universities

基　　金：辽宁省科技厅面上项目(2022MS361);辽宁省教育厅项目(JYTMS20231451)。

摘　　要：茚并哒嗪衍生物因具有良好的生物活性,在农药和医药等领域具有广泛的应用前景,因此开发一种快速高效的合成方法越来越受到研究者的关注。设计了一种酸催化的烯丙基苯与四嗪官能化环化反应,对反应中间体进行捕获并使用核磁共振波谱仪对中间体以及产物进行了结构表征。结果表明,该反应经历分子间[4+2]环加成和分子内傅克烷基化反应等历程,实现了一步合成茚并哒嗪衍生物;反应还具有广阔的底物范围和良好的官能团相容性,能够以67%~95%的产率得到一系列的茚并哒嗪衍生物;在克级实验研究中,目标产物的产率可以达到81%,证明了该反应具有潜在的应用价值。Indeno[1,2-d]pyridazine derivatives have wide applications in pesticides,pharmaceuticals,and other fields due to their excellent biological activities.Therefore,the development of rapid and efficient synthetic methods for these compounds has attracted increasing attention from researchers.A novel acid-catalyzed cyclization reaction between allylbenzene and tetrazine was designed.Reaction intermediates were trapped,and their structures,along with those of the products,were characterized using nuclear magnetic resonance spectroscopy.The results indicate that the reaction proceeds through intermolecular[4+2]cycloaddition and intramolecular Friedel-Crafts alkylation processes,enabling one-step synthesis of indeno[1,2-d]pyridazine derivatives.The reaction also exhibits a broad substrate scope and good functional group compatibility,yielding a series of indeno[1,2-d]pyridazine derivatives with 67%~95%yields.In gram scale experiments,the target product was obtained with an 81%yield,demonstrating the potential practical value of this reaction.

关 键 词：烯丙基苯 茚并哒嗪衍生物 [4+2]环化反应 傅克反应 

分 类 号：TQ254.1[化学工程—有机化工]