苯并吡喃腈类氰基乙烯化合物的合成研究  

Studies on the Synthesis of Benzopyrannitrile-type Cyanoethylene Compounds

作　　者：曹西颖 黎忠昊 于冉冉 叶蕴仪 谢佳瑜 李煌 汪朝阳[1] CAO Xiying;LI Zhonghao;YU Ranran;YE Yunyi;XIE Jiayu;LI Huang;WANG Zhaoyang(School of Chemistry,South China Normal University,Guangzhou 510006,China)

机构地区：[1]华南师范大学化学学院,广东广州510006

出　　处：《广州化学》2025年第2期7-14,I0001,F0003,共10页Guangzhou Chemistry

基　　金：广东省基础与应用基础研究项目(No.2021A1515012342)。

摘　　要：氰基乙烯类化合物的合成与应用,近年来颇受关注,苯并吡喃腈作为一种与苯环稠合的氰基乙烯类化合物,是有机合成中重要的合成子。以廉价易得的色酮(苯并吡喃酮)类化合物和丙二腈为原料,在醋酸酐和氧化铝的作用下,通过脱水缩合反应合成苯并吡喃腈类化合物,优化了反应条件,考察了底物的适用范围,用1H-NMR、^(13)C-NMR、19F-NMR以及高分辨质谱(HR-MS)对所合成的化合物进行表征分析。结果表明,反应中氧化铝的加入,有利于以高产率得到系列苯并吡喃腈化合物。更重要的是,该方法不止适用于苯并吡喃酮类底物,硫代苯并吡喃酮类底物也同样适用。新的合成研究丰富了氰基乙烯类化合物的多样性,有利于绿色合成化学的发展。The synthesis and application of cyanoethylene compounds have attracted much attention in recent years.Benzopyrannitrile,as a kind of cyanoethylene compound fused with the benzene ring,is an important synthon in organic synthesis.In this paper,15 benzopyrannitrile compounds were synthesized by dehydrating condensation reaction using cheap and readily available chromones(benzopyranones)and malononitrile as raw materials under the action of acetic anhydride and alumina.The reaction conditions were optimized and the scope of application of the substrate was observed.These synthesized compounds were well characterized by 1HNMR,^(13)C-NMR,19F-NMR and high resolution mass spectrometry(HR-MS).The results show that the addition of alumina in the reaction is beneficial to obtain a series of benzopyran nitrile compounds in high yield.More importantly,this method is not only suitable for benzopyranones,but also for thiobenzopyranone substrates.This new synthesis research enriches the diversity of cyanoethylene compounds and is conducive to the development of green synthetic chemistry.

关 键 词：色酮 苯并吡喃腈 氧化铝 脱水缩合反应 氰基乙烯化合物 

分 类 号：O621.3[理学—有机化学]