2,6-二溴代呋喃基-4-对甲苯基吡啶的合成及性质研究  

Synthesis and Properties of 2,6-Dibromofuranyl-4-p-tolyl Pyridine

作　　者：许佳炫 张贵敏 孙齐艳 毛盼 刘意 Xu Jiaxuan;Zhang Guiming;Sun Qiyan;Mao Pan;Liu Yi(College of Chemistry and Materials Science,Guizhou Education University,Guiyang 550018,China)

机构地区：[1]贵州师范学院化学与材料学院,贵州贵阳550018

出　　处：《云南化工》2023年第9期40-43,共4页Yunnan Chemical Technology

基　　金：贵州师范学院大学生科研项目(2021DXS040)。

摘　　要：以2-乙酰呋喃和对甲基苯甲醛为原料,氨水为氮源,水/乙醇为溶剂,经Krohnke吡啶合成反应制备了2,6-二呋喃基-4-对甲苯基吡啶。以该化合物为原料,N-溴代丁二酰亚胺为溴化剂,THF为溶剂,三氯化铁为催化剂,在无水无氧条件下经亲电取代反应合成了2,6-二溴代呋喃基-4-对甲苯基吡啶。采用核磁共振氢谱、质谱、紫外可见光谱,分析了2,6-二呋喃基-4-对甲苯基吡啶和2,6-二溴代呋喃基-4-对甲苯基吡啶的结构及光谱性质。结构分析表明,溴代可能发生在两个呋喃环的5号位碳原子上。紫外可见吸收光谱分析发现,2,6-二溴代呋喃基-4-对甲苯基吡啶相对于2,6-二呋喃基-4-对甲苯基吡啶红移了9 nm。这表明溴代后,溴和呋喃环发生p-π共轭,化合物能隙降低,最大吸收波长发生红移。2,6-Difuranyl-4-tosylpyridine was prepared by the Krohnke pyridine synthesis reaction using 2-acetylfuran and p-methylbenzaldehyde as raw materials,ammonia as the nitrogen source and water/ethanol as the solvent.Using this compound as raw material,N-bromosuccinimide as brominating agent,THF as solvent and ferric chloride as catalyst,2,6-dibromofuranyl-4-p-tolyl pyridine was synthesized by electrophilic substitution reaction under anhydrous and anaerobic conditions.The structural and spectroscopic properties of 2,6-difuranyl-4-p-tolyl pyridine and 2,6-dibromofuranyl-4-p-tolyl pyridine were analyzed by 1H NMR spectroscopy,mass spectrometry,and UV-visible spectroscopy.The structural analysis results showed that the bromination may occur at the carbon atom in the 5 position of both furan rings.UV-vis absorption spectroscopy revealed that 2,6-dibromofuranyl-4-tosylpyridine was red-shifted by 9 nm compared with 2,6-difuranyl-4-tosylpyridine,which indicated that the p-πconjugation between bromine and furan ring,the reducing energy gap and red-shifting the maximum absorption wavelength occurred after the bromine substitution.

关 键 词：多联吡啶 Krohnke吡啶合成反应 溴代 结构表征 光学性质 

分 类 号：TQ253[化学工程—有机化工]