水介质中9,10-二芳基吖啶的洁净合成有机化学.pdfVIP

2009 年第 29 卷 有 机 化 学 Vol. 29, 2009 第 2 期, 239～244 Chinese Journal of Organic Chemistry No. 2, 239～244 ·研究论文· 水介质中 9,10-二芳基吖啶的洁净合成 史达清*,a,b 拾景文b 姚 浩b (a 苏州大学化学化工学院 苏州 215123) (b 徐州师范大学化学化工学院 徐州 221116) 摘要 水介质中在十二烷基磺酸钠(SDS)催化下, 席夫碱与双甲酮反应合成了一系列 9,10-二芳基吖啶衍生物, 同时分 离得到一种中间产物 . 所有产物的结构通过红外光谱和 1H NMR 光谱确定, 产物 10-(4-氯苯基)-9-(4- 甲氧基苯 基)-3,3,6,6- 四甲基-3,4,6,7,9,10-六氢化吖啶-1,8(2H,5H)-二酮(3i)和中间产物 2-{4-氯苯基-[2-(4- 甲氧基苯基氨基)-4,4-二 甲基-6-氧代环已-1-烯基] 甲基}-3-羟基-5,5-二甲基环已-2-烯酮(4h) 的结构还通过单晶 X 射线衍射分析确证. 关键词 9,10-二芳基吖啶; 合成; 水介质; 双甲酮 Clean Synthesis of 9,10-Diarylacridine Derivatives in Aqueous Media Shi, Daqing*,a,b Shi, Jingwenb Yao, Haob a ( College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123) (b College of Chemistry and Chemical Engineering, Xuzhou Normal University , Xuzhou 221116) Abstract 9,10-Diarylacridine derivatives were synthesized by the reaction of Schiff base with dimedone using sodium dodecanesulfonate (SDS) as catalyst in aqueous media. An intermediate was separated. The 1 structures of all the products were determined by IR and H NMR spectra and the structures of product 10-(4-chlorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H ,5H)- dione (3i) and the intermediate 2-{(4-chlorophenyl)[2-(4-methoxyphenylamino)-4,4-dimethyl-6-oxocyclo- hex-1-e