烷基化吡咯并吡咯二酮(DPP)衍生物的合成  

Synthesis of alkylated derivatives of DPP

作　　者：韩亮[1] 王滨[1] 唐梁斌 

机构地区：[1]浙江工业大学化学工程学院,浙江杭州310014

出　　处：《浙江工业大学学报》2015年第4期369-373,共5页Journal of Zhejiang University of Technology

基　　金：国家自然科学基金资助项目(21176223;21406202);浙江省自然科学基金资助项目(13B020012)

摘　　要：以丁二酸二甲酯和对溴苯腈为原料合成对溴苯基取代的DPP衍生物,对其反应条件进行了优化.系统地探究了反应物配比、催化剂和反应时间等因素对反应收率的影响,得到了较优的工艺条件：当投料配比为n（丁二酸二甲酯）∶n（对溴苯腈）=2.4,催化剂叔丁醇钾5当量,叔戊醇中110℃反应5h,收率68.5%.在此基础上以2-噻吩甲腈和丁二酸二甲酯合成了噻吩取代的DPP.进一步对DPP上的N进行烷基化,分别引入甲基、丁基和辛基,合成了五个N-烷基化DPP目标产物.对合成得到的DPP目标产物用核磁氢谱进行了结构鉴定,并测定了紫外吸收光谱和荧光发射光谱.所合成得到的N-烷基化DPP衍生物紫外最大吸收出现在460～550nm之间,荧光发射光谱主要出现在520～560nm之间.p-Bromophenyl substituted DPP derivatives were synthesized with dimethyl succinate and 4-bromobenzonitrile and the reaction conditions were optimized. Through the investigation of the effects of the reactant ratio, catalyst, reaction time on yield, the optimal process conditions were obtained. 4-Bromobenzonitrile reacted with 2.4 equiv, dimethyl succinate in t-amyl alcohol at 110℃ for 5 h in the presence of 5 equivalents of potassium t-butoxide to give the optimal yield 68.5%. Based on the optimal process conditions, thiophene substituted DPP was synthesized with 2-thiophene carbonitrile and dimethyl succinate. Five N-alkylated DPP derivatives were further synthesized with the introduction of methyl, butyl and octyl group. The target products were characterized with1 H NMR and their UV absorption and fluorescence spectra were measured. The UV maximum absorption of N-alkylated DPP derivatives located at 460--550 nm, and the fluorescence emission peaks mainly appeared at 520--560 nm.

关 键 词：吡咯并吡咯二酮 烷基化 合成 紫外光谱 荧光光谱 

分 类 号：O629.113[理学—有机化学]