PEG_(1000)-DIL/甲苯温控两相体系催化四氢-β-咔啉类化合物的合成研究  

Study on the Synthesis of Tetrahydro-β-carb- oline Derivatives in PEG_(1000)-DAIL/toluene Temperature-dependent Biphasic System

作　　者：胡玉林[1] 陆明[2] 方东[1] 

机构地区：[1]盐城师范学院化学化工学院,江苏盐城224002 [2]南京理工大学化工学院,江苏南京210094

出　　处：《盐城工学院学报（自然科学版）》2013年第3期14-19,共6页Journal of Yancheng Institute of Technology:Natural Science Edition

基　　金：国家重点基础研究发展计划项目(973项目;No.613740101);国家自然科学基金委员会-中国工程物理研究院联合基金(NSFC-NSAF项目;No.11076017)

摘　　要：一种有效的离子液体PEG1000-DAIL/甲苯温控两相体系催化Pictet-Spengler反应体系,能够有效的将一系列醛类化合物与色胺反应转化为相应的四氢-β-咔啉类化合物,产品收率都在88％以上.当色胺用量为5 mmol,醛用量为5 mmol,PEG1000-DAIL用量为10 mL,甲苯用量为10 mL时,收率可达88％～93％.催化剂可以方便的回收循环使用,PEG1000-DAIL重复使用5次而催化活性基本保持不变.反应条件温和,收率较高,操作方便,后处理简单,该工艺符合绿色化学的发展方向,具有良好的应用前景.An efficient synthesis of tetrahydro- β -carboline derivatives by Pictet -Spengler condensation reaction catalyzed by PEG1000 - DAIL/toluene temperature - dependent biphasic system has been described. Treatment of a series of aldehydes with tryptamine in the presence of a catalytic amount of PEG1000- DAIL under homogeneous reaction conditions gives the corresponding tetrahydro - β - carboline derivatives in good to high yields, and all the yields were above 88%. Furthermore, corresponding tetrahydro -β- carboline derivatives with 88 ~ 93% yields were synthesized via Pictet - Spengler condensation of aldehydes and tryptamine in PEG1000 - DAIL/toluene temperature - dependent biphasic system when the reactions were carried out using tryptamine （5 retool）, aldehyde （5 mmol）, and PEG1000 -DAIL （0mL） in toluene （10 mL） at 80 ℃. The ionic liquid could be easily recycled and reused without obviously decreasing the catalytic activity. Mild reaction conditions, ease of workup, high yields, stability, easy isolation of the compounds, good thermoregulated biphasic behavior of ionic liquid, and excellent recyclability of the catalyst are the attractive features of this methodology, which is a good example of green condensation method, and this method showed has good prospects in industrial applications.

关 键 词：Pictet-Spengler反应 四氢-β-咔啉类化合物 离子液体 温控两相体系 

分 类 号：O621.3[理学—有机化学]