超声波辅助下离子液体[DDPA][HSO_4]催化Paal-Knorr反应合成吡咯衍生物  

Ultrasonic-assisted paal-Knorr reaction for the synthesis of pyrrole derivatives catalyzed by ionic liquid [DDPA][HSO_4]

作　　者：胡玉林[1,2] 陆明[2] 刘小兵[3] 

机构地区：[1]滁州学院材料与化学工程学院,安徽滁州239000 [2]南京理工大学化工学院,南京210094 [3]井冈山大学化学化工学院,江西吉安343009

出　　处：《河南理工大学学报（自然科学版）》2013年第4期507-512,共6页Journal of Henan Polytechnic University（Natural Science）

基　　金：国家重点基础研究发展计划项目(973项目;613740101);NSFC-NSAF项目(11076017)

摘　　要：研究了一种有效的离子液体[DDPA][HSO4]催化Paal-Knorr反应体系,该体系能够有效地将一系列胺类化合物与2,5—己二酮反应转化为相应的吡咯化合物,产品收率都在80%以上.在超声波辐射下,[DDPA][HSO4]能较好地催化胺与2,5—己二酮反应,当胺用量为10mmol,2,5—己二酮用量为10 mmol,[DDPA][HSO4]用量为1 mmol,甲醇用量为10 mL时,收率可达81%～97%.催化剂可以方便地回收循环使用,[DDPA][HSO4]重复使用5次而催化活性基本保持不变.超声波辐射使得反应时间大大缩短(如苯胺与2,5—己二酮的反应时间由40 min缩短为5 min),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 pyrrole derivatives by Paal-Knorr condensation reaction catalyzed by ionic liquid [DDPA][HSO 4 ]has been investigated and described.The treatment of a series of amines with 2,5hexanedione in the presence of a catalytic amount of [DDPA][HSO 4 ]under ultrasonic radiation conditions gives the corresponding pyrrole derivatives in good to high yields,and all the yields were above 80%.Furthermore,corresponding pyrrole derivatives with 81% ～ 97% yields were synthesized via ultrasonic-assisted PaalKnorr condensation of amine and 2,5-hexanedione using [DDPA][HSO4]as catalyst when the reactions were carried out using amine（10 mmol）,acetonylacetone（10 mmol）,and [DDPA][HSO4 ]（1 mmol） in CH 3 OH（10 mL） at 25 °C.The ionic liquid could be easily recycled and reused without obviously decreasing the catalytic activity.The reaction time of aniline and 2,5-hexanedione was shortened from 40 min to 5 min.Mild reaction conditions,high yields,ease of workup,easy isolation of the compounds,and excellent recyclability of the catalyst are the attractive features of this methodology,which is a good example of green method,and this method has shown good prospects in industrial applications.

关 键 词：Paal-Knorr反应 吡咯衍生物 离子液体 超声波 

分 类 号：O621.3[理学—有机化学]