一种四氢苯并吡喃及其衍生物的水相合成  

Synthesis of a tetrahydrobenzo-pyran and its derivatives in aqueous medium

作　　者：高洁[1] 刘硕[2] 周红英 朱婉莉 刘璐[1] 应安国[1,4] 

机构地区：[1]台州学院医药化工学院,浙江台州318000 [2]天津大学化工学院,天津300072 [3]浙江建业化工股份有限公司,浙江杭州311604 [4]台州学院应用化学研究所,浙江台州318000

出　　处：《化学研究》2014年第3期247-253,共7页Chemical Research

基　　金：国家自然科学基金项目(No.21106090);浙江省低碳脂肪胺工程技术研究中心开放基金项目(2012E10033);台州学院校立学生科研项目(13XS26)

摘　　要：制备了一种以三乙烯二胺(DABCO)为基础的离子液体;在水溶剂中,以该离子液体为催化剂催化三组分一锅法制备四氢苯并吡喃的反应,得到2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃;考察了反应时间、催化剂用量、催化剂加入时间、反应温度对反应收率的影响,确定了最优反应条件;由不同的芳香醛和活性亚甲基化合物制备了一系列四氢苯并吡喃衍生物,并讨论了可能的反应机理.结果表明,所选用的合成反应条件温和、时间短、收率高、后处理简单,且催化剂重复使用4次催化效果变化不大;就反应机理而言,所用催化剂具有双重催化活性.1 ,4-diazabicyclo[2 .2 .2]octane （denoted as DABCO） based ionic liquid was synthe-sized .As-obtained DABCO-based ionic liquid was adopted as a catalyst to catalyze the one-pot three-component condensation reaction for synthesizing 4H-benzo[b]pyran derivatives in aque-ous media affording target compound 2-amino-3-cyano-4-aryl-7 ,7-dimethyl-5-oxo-4H-5 ,6 ,7 ,8-tetrahydrobenzo[b]pyran .The effects of reaction time ,catalyst dosage ,catalyst-adding time , and reaction temperature on the yield were investigated ,and the optimal reaction condition was established .Moreover ,various aromatic aldehydes and active methylene compounds were a-dopted as starting materials to synthesize a series of tetrahydrobenzo-pyran compounds ,and possible reaction mechanisms were discussed .Results indicate that as-established synthesis route has the advantages of mild reaction condition ,short reaction time ,high yield and easy post-treatment ,while the catalyst retains nearly unchanged activity after 4 times of recycle .In terms of the reaction mechanisms ,as-prepared DABCO-based ionic liquid catalyst exhibits dual catalytic activity .

关 键 词：三乙烯二胺 离子液体 四氢苯并吡喃 衍生物 水相合成 

分 类 号：O626.31[理学—有机化学]