对甲苯磺酸控制的β-咔啉衍生物微波辅助合成  

Microwave Assisted Synthesis of β-Carboline Derivatives Controlled by p-Toluenesulfonic Acid

作　　者：付玉轩 胡珊珊 郭利杰[1] 李小娟[1] FU Yu-xuan;HU Shanshan;GUO Li-jie;LI Xiao-juan(College of Chemistry and Chemical Engineering,Xinjiang Normal University,Urumqi 830054,China)

机构地区：[1]新疆师范大学化学化工学院,新疆乌鲁木齐830054

出　　处：《化学试剂》2019年第4期425-429,共5页Chemical Reagents

基　　金：新疆维吾尔自治区自然科学基金资助项目(2015211B023)

摘　　要：采用对甲苯磺酸(Ts OH)作为添加剂,在微波反应器中使色氨酸与醛类5 min内完全转化为相应的1-取代-四氢-β-咔啉衍生物。实验表明:在色氨酸与脂肪族醛或芳香族醛发生反应的过程中,质子酸作为添加剂起到了关键性作用。当该反应采用Ts OH作为添加剂时,脂肪族醛与色氨酸反应得到了较好的结果,反应生成的1-取代-四氢-β-咔啉衍生物产率高达95%。1-取代-四氢-β-咔啉衍生物作为合成β-咔啉衍生物的关键中间体,其可在MnO2或酸性K2Cr2O7的氧化作用下合成β-咔啉衍生物。p-Toluenesulfonic acid (TsOH) was used as an additive to completely convert tryptophan and aldehydes into corresponding 1-substituted-tetrahydro-β-caroline derivatives in 5 min in a microwave reactor.Experiments showed that protonic acid played a key role in the reaction of tryptophan with aliphatic aldehydes or aromatic aldehydes.When TsOH was used as an additive in the reaction,the reaction of aliphatic aldehydes with tryptophan gave better results.1-Substituted-tetrahydro-β-caroline derivatives were produced with yields up to 95% by the reaction of aliphatic aldehydes with tryptophan.The 1-substituted-tetrahydro-β- carbaline derivatives were employed as the key intermediate for the synthesis of β-carbaline derivatives,which can be synthesized β-carboline derivatives under the oxidation of MnO2 or acidic K2Cr2O7.

关 键 词：四氢-β-咔啉 β-咔啉衍生物 微波辅助合成 

分 类 号：O626[理学—有机化学]