碘催化色酮与吡啶乙酸乙酯[3+2]环化合成结构新颖的中氮茚类化合物  

Iodine-catalyzed [3+2] cyclization for the synthesis of structurally novel indolizines with chromones and 2-pyridylacetates

作　　者：董凯凯 黄强 易东 姬建新[1] 付强 DONG Kaikai;HUANG Qiang;YI Dong;JI Jianxin;FU Qiang(Chengdu Institute of Biology,Chinese Academy of Sciences,Chengdu,Sichuan,610041 P.R.China;University of Chinese Academy of Sciences,Beijing,100049 P.R.China;School of Pharmacy,Southwest Medical University,Luzhou,Sichuan,646000 P.R.China)

机构地区：[1]中国科学院成都生物研究所,四川成都610041 [2]中国科学院大学,北京100049 [3]西南医科大学药学院,四川泸州646000

出　　处：《华西药学杂志》2020年第1期16-23,共8页West China Journal of Pharmaceutical Sciences

摘　　要：目的建立简单、绿色、高效合成结构新颖的中氮茚类化合物的方法。方法以色酮和吡啶乙酸乙酯为底物、1,4-二氯苯为溶剂、二叔丁基过氧化物为氧化剂,在单质碘的催化下,制备中氮茚类化合物。结果与讨论发展了一种操作简单、绿色的方法,合成了一系列结构新颖的中氮茚类化合物,产物结构经1HNMR、13CNMR、19FNMR和HR-MS表征。该反应具有底物适用范围广、收率高和条件温和的优点。初步的机理研究表明反应产生了自由基中间体。OBJECTIVE To develop a simple,green and efficient protocol for the synthesis of structurally novel substituted indolizines.METHODS The corresponding indolizines were synthesized by the reaction of 2-pyridylacetates with chromones in p-dichlorobenzene under air using iodine as catalyst and DTBP as oxidant.RESULTS and CONCLUSION An operationally simple and environmentally friendly method was developed for the synthesis of a wide range of structurally novel substituted indolizines from 2-pyridylacetates and chromones.The structures of the products were characterized by 1HNMR,13CNMR 19FNMR and HR-MS.The reaction features a wide range of substrate scope,high yields and mild conditions.Preliminary mechanistic studies indicated that radical intermediates were involved in the reaction.

关 键 词：中氮茚 环加成 色酮 吡啶乙酸乙酯 单质碘 合成 结构新颖 自由基反应 

分 类 号：R914[医药卫生—药物化学]