碱催化2-硝基查尔酮和β-酮酯绿色高效构筑咔唑类衍生物  

Base-catalyzed green and efficient construction of carbazole derivatives from 2-nitrochalcone andβ-keto ester

作　　者：吴沁 罗焰 万娟 徐卓婷 黄超 WU Qin;LUO Yan;WAN Juan;XU Zhuo-ting;HUANG Chao(School of Chemistry and Environment,Yunnan Minzu University,Kunming 650503,China)

机构地区：[1]云南民族大学化学与环境学院,云南昆明650503

出　　处：《云南民族大学学报（自然科学版）》2024年第5期582-589,共8页Journal of Yunnan Minzu University:Natural Sciences Edition

基　　金：国家自然科学基金(21662046,21202142);云南省教育厅科学研究基金(2021Y667);云南民族大学化学与环境学院党员先锋“双创”培育项目立项。

摘　　要：在碱促进和缺乏过渡金属的条件下,以2-硝基查尔酮和β-酮酯类化合物为原料,通过分子内共轭加成选择性形成4个键并活化硝基,最终通过一锅法绿色高效合成了13种咔唑类衍生物,收率在75%~90%之间.该反应首先通过Michael加成得到烯醇化中间体,再与硝基反应形成双环中间体,在碱的诱导下脱去一分子过氧化氢,从而转化为咔唑目标化合物.该方法原料简单易得,绿色高效,操作简单,原子经济性高,对环境友好且收率良好,后处理简单,为合成咔唑类衍生物提供新的策略.Under base-promoted and transition-metal-free conditions,2-nitrochalcone andβ-keto ester compounds serve as raw materials to selectively form four bonds via intramolecular conjugate addition and activation of the nitro group.This approach culminates in a one-pot,green,and efficient synthesis of 13 carbazole derivatives with yields ranging from 75%to 90%.Firstly,the enolization intermediate was obtained by Michael addition,and then reacted with nitro groups to form bicyclic intermediate.Under the induction of alkali,one molecule of hydrogen peroxide is removed,converting to the targetcarbazole compound.This method has the advantages of simple and accessible raw materials,green and high efficiency,simple operation,high atomic economy,environmental friendliness,good yield and simple post-treatment,which provides a new strategy for synthesizing carbazole derivatives.

关 键 词：2-硝基查尔酮 β-酮酯 无过渡金属 碱 咔唑类化合物 

分 类 号：O621.3[理学—有机化学]