首页|期刊导航|云南民族大学学报(自然科学版)|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

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OACSTPCD

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

中文摘要英文摘要

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 and β-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 deriva-tives 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 hy-drogen 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 deriv-atives.

吴沁;罗焰;万娟;徐卓婷;黄超

云南民族大学 化学与环境学院,云南 昆明 650503

化学

2-硝基查尔酮β-酮酯无过渡金属咔唑类化合物

2-nitrochalconesβ-ketoestermetal-freealkalicarbazole compounds

《云南民族大学学报(自然科学版)》 2024 (005)

582-589 / 8

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.

10.3969/j.issn.1672-8513.2024.05.006

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