三氟甲磺酸催化的芳基甲基酮与烯酰胺的反应：1-氨基-1-茚和2,4-二烯酰胺的合成
TfOH-Catalyzed Reactions of Aryl Methyl Ketones with Ynamides: Synthesis of 1-Amino-1-indenes and 2,4-Dienamides.
作者信息
Ding Lixia, Wang Nanfang, Qi Chaofan, Chen Jinyue, Chang Junbiao, Wang Xiao-Na
机构信息
Pingyuan Laboratory, State Key Laboratory of Antiviral Drugs, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, P. R. China.
出版信息
J Org Chem. 2024 Sep 20;89(18):13511-13517. doi: 10.1021/acs.joc.4c01712. Epub 2024 Aug 28.
The efficient synthesis of 1-amino-1-indenes and 2,4-dienamides was realized via TfOH-catalyzed reactions of aryl methyl ketones with terminal ynamides in two distinct pathways. Aromatic ketones with high electrophilicity underwent [3 + 2] annulation with ynamides to produce 1-amino-1-indenes, while aromatic ketones with low electrophilicity proceeded under the same conditions to afford 2,4-dienamides. Furthermore, the obtained 1-amino-1-indenes could be converted into the corresponding 1-indenes and dihydro-1-indenes in excellent yields.
通过三氟甲磺酸（TfOH）催化芳基甲基酮与末端烯炔酰胺的反应，以两种不同途径实现了1-氨基-1-茚和2,4-二烯酰胺的高效合成。具有高亲电性的芳香酮与烯炔酰胺发生[3 + 2]环化反应生成1-氨基-1-茚，而具有低亲电性的芳香酮在相同条件下反应得到2,4-二烯酰胺。此外，所得到的1-氨基-1-茚可以以优异的产率转化为相应的茚和二氢茚。
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