Synthesis of Pyrido-[2,1-a]isoquinoline Derivatives via Gold(I)-Catalyzed Intramolecular Cascade Reaction of Enamides,Advanced Synthesis & Catalysis

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Synthesis of Pyrido-[2,1-a]isoquinoline Derivatives via Gold(I)-Catalyzed Intramolecular Cascade Reaction of Enamides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-11-23 , DOI: 10.1002/adsc.202300908
Xin-Ming Xu ₁ , Sen Chen ₁ , Wenzhong Li ₁ , Xuesi Zhang ₁ , Zhongyuan Zhao ₁ , Xinyue Cao ₁ , Yuhang Yao ₁ , Xiangmin Wang ₁ , Zu-Li Wang ₂

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A gold(I)-catalyzed intramolecular cascade reaction of tertiary enamides has been developed, which provides a method for the preparation of diverse pyrido[2,1-a]isoquinoline derivatives with good function group tolerance. Preliminary investigation of the reaction mechanism indicate that this process comprises a nucleophilic addition of the enamide to an alkynyl group, followed by the capture of the acyliminium ion by an electron-rich aromatic component. Additionally, scale-up experiments and further transformations of pyrido-[2,1-a]isoquinolines underscore the utility of this methodology.

中文翻译：

金(I)催化烯酰胺分子内级联反应合成吡啶并-[2,1-a]异喹啉衍生物

开发了金(I)催化的叔烯酰胺分子内级联反应，为制备具有良好官能团耐受性的多种吡啶并[2,1-a]异喹啉衍生物提供了一种方法。反应机理的初步研究表明，该过程包括烯酰胺与炔基的亲核加成，然后由富电子芳香族组分捕获酰亚胺离子。此外，吡啶并-[2,1-a]异喹啉的放大实验和进一步转化强调了该方法的实用性。

更新日期：2023-11-23

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