中断Ugi三组分反应合成异喹啉/喹啉/羰基取代甲胺衍生物

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-17 DOI:10.1021/acs.joc.5c01763

Lei Wang,Yangkai Wang,Xianxiu Xu,Guodong Wang,Shaoguang Sun,Mengying Jia

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引用次数: 0

摘要

采用六氟异丙醇（HFIP）催化的富电子芳基、烯基或杂芳基系结异氰酸酯、醛和胺的Ugi三组分反应，可快速合成各种异喹啉/喹啉/羰基取代甲胺和α-氨基酸衍生物。在这个反应中，原位形成的腈被拴在异氰酸酯上的亲核试剂在分子内捕获，形成相应的杂环框架，其中观察到明显的宝石-二取代基（索普-英戈尔德）效应。

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Synthesis of Isoquinoline/Quinoline/Carboline-Substituted Methylamine Derivatives by an Interrupted Ugi Three-Component Reaction.

A hexafluoroisopropanol (HFIP)-promoted Ugi three-component reaction of electron rich aryl, alkenyl or heteroaryl group-tethered isocyanides, aldehydes and amines was developed for the rapid and general synthesis of a wide range of isoquino-line/quinoline/carboline-substituted methylamine and α-amino acid derivatives. In this reaction, the in situ formed nitrilium was intramolecularly trapped by the nucleophiles tethered at isocyanides to form the corresponding heterocyclic framework, wherein an obviously gem-disubstituent (Thorpe-Ingold) effect was observed.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.