通过金(I)催化的环异构化和分子内乌尔曼型偶联反应简易合成偶氮菲类生物碱大黄素

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC Journal of Heterocyclic Chemistry Pub Date : 2024-09-02 DOI:10.1002/jhet.4889

Eunyeong Kim, Young Taek Han

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引用次数: 0

摘要

我们实现了一种γ-内酰胺融合氮杂菲生物碱 eupolauramine 的简便高效合成。该合成的主要特征包括金（I）催化的 N-萘基氨基丁酰胺中间体的环异构化和随后的分子内乌尔曼型偶联反应。这项研究清楚地证明了共价金属催化环异构化策略在构建结构复杂的吡啶融合杂环支架方面的实用性。

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Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)-Catalyzed Cycloisomerization and Intramolecular Ullmann-Type Coupling Reaction

A concise and efficient synthesis of the γ-lactam-fused azaphenanthrene alkaloid eupolauramine has been achieved. The key feature of the synthesis involves Au(I)-catalyzed cycloisomerization of N-naphthyl aminobutynamide intermediate and subsequent intramolecular Ullmann-type coupling reaction. This study clearly demonstrated the usefulness of coinage metal-catalyzed cycloisomerization strategy in the construction of architecturally sophisticated pyridine-fused heterocyclic scaffolds.

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来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.