Easy Access to Fused Tricyclic Quinoline Derivatives through Metal-Free Electrocatalytic [4 + 2] Annulation

IF 3.3 Q2 CHEMISTRY, MULTIDISCIPLINARY ACS Organic & Inorganic Au Pub Date : 2024-08-08 DOI:10.1021/acsorginorgau.4c0003710.1021/acsorginorgau.4c00037
Sayan Ghosh, Samrat Mallick, Devika Karolly and Suman De Sarkar*, 
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Abstract

An efficient electrocatalytic cycloaddition approach for the construction of a lactone- or lactam-fused quinoline framework is documented. Diverse arrays of functionalities are well-compatible under this metal-free, mild, and scalable electro-redox protocol. Mechanistic studies indicate an iodide-mediated electro-oxidation of secondary amines to their corresponding imines and consequent [4 + 2] cycloaddition, fabricating C–C bonds followed by rapid aromatization leading to the six-membered core structure.

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通过无金属电催化 [4 + 2] 嵌合法轻松获得融合三环喹啉衍生物
本文介绍了一种构建内酯或内酰胺融合喹啉框架的高效电催化环化方法。在这种无金属、温和且可扩展的电氧化还原方案下,各种功能阵列都能很好地兼容。机理研究表明,碘化物介导的电氧化反应可将仲胺转化为相应的亚胺,并随之发生 [4 + 2] 环加成反应,生成 C-C 键,然后迅速芳香化,形成六元核心结构。
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来源期刊
ACS Organic & Inorganic Au
ACS Organic & Inorganic Au 有机化学、无机化学-
CiteScore
4.10
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0.00%
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0
期刊介绍: ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.
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