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通过无金属电催化[4+2]环化反应轻松获得稠合三环喹啉衍生物。

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

作者信息

Ghosh Sayan, Mallick Samrat, Karolly Devika, De Sarkar Suman

机构信息

Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal 741246, India.

出版信息

ACS Org Inorg Au. 2024 Aug 8;4(5):492-497. doi: 10.1021/acsorginorgau.4c00037. eCollection 2024 Oct 2.

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.

摘要

本文报道了一种用于构建内酯或内酰胺稠合喹啉骨架的高效电催化环加成方法。在这种无金属、温和且可扩展的电氧化还原协议下,各种功能基团具有良好的兼容性。机理研究表明,碘介导仲胺电氧化为相应的亚胺,随后发生[4 + 2]环加成,形成碳 - 碳键,接着快速芳构化生成六元核心结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a716/11450728/31959dc21520/gg4c00037_0001.jpg

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