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探索2-炔基芳基/苄基叠氮化物的性能:吲哚、喹啉及其衍生物的合成方法——过渡金属催化

Exploring the capabilities of 2-alkynyl aryl/benzyl azides: synthesis approaches for indoles, quinolines, and their derivatives transition metal catalysis.

作者信息

Hosseininezhad Seyedmohammad, Pirani Ahmad Abad Sina, Ramazani Ali

机构信息

The Organic Chemistry Research Laboratory (OCRL), Department of Chemistry, Faculty of Science, University of Zanjan Zanjan 45371-38791 Iran

The Convergent Sciences & Technologies Laboratory (CSTL), Research Institute of Modern Biological Techniques (RIMBT), University of Zanjan Zanjan 45371-38791 Iran.

出版信息

RSC Adv. 2025 Jan 14;15(2):1163-1204. doi: 10.1039/d4ra08280j. eCollection 2025 Jan 9.

DOI:10.1039/d4ra08280j
PMID:39811016
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11729253/
Abstract

In recent research, quinoline and indole structures have gained recognition for their significant clinical relevance and effectiveness. These compounds are known for their wide-ranging pharmacological effects, which include anticancer, antibacterial, antifungal, antiviral, and anti-inflammatory properties. Researchers have successfully implemented a variety of innovative synthetic strategies, leading to the creation of numerous compounds that display fascinating biological activities in diverse fields. This has sparked growing interest in developing quinoline and indole-based analogues, given their impressive variety of biological effects. Over the past few years, new, efficient, and more accessible synthetic techniques-such as green chemistry and microwave-assisted synthesis-have been introduced to produce a diverse array of quinoline and indole structures. This development reflects an expanding area of interest in both academic and industrial settings, making it easier to investigate their biological capabilities. In this review, we examine the intriguing transformations of 2-alkynyl aryl and benzyl azide derivatives into indoles and quinolines, emphasizing the role of metal catalysts such as Au, Cu, Rh, Pd, and Ag, from 2011 to 2024. We showcase the variety of substrates involved, highlight notable advancements in this area of research, and address the limitations faced by chemists. Additionally, we offer insights into the mechanisms driving these important reactions, aiming to enhance understanding and inspire future work in this dynamic field.

摘要

在最近的研究中,喹啉和吲哚结构因其显著的临床相关性和有效性而受到认可。这些化合物以其广泛的药理作用而闻名,包括抗癌、抗菌、抗真菌、抗病毒和抗炎特性。研究人员成功实施了各种创新的合成策略,从而创造出许多在不同领域展现出迷人生物活性的化合物。鉴于喹啉和吲哚类化合物令人印象深刻的多种生物效应,这引发了人们对开发基于它们的类似物的兴趣日益浓厚。在过去几年中,已经引入了新的、高效且更易获得的合成技术,如绿色化学和微波辅助合成,以制备各种各样的喹啉和吲哚结构。这一进展反映出学术和工业领域中一个不断扩大的感兴趣领域,使得研究它们的生物学能力变得更加容易。在本综述中,我们考察了2-炔基芳基和苄基叠氮衍生物向吲哚和喹啉的有趣转化,重点强调了2011年至2024年期间金、铜、铑、钯和银等金属催化剂的作用。我们展示了所涉及的各种底物,突出了该研究领域的显著进展,并探讨了化学家所面临的局限性。此外,我们还对驱动这些重要反应的机制提供了见解,旨在增进理解并激发这一充满活力领域的未来研究工作。

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