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通过多相过渡金属催化交叉偶联反应合成含氮杂芳烃的最新进展。

Recent advances in the synthesis of N-containing heteroaromatics via heterogeneously transition metal catalysed cross-coupling reactions.

机构信息

Institut de Recherches sur la Catalyse et l'Environnement de Lyon (IRCELYON), Université de Lyon, CNRS, UMR 5256, 2 Avenue Albert Einstein, Villeurbanne F-69626, France.

出版信息

Molecules. 2011 Jun 23;16(6):5241-67. doi: 10.3390/molecules16065241.

DOI:10.3390/molecules16065241
PMID:21701436
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6264783/
Abstract

N-containing heteroaromatics are important substructures found in numerous natural or synthetic alkaloids. The diversity of the structures encountered, as well as their biological and pharmaceutical relevance, have motivated research aimed at the development of new economical, efficient and selective synthetic strategies to access these compounds. Over more than 100 years of research, this hot topic has resulted in numerous so-called "classical synthetic methods" that have really contributed to this important area. However, when the selective synthesis of highly functional heteroaromatics like indoles, quinolones, indoxyls, etc. is considered these methods remain limited. Recently transition metal-catalysed (TM-catalysed) procedures for the synthesis of such compounds and further transformations, have been developed providing increased tolerance toward functional groups and leading generally to higher reaction yields. Many of these methods have proven to be the most powerful and are currently applied in target- or diversity-oriented syntheses. This review article aims at reporting the recent developments devoted to this important area, focusing on the use of heterogeneous catalysed procedures that include either the formation of the heterocyclic ring towards the nuclei or their transformations to highly substituted compounds.

摘要

含氮杂环芳烃是许多天然或合成生物碱中重要的结构单元。所遇到的结构的多样性,以及它们的生物和药物相关性,促使人们研究开发新的经济、高效和选择性的合成策略来获得这些化合物。在 100 多年的研究中,这个热门话题产生了许多所谓的“经典合成方法”,这些方法确实为这个重要领域做出了贡献。然而,当考虑到高度官能化的杂环芳烃(如吲哚、喹啉、吲哚啉等)的选择性合成时,这些方法仍然存在局限性。最近,用于合成这些化合物和进一步转化的过渡金属催化(TM 催化)方法已经被开发出来,这些方法对官能团的耐受性更高,通常导致更高的反应收率。其中许多方法已被证明是最有效的方法,目前已应用于目标或多样性导向的合成中。本文综述了这一重要领域的最新进展,重点介绍了使用包括杂环环化到核或其转化为高取代化合物的多相催化程序。

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