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钯催化喹诺酮类化合物的合成与转化。

Palladium-Catalysed Synthesis and Transformation of Quinolones.

机构信息

Department of Chemistry QOPNA and LAQV-REQUIMTE, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal.

出版信息

Molecules. 2019 Jan 9;24(2):228. doi: 10.3390/molecules24020228.

Abstract

Palladium-catalysed reactions have had a large impact on synthetic organic chemistry and have found many applications in target-oriented synthesis. Their widespread use in organic synthesis is due to the mild conditions associated with the reactions together with their tolerance of a wide range of functional groups. Moreover, these types of reactions allow the rapid construction of complex molecules through multiple bond-forming reactions in a single step, the so-called tandem processes. Pd-catalysed reactions have been applied to the synthesis of a large number of natural products and bioactive compounds, some of them of complex molecular structures. This review article aims to present an overview of the most important Pd-catalysed reactions employed in the synthesis and transformations of quinolin-2(1)-ones and quinolin-4(1)-ones. These compounds are widely recognized by their diverse bioactivity, being privileged structures in medicinal chemistry and useful structural moieties for the development of new drug candidates. Furthermore, they hold significant interest due to their host⁻guest chemistry; applications in chemical, biochemical and environmental analyses and use in the development of new synthetic methods. In some cases, the quinolone formation step cannot be ascribed to a claimed Pd-catalysed reaction but this reaction is crucial to get the appropriate substrate for cyclization into the quinolone. Herein we present and discuss different economical, efficient and selective synthetic strategies to access quinolone-type compounds.

摘要

钯催化反应对合成有机化学产生了重大影响,并在目标导向合成中找到了许多应用。它们在有机合成中的广泛应用是由于与反应相关的温和条件以及它们对广泛的官能团的耐受性。此外,这些类型的反应允许通过在单个步骤中进行多次键形成反应来快速构建复杂分子,即所谓的串联过程。钯催化反应已应用于许多天然产物和生物活性化合物的合成,其中一些具有复杂的分子结构。本文旨在综述在喹啉-2(1)-酮和喹啉-4(1)-酮的合成和转化中应用的最重要的钯催化反应。这些化合物因其广泛的生物活性而受到广泛认可,它们是药物化学中的优势结构,也是开发新候选药物的有用结构部分。此外,由于它们的主客体化学,它们具有重要的意义;在化学、生化和环境分析中的应用以及在新合成方法的开发中的应用。在某些情况下,喹啉形成步骤不能归因于声称的钯催化反应,但该反应对于获得适合环化形成喹啉的适当底物至关重要。本文提出并讨论了不同经济、高效和选择性的合成策略,以获得喹啉类化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e76/6359680/40496eb96a45/molecules-24-00228-g001.jpg

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