Synthesis of Antimicrobial Active 9,10-Phenanthrenequinones by Carbene Organocatalytic Tandem Reactions

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC
Yaoluo Hu, Ya Hong, Yuting Zheng, Yi Huang, Jixiang Chen, Xingxing Wu
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引用次数: 0

Abstract

Phenanthrenequinones (PQs) are extensively studied in synthetic chemistry and materials science, exhibiting noteworthy biological activities essential for drug discovery. The development of efficient synthetic methods for PQ preparation has thus garnered significant attention, particularly through metal-catalyzed transformations. In this study, we present an N-heterocyclic carbene organocatalytic approach that enables the rapid construction of a diverse range of PQs and their derivatives without the need for stoichiometric oxidants or metal mediators. Mechanistically, the initial carbene-catalyzed formation of a benzoin adduct between the aldehyde and ester is critical in initiating a subsequent annulation reaction involving an aryl radical species. Our method represents the first example on the direct construction of PQ frameworks from simple starting materials by means of small-molecule catalysts. Furthermore, the catalytically obtained PQ products exhibit notable antimicrobial activity against common plant pathogens, offering promising potential for agrochemical development.
用卡宾有机催化串联反应合成具有抗菌活性的9,10-菲醌
菲三醌类化合物在合成化学和材料科学中被广泛研究,在药物发现中具有重要的生物活性。因此,PQ制备的高效合成方法的发展引起了极大的关注,特别是通过金属催化转化。在这项研究中,我们提出了一种n -杂环碳的有机催化方法,可以快速构建各种pq及其衍生物,而不需要化学计量氧化剂或金属介质。从机理上讲,在醛和酯之间,最初的由二氧化碳催化形成的苯并苯甲酸合合物对于引发随后的涉及芳基自由基的环化反应至关重要。我们的方法是利用小分子催化剂从简单的起始材料直接构建PQ框架的第一个例子。此外,催化得到的PQ产品对常见植物病原体具有显著的抗菌活性,具有广阔的农化开发潜力。
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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