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Isothiourea-catalyzed addition of aryl acetates to vinylogous imine intermediates generated in situ from arylsulfonyl indoles 异硫脲催化芳基乙酸酯加成到芳基磺酰吲哚原位生成的乙烯基亚胺中间体
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-10 DOI: 10.1016/j.tetlet.2025.155896
Ying Xie , Lixu You , Yi Liu , Yinlong Lai
Indole propionates are essential precursors for the construction of indole-propionic acid with TRPC6 inhibitory activity. Herein, we developed a novel approach to multisubstituted indole propionates via isothiourea-catalyzed addition of aryl acetates to vinylimine intermediates, which are generated in situ from arylsulfonyl indoles under mild conditions. This new method features a broad substrate scope and good yields. Importantly, it enabled us to complete the concise syntheses of indole-propionic acid with TRPC6 inhibitory activity through the hydrolysis of indole propionate.
吲哚丙酸酯是构建具有TRPC6抑制活性的吲哚-丙酸的必要前体。在此,我们开发了一种新的方法,通过异硫脲催化芳基乙酸酯在乙烯胺中间体上加成,在温和的条件下由芳基磺酰基吲哚原位生成多取代吲哚丙酸酯。这种新方法具有衬底范围广、收率高的特点。重要的是,它使我们通过水解吲哚丙酸酯,完成了具有TRPC6抑制活性的吲哚-丙酸的简明合成。
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引用次数: 0
Photoinduced arylation of 3-acyl-substituted indoles with diaryliodonium triflates enabled by electron donor − acceptor complexes 电子供体-受体配合物使3-酰基取代吲哚与三氟酸二芳基碘鎓的光诱导芳基化
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-08 DOI: 10.1016/j.tetlet.2025.155892
Yu-Tao Sun , Jing-Yao Zhou , Dong-En Wu , Mei Hong , Liang Wang
Enabled by the formation of electron donor−acceptor complexes, a photoinduced arylation of 3-acyl-substituted indoles using diaryliodonium triflate as the arylation reagent has been disclosed. No photocatalyst, oxidant or base are required for this transformation. The direct irradiation of the mixture of 3-acyl-substituted indoles and diaryliodonium triflates under visible light in acetonitrile afforded 2-aryl indoles in moderate to good yields.
通过形成电子供体-受体配合物,公开了以三酸二芳基碘鎓为芳基化试剂的3-酰基取代吲哚的光诱导芳基化。这种转化不需要光催化剂、氧化剂或碱。将3-酰基取代吲哚和三氟二芳基碘鎓的混合物在可见光下直接照射于乙腈中,可获得中高收率的2-芳基吲哚。
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引用次数: 0
Revisit the progress in the Ugi reaction: notable advances in synthesis and applications 回顾Ugi反应的进展:合成和应用方面的重大进展
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-08 DOI: 10.1016/j.tetlet.2025.155893
Suchandra Bhattacharjee, Sushmita Gajurel
The Ugi reaction is one of the prevailing multicomponent reactions (MCR) and has evolved into a vital part of contemporary synthetic chemistry. In recent years, using alternate reagents for the Ugi reaction and developing new catalysts have significantly expanded the substrate scope of this specific reaction. The reactions are increasingly being used in novel ways, particularly in materials science and medicinal chemistry. Therefore, there is a need for a comprehensive review article that helps to summarize the existing research articles, provides a relative analysis, and identifies the research gap. This mini review considers the recent developments in Ugi chemistry, mainly from the period 2020–2025, emphasizing the significant advances in reaction conditions, key innovations in substrate diversity, and their applications in medicinal chemistry, including site-selective protein bioconjugation and drug developments. Great attention is placed on the sustainable synthetic approaches, including the use of nano- and photocatalysts, visible-light-mediated synthesis, and the Ugi products synthesized from plant extracts. The review also highlights the advances in enantioselective Ugi reactions facilitated by chiral catalysts and the development of atropisomeric scaffolds. Besides these, it explores the growing utility of the reaction in constructing complex molecular architectures like heterocycles, spirocycles, peptidomimetics, glycomimetics, and functional polymers. In general, this article presents a detailed and current overview of the changing landscape of the Ugi chemistry and outlines future guidelines for its application in both academic as well as commercial research.
Ugi反应是一种流行的多组分反应(MCR),并已发展成为当代合成化学的重要组成部分。近年来,使用替代试剂进行Ugi反应和开发新的催化剂,大大扩大了该特定反应的底物范围。这些反应越来越多地被用于新的方法,特别是在材料科学和药物化学方面。因此,需要一篇综合性的综述文章,帮助总结现有的研究文章,提供相关的分析,并找出研究差距。这篇小综述考虑了Ugi化学的最新发展,主要从2020-2025年,强调了反应条件的重大进展,底物多样性的关键创新,及其在药物化学中的应用,包括位点选择性蛋白质生物偶联和药物开发。重点关注可持续的合成方法,包括纳米和光催化剂的使用、可见光介导的合成以及从植物提取物中合成Ugi产品。综述了手性催化剂促进Ugi对映选择性反应的研究进展和atroisomer支架的研究进展。除此之外,它还探讨了该反应在构建复杂分子结构方面的日益增长的效用,如杂环、螺旋环、肽模拟物、糖模拟物和功能聚合物。总的来说,本文介绍了Ugi化学变化景观的详细和当前概述,并概述了其在学术和商业研究中的应用的未来指导方针。
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引用次数: 0
Nitro radical addition and cyclization of 1,5-enenitriles for making pyrrolidine-2,4-diones 1,5-烯腈的硝基加成和环化制备吡咯烷-2,4-二酮
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-07 DOI: 10.1016/j.tetlet.2025.155881
Mifei Yu, Wentao Shao, Lingfeng Luo, Yue Zhang, Shenghu Yan, Jia-Yin Wang, Xiaoming Ma
A mild and efficient method for the nitro radical-mediated addition and cyclization of N-tethered 1,5-enenitriles is presented. Utilizing commercially available tert-butyl nitrite (t-BuONO) as a practical nitro radical source, this transformation enables the straightforward synthesis of a diverse range of nitro-substituted pyrrolidine-2,4-dione derivatives. The reaction proceeds under metal-free conditions, exhibits broad substrate scope, and offers operational simplicity, highlighting its potential for rapid access to pharmacologically relevant scaffolds.
提出了一种温和而高效的硝基介导的n -链1,5-烯腈加成和环化方法。利用市售的亚硝基叔丁基(t-BuONO)作为一种实用的硝基源,这种转化可以直接合成各种硝基取代吡咯烷-2,4-二酮衍生物。该反应在无金属条件下进行,具有广泛的底物范围,操作简单,突出了其快速获得药理学相关支架的潜力。
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引用次数: 0
Efficient cyanation of amides and thioamides via difluorocarbene-mediated dehydration and desulfurization 通过二氟烃介导的脱水和脱硫高效氰化酰胺和硫酰胺
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-07 DOI: 10.1016/j.tetlet.2025.155891
Tao Zhao, Zixin Chen, Jinghan Bu, Mengyi Huang, Qiang Yang
A novel method involving difluorocarbene-mediated dehydration and desulfurization-cyanation of amides and thioamides has been developed. This approach facilitates the efficient conversion of diverse substrates—including alkyl, alkenyl, alkynyl, and aryl amides, as well as thioamides, urea, and amino acid derivatives—under transition-metal-free conditions without an inert atmosphere. Notably, this strategy provides a straightforward protocol for the late-stage cyanation modification of pharmaceutical amides and other bioactive molecules. The procedure is operationally simple, and some products require only extraction and purification, eliminating the need for column chromatography.
提出了一种以二氟烃为介质的酰胺和硫酰胺脱水脱硫新方法——氰化法。这种方法促进了各种底物的有效转化,包括烷基、烯基、炔基和芳基酰胺,以及硫酰胺、尿素和氨基酸衍生物,在无过渡金属的条件下,没有惰性气氛。值得注意的是,这种策略为药物酰胺和其他生物活性分子的后期氰化修饰提供了一种直接的方案。该方法操作简单,一些产品只需要提取和纯化,不需要柱层析。
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引用次数: 0
Synthesis of new cluster compounds of triazoles containing perhalogenated azides and mono-, tri-perhalopropargyl cores as cages or hostage 含全卤叠氮化物和单、三全卤丙炔核为笼或人质的三唑簇化合物的合成
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-04 DOI: 10.1016/j.tetlet.2025.155877
Fereshteh Khorasani, Reza Ranjbar-Karimi
Herein, we introduce novel triazole compounds comprising a perhalopyridine (PFP or PCP) core as the host with a perhalogenated azide. The SNAr reactions of pentafluoropyridine at positions 4, 2, 6, and two positions 4, 2 were evaluated. Ultimately, a concise synthetic approach utilizing copper-promoted click chemistry (CuAAC) was employed to prepare a library of structurally diverse mono-, di, and tri-1,4-disubstituted-1,2,3-triazoles moieties of (fluoro-chloro) aryl. The chemical structures of the produced compounds were confirmed using various techniques such as FT-IR and NMR spectroscopy.
本文中,我们引入了一种新型的三唑类化合物,该化合物以过氟吡啶(PFP或PCP)为核心,以过卤化叠氮化物为宿主。评价了五氟吡啶在位置4、2、6和两个位置4、2的SNAr反应。最后,利用铜促进点击化学(CuAAC)的简洁合成方法制备了一个结构多样的(氟氯)芳基单、二和三-1,4-二取代-1,2,3-三唑基团文库。利用FT-IR和NMR等各种技术确认了所生成化合物的化学结构。
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引用次数: 0
Soudanones H and I from a freshwater fungus Hongkongmyces sp. 淡水真菌Hongkongmyces sp.的茄酮H和I。
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-03 DOI: 10.1016/j.tetlet.2025.155874
T'ea P. Cameron , Tamam El-Elimat , Sonja L. Knowles , Huzefa A. Raja , Jacques Fournier , Steven P. Maher , Dennis E. Kyle , Nicholas H. Oberlies
Two new compounds were isolated from a freshwater fungus [Hongkongmyces sp. (strain G892)] by bioactivity-directed fractionation against Plasmodium falciparum. The structures of 1 and 2 were elucidated with the use of HRMS and NMR data, and their absolute configurations were identified by ECD spectroscopy. Compound 1 was evaluated for antiplasmodial activity against P. falciparum and cytotoxicity against human liver cancer cell lines.
从一株淡水真菌[Hongkongmyces sp.(菌株G892)]中分离得到两个抗恶性疟原虫的新化合物。利用HRMS和NMR对其中1和2的结构进行了鉴定,并用ECD谱对其绝对构型进行了鉴定。化合物1对恶性疟原虫的抗疟原虫活性和对人肝癌细胞株的细胞毒性进行了评价。
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引用次数: 0
Metal-free aerobic epoxidation of aromatic olefins using V-70 and pivalaldehyde 用V-70和戊醛进行芳香烯烃无金属有氧环氧化反应
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-02 DOI: 10.1016/j.tetlet.2025.155878
Yamato Kato, Miho Kanoh, Hazuki Itoh, Shiori Itoh, Sakura Tanaka, Takayuki Shioiri, Masato Matsugi
A metal-free aerobic epoxidation of olefins was achieved using V-70 (2,2′-azobis(2,4-dimethyl-4-methoxyvaleronitrile)) as a low-temperature radical initiator in combination with pivalaldehyde as a co-oxidant. The method operates under mild conditions with air as the oxidant, converting a broad range of olefins to epoxides in good to excellent yields. This protocol avoids hazardous peroxides, high-valent metal reagents, and halogenated solvents, offering an environmentally benign and practical approach to olefin epoxidation.
以V-70(2,2′-偶氮(2,4-二甲基-4-甲氧基戊腈))为低温自由基引发剂,戊醛为共氧化剂,实现了烯烃的无金属好氧环氧化反应。该方法在温和的条件下,以空气作为氧化剂,以良好的收率将各种烯烃转化为环氧化物。该方案避免了有害的过氧化物、高价金属试剂和卤化溶剂,为烯烃环氧化提供了一种环保和实用的方法。
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引用次数: 0
Ophiogluconoid A: The first pimarane-type diterpenoid glucoside with immunosuppressive activity from Ophiorrhiza brevidentata 蛇皮葡萄素A:首个从蛇皮根中提取的具有免疫抑制活性的海马烷型二萜糖苷
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-01 DOI: 10.1016/j.tetlet.2025.155880
Jia-Yu Jin , Fan Xu , Chun-Hao Du , Li-Na Zou , Ting Huang , Qin Ma , Ping Zhao , Zheng-Hui Li , Bao-Bao Shi , Ji-Kai Liu
Chemical investigation of the secondary metabolites of the aerial parts of Ophiorrhiza brevidentata H. S. Lo resulted in the isolation of a new pimarane-type diterpenoid glucoside, named ophiogluconoid A (1), along with a known biogenic precursor (2). Their structures were elucidated through extensive spectroscopic analysis. Ophiogluconoid A represents the first diterpenoid isolated from genus Ophiorrhiza. Additionally, it inhibited ConA-induced T cell proliferation (IC50 = 4.3 μM) and LPS-induced B cell proliferation (IC50 = 1.6 μM), demonstrating excellent selectivity indices (SI > 10).
对蛇根地上部次生代谢物的化学研究,分离出一种新的海马兰型二萜糖苷,命名为蛇皮葡聚糖a(1),以及一种已知的生物前体(2)。通过广泛的光谱分析阐明了它们的结构。蛇根素A是首个从蛇根属中分离得到的二萜类化合物。此外,它还能抑制cona诱导的T细胞增殖(IC50 = 4.3 μM)和lps诱导的B细胞增殖(IC50 = 1.6 μM),表现出良好的选择性指数(SI > 10)。
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引用次数: 0
Rh(III)-catalyzed oxidative CH annulation of 3-arylisoquinolin-1-ones with diarylalkynes: Direct access to fused isoquinolinone frameworks Rh(III)催化3-芳基异喹啉-1- 1与二芳基炔的氧化CH环化:直接获得融合异喹啉酮框架
IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2025-11-01 DOI: 10.1016/j.tetlet.2025.155871
S. Karthik , C. Sandhya , Ch. Ajay , B. Sridhar , B.V. Subba Reddy
A highly efficient Rh(III)-catalyzed oxidative CH annulation of 3-arylisoquinolin-1-ones with diarylacetylenes has been developed for the synthesis of structurally diverse diaryl-8H-isoquinolino[3,2-a]isoquinolin-8-one scaffolds. This method offers special features such as excellent atom economy, broad substrate scope and high functional group tolerance, offering a valuable synthetic route for accessing polycyclic frameworks. It is a first example on the oxidative annulation of 3-arylisoquinolin-1-ones with alkynes employing a transition metal catalysis.
研究了一种Rh(III)催化的3-芳基异喹啉-1- 1与二芳基乙炔的高效氧化CH环反应,用于合成结构多样的二芳基- 8h -异喹啉-8- 1 [3,2- A]异喹啉-8- 1支架。该方法具有原子经济性好、底物范围广、官能团容忍度高等特点,为获取多环骨架提供了一条有价值的合成途径。这是采用过渡金属催化的3-芳基异喹啉-1- 1与炔的氧化环化的第一个例子。
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引用次数: 0
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Tetrahedron Letters
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