Tetrahedron最新文献

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Novel pyridine based 1,3,4-oxadiazole hybrids: Synthesis, biological potential, molecular docking studies and ADMET properties 新型吡啶基1,3,4-恶二唑杂化物：合成、生物学潜力、分子对接研究和ADMET性质

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-01-05 DOI: 10.1016/j.tet.2025.135110

Darshan H. Divetia , Devayat R. Bhadarka , Vijay H. Dodiya , Jainish U. Joshi , Paresh K. Patel , Tushar J. Karkar

A novel series of pyridine–1,3,4-oxadiazole hybrid derivatives was synthesized using both conventional and microwave-assisted techniques. The synthetic route involved condensation of isoniazid with various substituted aromatic aldehydes to form hydrazones, followed by cyclization and acetylation in the presence of acetic anhydride. Microwave-assisted synthesis offered significantly higher yields and shorter reaction times compared to conventional methods, supporting a greener approach. The synthesized compounds were characterized using IR, ¹H NMR, ¹³C NMR, and mass spectrometry. Biological screening revealed that compounds bearing electron-donating groups exhibited notable antibacterial activity, while fluoro-substituted analogues demonstrated superior antifungal potency. Cytotoxicity studies confirmed their safety with negligible activity against HeLa cells. Molecular docking studies supported the antimicrobial results, indicating strong binding affinities toward topoisomerase IV and CYP51. Overall, the results highlight pyridine–1,3,4-oxadiazole hybrids as promising scaffolds for future antimicrobial drug development.

采用常规技术和微波辅助技术合成了一系列新的吡啶- 1,3,4-恶二唑杂化衍生物。合成路线包括异烟肼与各种取代的芳香醛缩合形成腙，然后在乙酸酐存在下进行环化和乙酰化。与传统方法相比，微波辅助合成具有更高的收率和更短的反应时间，支持更环保的方法。合成的化合物通过IR、1H NMR、13C NMR和质谱进行了表征。生物筛选表明，含供电子基团的化合物具有显著的抗菌活性，而含氟取代的类似物具有更强的抗真菌效力。细胞毒性研究证实了其安全性，对HeLa细胞的活性可以忽略不计。分子对接研究支持抗菌结果，表明对拓扑异构酶IV和CYP51具有很强的结合亲和力。总之，这些结果突出了吡啶- 1,3,4-恶二唑复合物是未来抗菌药物开发的有前途的支架。

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引用次数: 0

Synthesis of 2-carboxamide-substituted benzimidazoles via S8-promoted multicomponent reaction in aqueous media s8催化多组分反应合成2-羧酰胺取代苯并咪唑

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-01-03 DOI: 10.1016/j.tet.2025.135130

Valentina Birukova, Anatoly Y. Chursin, Igor V. Zavarzin, Yulia A. Volkova

A novel approach to the synthesis of 2-carboxamide-substituted benzimidazoles from a wide range of 1,2-diamines and 2-functionalized acetamides was developed via elemental sulfur promoted cascade reaction. This procedure provides an efficient and facile route to benzimidazoles from readily available substrates under mild reaction conditions. The protocol is distinguished by efficiency in water and good tolerance to functional groups.

采用单质硫促进级联反应，以1,2-二胺和2-功能化乙酰酰胺为原料合成2-羧基取代苯并咪唑。该方法在温和的反应条件下，从现成的底物制备苯并咪唑提供了一种高效、简便的途径。该方案的特点是在水中的效率和对官能团的良好耐受性。

引用次数: 0

Tandem/domino reactions in glycoscience to access diverse glycohybrids: Recent developments and future perspective 糖科学中的串联/多米诺反应获取多种糖杂化物：最新进展和未来展望

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-31 DOI: 10.1016/j.tet.2025.135129

Danish Ansari , Mangal S. Yadav , Anindra Sharma , Sanchayita Rajkhowa , Shristy Maurya , Supriya Singh , Vinod K. Tiwari

Carbohydrates, due to their inherent chirality, high functional group density, and structural diversity, have emerged as powerful scaffolds in MCR-tandem synthesis of biologically relevant molecules. These naturally occurring polyhydroxy compounds offer a versatile platform for the rapid generation of complex molecular architectures with high stereochemical fidelity. In MCR tandem reactions, carbohydrate-derived molecular scaffolds may facilitate efficient bond-forming sequences by enabling multiple transformations in a single synthetic operation, often under mild reaction conditions. The role of sugar-based scaffolds further extends from passive frameworks to active participants in reaction mechanisms that eventually influence their regio- and stereoselectivity to demonstrate the utilities in synthesizing biologically active molecules, natural product mimetic, and glycomimetics. This review discusses the emerging aspects of Domino approach to enhance the synthetic efficiency and atom economy, aligning with the principles of green chemistry that make such carbohydrate-based tandem strategies increasingly attractive in organic synthesis along with future perspectives.

碳水化合物由于其固有的手性、高官能团密度和结构多样性，已成为mcr -串联合成生物相关分子的有力支架。这些天然存在的多羟基化合物为快速生成具有高立体化学保真度的复杂分子结构提供了一个多功能平台。在MCR串联反应中，通常在温和的反应条件下，碳水化合物衍生的分子支架可以在一次合成操作中实现多次转化，从而促进有效的键形成序列。糖基支架的作用进一步从被动框架扩展到反应机制的主动参与者，最终影响其区域和立体选择性，以证明其在合成生物活性分子、天然产物模拟物和糖模拟物方面的实用性。这篇综述讨论了多米诺方法在提高合成效率和原子经济性方面的新兴方面，与绿色化学的原则相一致，使这种基于碳水化合物的串联策略在有机合成中越来越有吸引力，并具有未来的前景。

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引用次数: 0

Recent developments in C–H functionalization of azauracils 杜鹃花C-H功能化研究进展

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-30 DOI: 10.1016/j.tet.2025.135128

Juanjuan Wu , Leilei Wang , Kelu Yan

Azauracils, as an important class of nitrogen-containing aromatics, exhibits a wide range of pharmaceutical and biological activities. The structural modification and functionalization of these compounds have emerged as a prominent research focus in contemporary organic synthesis. This review systematically summarizes the latest developments in direct C–H alkylation, arylation, acylation, phosphonation, borylation, silylation, and fluoroalkylation of azauracil derivatives. The characteristics of these transformations, substrate universality, synthetic applications, and reaction mechanisms are emphasized. In addition, potential research directions in this field are discussed, aiming to provide theoretical insights for the development and application of therapeutic agents.

杜鹃花是一类重要的含氮芳香化合物，具有广泛的药用和生物活性。这些化合物的结构修饰和功能化已成为当代有机合成领域的一个重要研究热点。本文系统地综述了杜鹃花酸衍生物的直接碳氢烷基化、芳基化、酰化、膦化、硼基化、硅基化和氟烷基化的最新进展。强调了这些转化的特点、底物的普遍性、合成应用和反应机理。并对该领域潜在的研究方向进行了探讨，旨在为治疗剂的开发和应用提供理论指导。

引用次数: 0

Palladium-catalyzed decarbonylative alkynylation of hydroxyquinoline carboxylic acid using dual C–H/C–O bond activation 钯催化羟基喹啉羧酸的脱羰烷基化反应

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-26 DOI: 10.1016/j.tet.2025.135127

Zebabanu Khalifa, Amit B. Patel

A versatile, atom-efficient, and sustainable decarbonylative Sonogashira cross-coupling approach has been disclosed by optimizing a range of palladium catalytic systems for enabling the direct construction of a C(sp²)-C(sp) bond between 4-hydroxyquinoline-3-carboxylic acid derivatives and structurally diverse terminal alkynes via dual C–O/C–H functionalization. This facile protocol has offered significant economic value due to its in situ functionality and well-tolerable substrate scopes, which provide reasonable yields up to 88 % with minimal byproduct generation. Also, mechanistic investigation revealed the efficiency of the palladium-ligand active species, which evolved valuable insights for the decarbonylative C(sp²)-C(sp) cross-coupling pathway within a single catalytic system. Hence, this present study introduces an operatively reliable and sustainable route for the late-stage functionalization of N-heteroaromatic scaffolds, offering significant potential for material synthesis, molecular diversification, and chemotherapeutic innovations by involving palladium-catalyzed decarbonylative Sonogashira cross-coupling.

通过优化一系列钯催化体系，揭示了一种通用的、原子高效的、可持续的脱碳Sonogashira交叉偶联方法，该方法可以通过双C - o /C -h功能化在4-羟基喹啉-3-羧酸衍生物和结构多样的末端炔之间直接构建C(sp2)-C（sp）键。由于其原位功能和良好的耐受底物范围，这种简单的方案提供了显着的经济价值，可提供高达88%的合理产率，并且产生最少的副产品。此外，机理研究揭示了钯配体活性物质的效率，为单一催化体系中脱羰C(sp2)-C（sp）交叉偶联途径提供了有价值的见解。因此，本研究为n -杂芳烃支架的后期功能化提供了一条可靠和可持续的途径，通过钯催化脱碳Sonogashira交叉偶联，为材料合成、分子多样化和化疗创新提供了巨大的潜力。

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引用次数: 0

Phosphorus-based redox organocatalysis for sustainable synthesis: A literature review 基于磷的氧化还原有机催化可持续合成：文献综述

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-26 DOI: 10.1016/j.tet.2025.135124

Raphaël El Bekri-Saudain , Pierre-Olivier Butin , Lucas Mele , Louise Fourbet, Louise Musikas, David Virieux, Tahar Ayad

Fundamental transformations in organic synthesis, such as the Wittig, Staudinger, Appel and Mitsunobu reactions, have traditionally relied on stoichiometric amounts of phosphine, leading to phosphine oxide by-products. Due to their high stability and polarity, these oxides complicate purification processes and diminish overall reaction efficiency. In 2015, members of the American Chemical Society emphasized the need to develop methodologies that minimize or eliminate phosphine oxide waste. This call to action has since spurred widespread innovation and driven numerous research groups to reassess their synthetic approaches. This review highlights recent advances over the past two decades in phosphorus-based redox organocatalysis, which represent a promising direction for expanding the scope and sustainability of phosphorus-mediated transformations.

有机合成中的基本转变，如Wittig、Staudinger、Appel和Mitsunobu反应，传统上依赖于化学计量量的磷化氢，从而产生氧化磷化氢的副产品。由于它们的高稳定性和极性，这些氧化物使纯化过程复杂化，降低了整体反应效率。2015年，美国化学会（American Chemical Society）的成员强调，有必要开发出减少或消除氧化膦废物的方法。这一行动呼吁激发了广泛的创新，并促使许多研究小组重新评估他们的综合方法。这篇综述强调了过去二十年来磷基氧化还原有机催化的最新进展，这代表了扩大磷介导转化的范围和可持续性的有希望的方向。

引用次数: 0

Nickel photocatalytic aryl halide and amine C–N bond coupling 镍光催化芳基卤化物与胺C-N键偶联

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-25 DOI: 10.1016/j.tet.2025.135107

Sazia Sultana, Ryan Eleveld, Md Matiar Rahman, Aaron L. Odom

Aryl bromides and iodides can be coupled with primary and secondary amines using NiBr₂ and DABCO in DMA or DMSO with 427 nm light, without the use of palladium, expensive phosphines, or photoredox catalysts. The reactions are very sensitive to the solvent used, with some reactions working in DMA and others in DMSO for reasons that are currently unknown. An NRF2 inhibitor, ZH-71, was prepared using the method, which required a mixture of DMA and DMSO for the reaction to proceed. The reactions can be optimized to excellent yields and work with a large range of substrates.

芳基溴化物和碘化物可以在427 nm光下使用NiBr2和DABCO在DMA或DMSO中与伯胺和仲胺偶联，而无需使用钯、昂贵的磷化氢或光氧化还原催化剂。这些反应对所使用的溶剂非常敏感，有些反应在DMA中起作用，有些反应在DMSO中起作用，原因目前尚不清楚。用该方法制备了NRF2抑制剂ZH-71，该方法需要DMA和DMSO的混合物才能进行反应。该反应可以优化到优异的产率，并适用于大范围的底物。

引用次数: 0

Synthesis of novel naphthopyran dyes and their photochromic properties in resin lenses 新型萘吡喃染料的合成及其在树脂透镜中的光致变色性能

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-24 DOI: 10.1016/j.tet.2025.135126

Qin Li , Shanglin Li , Zhouyang Long , Minyi Liang , Zihao Yin , Pingbo Zhang , Yan Leng

Naphthopyran compounds represent a significant category of photochromic molecules that can reversibly change color when exposed to UV light and have been extensively utilized in ophthalmic lenses. However, the slow adaptation from a colored state to a colorless state in the absence of UV light is one of the limitations. Herein, we have designed and synthesized a series of naphthopyran dyes with varying substituent modifications. Our findings indicate that expanding the conjugated structure of naphthopyran and introducing a –OH group at the indeno bridge can effectively adjust the visible spectrum of the dye and increase the photosensitivity of the ring-opening and ring-closing reaction. This leads to the production of more vivid green hues and facilitates a swift transition between the colorless and colored states. The clear photochromic-photovoltaic structure-property relationships for these naphthopyran dyes are established by DFT calculation, and they are shown to demonstrate sensitive photochromic responses in resin lenses.

萘吡喃化合物是一类重要的光致变色分子，当暴露在紫外线下时可以可逆地改变颜色，并已广泛用于眼科镜片。然而，在没有紫外线的情况下，从有色状态到无色状态的缓慢适应是限制之一。在此，我们设计并合成了一系列具有不同取代基修饰的萘吡喃染料。研究结果表明，扩大萘吡喃的共轭结构，在吲哚桥上引入-OH基团，可以有效地调节染料的可见光谱，提高开环和闭环反应的光敏性。这导致产生更生动的绿色色调，并促进无色和彩色状态之间的快速过渡。通过DFT计算建立了这些萘吡喃染料清晰的光致变色-光伏结构-性能关系，并表明它们在树脂透镜中表现出敏感的光致变色响应。

引用次数: 0

Self-assembly of neural-like nanotubular network architectures from diacetylene lipid vesicles 二乙炔脂质囊泡自组装神经样纳米管网络结构

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-24 DOI: 10.1016/j.tet.2025.135125

Vachiraporn Ajavakom , Suricha Pumtang , Waraluck Chaichompoo , Wachirachai Pabuprapap , Chanyathorn Ruamyart , Anawat Ajavakom , Mongkol Sukwattanasinitt , Ken-ichi Shinohara

The self-assembly behavior of a newly synthesized amphiphilic diacetylene compound, 4-oxo-4-(pentacosa-10,12-diynylamino)butanoic acid (PCDAS), was investigated in aqueous media. Upon UV irradiation followed by incubation at ambient temperature, PCDAS gradually transformed from spherical vesicular nanoparticles into interconnected single-walled nanotube (SWNT)-based neural-like nanotubular networks (NNNs). The formation of these branched architectures is driven by the progressive co-fusion and reorganization of vesicular assemblies. A three-stage mechanism was proposed for this transformation: (1) vesicle aggregation through head-to-head hydrophilic interactions, (2) propagation into elongated nanotubular assemblies via vesicle fusion and molecular reorganization, and (3) interconnection of nanotubes to construct a continuous NNN. High-resolution atomic force microscopy (AFM) imaging under air revealed bilayer-type junctions with heights of approximately 5–6 nm, while the connecting nanotubes exhibited heights of around 1 nm, characteristic of single-walled structures. The thermal stability of the NNN was relatively high, as it preserved its morphology even when subjected to elevated temperatures under ambient conditions on mica substrates. These results highlight the potential of this self-assembled nanostructure for applications in composite materials, reinforced plastics, and advanced industrial coatings.

研究了新合成的两亲性二乙炔化合物4-氧-4-（五羧基-10,12-二氨基）丁酸（PCDAS）在水介质中的自组装行为。经过紫外线照射和室温培养，PCDAS逐渐从球形囊状纳米颗粒转变为基于单壁纳米管（SWNT）的互联神经样纳米管网络（NNNs）。这些分支结构的形成是由囊泡组装的渐进融合和重组驱动的。提出了这种转变的三个阶段机制：(1)通过头对头的亲水性相互作用实现囊泡聚集；(2)通过囊泡融合和分子重组传播成细长的纳米管组件；(3)纳米管互连以构建连续的神经网络。空气环境下的高分辨率原子力显微镜（AFM）成像显示双层型结的高度约为5-6 nm，而连接的纳米管的高度约为1 nm，具有单壁结构的特征。NNN的热稳定性相对较高，因为即使在云母衬底的环境条件下温度升高，它也能保持其形态。这些结果突出了这种自组装纳米结构在复合材料、增强塑料和先进工业涂料中的应用潜力。

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引用次数: 0

Blue TADF fluorescence emitter with AIE property and narrow emission in OLED applications 具有AIE特性和窄发射的蓝色TADF荧光发射器在OLED中的应用

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-12-23 DOI: 10.1016/j.tet.2025.135109

Xiaoling Niu , Wenlong Qu , Haoyu Ma , Tiantian Ma , Zhen Feng , Shengbo Zhu

Obtaining blue fluorescence emission, easy synthesis, excellent color purity, non-doped emitters has drawn great interest in the application of organic light emitting diodes (OLEDs). Thermally activated delayed fluorescence (TADF) and aggregation-induced emission (AIE) are two promising performance to realize high-efficiency and non-doped OLEDs. Herein, a blue fluorescence emitter of Cz-Trz-CN is designed and synthesized using carbazole derivative as a donor unit and triazine derivative as an acceptor unit by one-step reaction. It exhibits obvious AIE and TADF properties, and narrow emission in OLED applications. The photophysical experiments and the density functional theory (DFT) and time-DFT theoretical studies were used to confirm the AIE and TADF properties of Cz-Trz-CN. The OLEDs performances based on Cz-Trz-CN (nondoped), (doped as guest), and (doped as host) were studied systematically, which exhibited blue emission with CIE coordinates (0.1282, 0.0818), (0.1327, 0.0633) and (0.1249, 0.1135), respectively, and narrow full width at half maximum (FWHM) of 22.0 nm, 21.0 nm and 20.6 nm, respectively. The results show that the AIE and TADF properties are attribute to the highly twisted molecular conformation. This study provide a new method for developing high efficiency, color purity and non-doped OLED emitters.

获得蓝色荧光发射、易于合成、色纯度优异、无掺杂的发光体已引起人们对有机发光二极管（oled）应用的极大兴趣。热激活延迟荧光（TADF）和聚集诱导发光（AIE）是实现高效非掺杂oled的两种有前途的技术。本文以咔唑衍生物为给体单元，三嗪衍生物为受体单元，通过一步反应设计合成了Cz-Trz-CN的蓝色荧光发射器。它具有明显的AIE和TADF特性，在OLED应用中具有窄发射特性。利用光物理实验、密度泛函理论（DFT）和时间泛函理论研究证实了Cz-Trz-CN的AIE和TADF性质。系统地研究了Cz-Trz-CN（未掺杂）、（作为客体掺杂）和（作为主体掺杂）的有机发光二极管的性能，分别表现出CIE坐标为（0.1282,0.0818）、（0.1327,0.0633）和（0.1249,0.1135）的蓝色发光，半峰全宽分别为22.0 nm、21.0 nm和20.6 nm。结果表明，AIE和TADF的性质与分子的高度扭曲构象有关。该研究为开发高效、纯色、无掺杂的OLED发光材料提供了新的途径。

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