Tetrahedron最新文献

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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 : 2026-04-01 Epub 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

One-step construction of 1-aroyl-2-methylbenzimidazoles using solid calcium carbide as a C2 source 以固体电石为C2源一步法合成1-芳烃-2-甲基苯并咪唑

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-04-01 Epub Date: 2025-12-23 DOI: 10.1016/j.tet.2025.135122

Ting Shao , Botao Wang , Jinhui Yang , Zheng Li

A concise method for the construction of 1-aroyl-2-methylbenzimidazoles using solid calcium carbide as a C2 source, N-(2-aminophenyl)benzamides as substrates, tosyl azides as a mediator, through a one-step procedure is described. The target products were effectively obtained through cascade annulations, involving the one-step formation of two C–N bonds. The salient features for this protocol are the use of inexpensive, abundant, and easy-to-handle solid C2 source, easily synthesized reactants, low-cost catalyst, wide functional tolerance, satisfactory yield, and simple workup procedure. The reactions can also be carried out on a gram scale.

介绍了以固体电石为C2源，N-（2-氨基苯基）苯酰胺为底物，tosyyl叠氮化物为介质，一步合成1-芳基-2-甲基苯并咪唑的简明方法。目标产物通过级联环有效地获得，涉及一步形成两个C-N键。该方案的突出特点是使用廉价、丰富、易于处理的固体C2源、容易合成的反应物、低成本的催化剂、广泛的功能耐受性、令人满意的产率和简单的后处理程序。这些反应也可以以克为单位进行。

引用次数: 0

Copper-catalyzed/mediated synthesis of thiophenes and benzothiophenes: an updated review 铜催化/介导合成噻吩和苯并噻吩的最新进展

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-12-08 DOI: 10.1016/j.tet.2025.135089

Rajaghatta N. Suresh , Toreshettahally R. Swaroop , Kanchugarakoppal S. Rangappa

Copper-catalyzed/mediated synthesis of heterocycles plays a crucial role in the field of medicinal chemistry as well as synthetic organic chemistry. Notably, copper salts facilitate the C-S bond formation during the synthesis of heterocycles. On the other hand, they also serve as oxidizing agents, metal catalysts and Lewis acids. This review summarizes an updated collection of copper-catalyzed/mediated synthesis of thiophenes and benzothiophenes. Furthermore, optimal reaction conditions, reaction's scope/generality, pros and/or cons, discussion of control experiments and plausible mechanisms of the reactions are presented. In addition, this review article collects important strategies of copper-catalyzed/mediated synthesis of thiophenes and benzothiophenes reported from 2010 to 2024, which is advantageous for many chemists interested in transition metal-catalyzed reactions.

铜催化/介导的杂环化合物的合成在药物化学和合成有机化学领域有着重要的作用。值得注意的是，铜盐在杂环合成过程中促进了C-S键的形成。另一方面，它们也可用作氧化剂、金属催化剂和路易斯酸。本文综述了铜催化/介导合成噻吩和苯并噻吩的最新研究进展。此外，还介绍了反应的最佳条件、反应的范围/普遍性、优点和缺点、控制实验的讨论和反应的合理机理。此外，本文还收集了2010年至2024年报道的铜催化/介导合成噻吩和苯并噻吩的重要策略，这对许多对过渡金属催化反应感兴趣的化学家来说是有利的。

引用次数: 0

Mild and regioselective iodination of 3,5-disubstituted isothiazoles with N-iodosuccinimide and trifluoroacetic acid 用n -碘琥珀酰亚胺和三氟乙酸对3,5-二取代异噻唑进行轻度和区域选择性碘化

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-11-22 DOI: 10.1016/j.tet.2025.135068

Wen Yang , Ziyi Xu , Jiawei Bai , Hongyu Qiu , Zhongzhong Cao , Xin Min , Xuerui Yang , ChangChao Zhan , Qingchun Huang , Jiayan Pan , Zhongxin Li , Lidong Lai , Shaomin Ji

Combining N-iodosuccinimide (NIS) and trifluoroacetic acid (TFA) offers an efficient method for the iodination of a wide range of 3,5-disubstituted isothiazoles at room temperature, as demonstrated in this paper. The results indicate that when the C5 position of isothiazole ring is not the substituent of OCH₃Ph, the corresponding C4-mono-iodoisothiazoles are obtained in high yields with excellent regioselectivity, while when the C5 position of isothiazole ring is the substituent of OCH₃Ph, the corresponding diiodo and triiodoisothiazoles were synthesized. Additionally, both of bromination and chlorination of 3,5-disubstituted isothiazoles can also occur efficiently. Moreover, the versatility of the method is demonstrated by the iodination of isoxazoles and isoselenazoles.

结合n -碘琥珀酰亚胺（NIS）和三氟乙酸（TFA）提供了一种在室温下广泛的3,5-二取代异噻唑碘化的有效方法。结果表明，当异噻唑环的C5位置不是OCH3Ph取代基时，可以高收率地合成相应的c4 -单碘异噻唑，且具有良好的区域选择性；当异噻唑环的C5位置是OCH3Ph取代基时，可以合成相应的二碘和三碘异噻唑。此外，3,5-二取代异噻唑的溴化和氯化反应也能有效发生。此外，通过异恶唑和异硒化唑的碘化证明了该方法的通用性。

引用次数: 0

Synthesis of symmetric aryl sulfides mediated by xanthates: Based on the EDA complex strategy 黄原酸介导对称芳基硫化物的合成：基于EDA配合物策略

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-12-14 DOI: 10.1016/j.tet.2025.135105

Lisha Wu, Xue Li, DongXiang Yan, Kun Cao, Jiahong Li

An efficient method for symmetric aryl sulfides synthesis is reported. Using low-cost, readily available potassium xanthogenate as sulfur source, it reacts with aryl bromides under light, possibly via two EDA interactions. Potassium xanthogenate acts as electron donor in the first EDA complex and generates key thiophenolate anion. It accesses hard-to-obtain electron-deficient products, tolerates diverse functional groups, and opens new avenues for diaryl sulfides.

报道了一种合成对称芳基硫化物的有效方法。它使用低成本、容易获得的黄原酸钾作为硫源，在光照下与芳基溴发生反应，可能通过两种EDA相互作用。黄原酸钾作为第一个EDA复合物的电子供体，生成关键的硫酚酸阴离子。它获得难以获得的缺电子产物，耐受多种官能团，并为二芳基硫化物开辟了新的途径。

引用次数: 0

Brønsted acid-promoted selective addition of chromones with H-phosphine oxides for synthesis of C2-Phosphorylated 2,3-2H-chromones Brønsted酸促进与h -膦氧化物选择性加成以合成c2磷酸化2,3- 2h -铬

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-12-11 DOI: 10.1016/j.tet.2025.135096

Huabin Wang , Qiaoli Li , Feiyang Long , Tiantian Zhou , Zeyu Zhang , Songlin Zhang , Zhen Yao , Ying Zhou , Qiang Huang

An efficient and eco-friendly protocol to synthesize C2-phosphorylated 2,3-dihydrochromones was developed via Brønsted acid-promoted selective addition of chromones with H-phosphine oxides. The reaction exhibits a broad substrate scope, shows good compatibility with various functional groups, affords high yields and is amenable to gram - scale synthesis. This strategy, mediated by Brønsted acid, proceeded smoothly under mild and simple conditions without any metal catalyst or oxidant, providing an alternative approach to access C2-phosphorylated 2,3-dihydrochromones.

采用Brønsted酸促进h -膦氧化物选择性加成法制备了一种高效、环保的c2磷酸化2,3-二氢铬。该反应底物范围广，与多种官能团相容性好，产率高，适于克级合成。该策略由Brønsted酸介导，在温和和简单的条件下顺利进行，不需要任何金属催化剂或氧化剂，为获得c2磷酸化的2,3-二氢铬酮提供了另一种途径。

引用次数: 0

Characterization of two diterpene synthases from Chitinophaga species 食几丁菌两种二萜合成酶的性质

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-12-12 DOI: 10.1016/j.tet.2025.135091

Xi Xiang , Minghui Xie , Hongran Chen , Zixin Deng , Gen Li , Xiaohui Yan , Min Xu , Anwei Hou

Bacterial terpene synthases (TPSs) represent a valuable source of enzymatic diversity for the discovery of novel terpenoid structures. Here, we report the functional characterization of two diterpene synthases, GTC2 and E2E2, from Chitinophaga species. Heterologous expression and biochemical assays demonstrated that both enzymes can utilize farnesyl diphosphate (FPP) and geranylgeranyl diphosphate (GGPP) to produce distinct terpene profiles. Six diterpenes (5–10) were isolated, including two new compounds (8 and 9), for which their structures and relative configurations were elucidated and plausible formation mechanisms were proposed. Structural modeling, molecular docking, and mutagenesis revealed that residue Y293 plays a key role in determining the product specificity of E2E2. Y293 N substitution significantly altered the product profile, affording three known diterpenes (11–13), one of which (11) was confirmed by X-ray crystallography. This study expands the known diterpene diversity of Chitinophaga and provides insights into the structure–function relationship of bacterial diterpene synthases.

细菌萜烯合成酶（tps）为发现新的萜类结构提供了一个有价值的酶多样性来源。本文报道了食几丁菌中两种二萜合成酶GTC2和E2E2的功能特征。异种表达和生化实验表明，这两种酶都可以利用法尼基二磷酸（FPP）和香叶基二磷酸（GGPP）产生不同的萜烯谱。分离得到6个二萜化合物（5 ~ 10），其中包括2个新化合物（8和9），并对它们的结构和相对构型进行了解析，提出了可能的形成机理。结构建模、分子对接和诱变表明，残基Y293在决定E2E2产物特异性中起关键作用。Y293 N的取代显著改变了产物的结构，得到了三个已知的二萜（11 - 13），其中一个（11）通过x射线晶体学得到了证实。本研究扩展了已知的几丁食虫二萜多样性，并对细菌二萜合成酶的结构-功能关系提供了新的见解。

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引用次数: 0

Tuning the reactivity of benzylic radicals by virtue of the presence of an acid/ester functional group at the benzylic carbon 通过在苯基碳上存在酸/酯官能团来调整苯基自由基的反应性

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-12-01 DOI: 10.1016/j.tet.2025.135086

Upma Gulati , Anjali Gupta, Joydev K. Laha

A classical transformation involving benzylic oxidation is developed using a metal-free approach. Unlike the reported methods, this report unveils for the first time the synthesis of arylglyoxylic esters from arylacetic esters utilizing the TBN/NHS catalytic system. A variety of substrates in moderate to good yields (up to 85 %) are synthesized to exhibit the practical applicability of the reaction. The synthesized products display great utility and value in terms of synthetic transformations including the synthesis of many useful scaffolds. Mechanistic studies reveal the formation of a benzylic functionalized nitro compound as active intermediate leading to the formation of desired product.

使用无金属方法开发了涉及苯氧化的经典转化。与报道的方法不同，本报告首次揭示了利用TBN/NHS催化体系从芳基乙酸酯合成芳基乙醛酯的方法。合成了多种产率中等至良好（高达85%）的底物，以显示该反应的实际适用性。合成产物在合成转化方面具有很大的实用性和价值，包括合成许多有用的支架。机理研究揭示了苯基官能化硝基化合物的形成作为活性中间体导致所需产物的形成。

引用次数: 0

Access to 2-aminoquinolines from 2-vinylanilines and isothiocyanates via electrochemically induced desulfurative cyclization 通过电化学诱导脱硫环化从2-乙烯苯胺和异硫氰酸酯中获得2-氨基喹啉

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-11-25 DOI: 10.1016/j.tet.2025.135069

Wenxue Li , Zhenjie Qi , Zhenyu An , Yinjun Wei , Boyue Lin , Wenxin Chen , Yafeng Liu

An efficient electrochemical oxidation cyclization of 2-vinylanilines and isothiocyanates has been achieved for the synthesis of 2-aminoquinolines via NaI-mediated desulfurative cyclization. The protocol is further characterized by its high yield, broad substrate scope, and operational simplicity. Mechanistic studies reveal that the reaction involves the formation of a thiourea intermediate from 2-vinylanilines and isothiocyanates under electrochemical oxidation.

通过nai介导的脱硫环化，实现了2-乙烯基苯胺和异硫氰酸酯的高效电化学氧化环化合成2-氨基喹啉。该协议的进一步特点是其高收率，广泛的衬底范围和操作简单。机理研究表明，该反应涉及2-乙烯苯胺和异硫氰酸酯在电化学氧化作用下生成硫脲中间体。

引用次数: 0

Synthesis of 2,3-dihydrothiazole-5-carboxylates via a domino reaction of tetralone-derived β-ketothioamides with nitroallylic acetates 四酮衍生β-酮硫胺与硝酸基乙酸酯多米诺反应合成2,3-二氢噻唑-5-羧酸盐

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2026-03-01 Epub Date: 2025-12-13 DOI: 10.1016/j.tet.2025.135098

Gang Wang , Jianpeng Du , Jian Liu , Jiangtao Li , Xiaohua Wang , Lin Zhang , Yalan Feng , Minglan Ma

An unprecedented metal-free cyclization reaction of tetralone-derived β-ketothioamides with nitroallylic acetates was developed, which provided a powerful method for the synthesis of 2,3-dihydrothiazole-5-carboxylates. In the reaction, nitroallylic acetates used α,β-carbons rather than the β,γ-carbons to construct the five-membered thiazole ring. The protocol features good functional group tolerance, mild metal-free conditions and simple procedure.

研究了四酮类β-酮硫酰胺与硝酸基乙酸酯的无金属环化反应，为2,3-二氢噻唑-5-羧酸酯的合成提供了有力的方法。在反应中，硝基乙酸酯用α、β-碳而不是β、γ-碳来构建五元噻唑环。该方案具有良好的官能团耐受性，温和的无金属条件和简单的程序。

引用次数: 0

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