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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
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
{"title":"Self-assembly of neural-like nanotubular network architectures from diacetylene lipid vesicles","authors":"Vachiraporn Ajavakom ,&nbsp;Suricha Pumtang ,&nbsp;Waraluck Chaichompoo ,&nbsp;Wachirachai Pabuprapap ,&nbsp;Chanyathorn Ruamyart ,&nbsp;Anawat Ajavakom ,&nbsp;Mongkol Sukwattanasinitt ,&nbsp;Ken-ichi Shinohara","doi":"10.1016/j.tet.2025.135125","DOIUrl":"10.1016/j.tet.2025.135125","url":null,"abstract":"<div><div>The self-assembly behavior of a newly synthesized amphiphilic diacetylene compound, 4-oxo-4-(pentacosa-10,12-diynylamino)butanoic acid (<strong>PCDAS</strong>), was investigated in aqueous media. Upon UV irradiation followed by incubation at ambient temperature, <strong>PCDAS</strong> 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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135125"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838238","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"One-step construction of 1-aroyl-2-methylbenzimidazoles using solid calcium carbide as a C2 source","authors":"Ting Shao ,&nbsp;Botao Wang ,&nbsp;Jinhui Yang ,&nbsp;Zheng Li","doi":"10.1016/j.tet.2025.135122","DOIUrl":"10.1016/j.tet.2025.135122","url":null,"abstract":"<div><div>A concise method for the construction of 1-aroyl-2-methylbenzimidazoles using solid calcium carbide as a C2 source, <em>N</em>-(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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135122"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838241","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Copper-catalyzed/mediated synthesis of thiophenes and benzothiophenes: an updated review","authors":"Rajaghatta N. Suresh ,&nbsp;Toreshettahally R. Swaroop ,&nbsp;Kanchugarakoppal S. Rangappa","doi":"10.1016/j.tet.2025.135089","DOIUrl":"10.1016/j.tet.2025.135089","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135089"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733905","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Mild and regioselective iodination of 3,5-disubstituted isothiazoles with N-iodosuccinimide and trifluoroacetic acid","authors":"Wen Yang ,&nbsp;Ziyi Xu ,&nbsp;Jiawei Bai ,&nbsp;Hongyu Qiu ,&nbsp;Zhongzhong Cao ,&nbsp;Xin Min ,&nbsp;Xuerui Yang ,&nbsp;ChangChao Zhan ,&nbsp;Qingchun Huang ,&nbsp;Jiayan Pan ,&nbsp;Zhongxin Li ,&nbsp;Lidong Lai ,&nbsp;Shaomin Ji","doi":"10.1016/j.tet.2025.135068","DOIUrl":"10.1016/j.tet.2025.135068","url":null,"abstract":"<div><div>Combining <em>N</em>-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 OCH<sub>3</sub>Ph, 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 OCH<sub>3</sub>Ph, 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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135068"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145584308","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Synthesis of symmetric aryl sulfides mediated by xanthates: Based on the EDA complex strategy","authors":"Lisha Wu,&nbsp;Xue Li,&nbsp;DongXiang Yan,&nbsp;Kun Cao,&nbsp;Jiahong Li","doi":"10.1016/j.tet.2025.135105","DOIUrl":"10.1016/j.tet.2025.135105","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135105"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786970","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Tuning the reactivity of benzylic radicals by virtue of the presence of an acid/ester functional group at the benzylic carbon","authors":"Upma Gulati ,&nbsp;Anjali Gupta,&nbsp;Joydev K. Laha","doi":"10.1016/j.tet.2025.135086","DOIUrl":"10.1016/j.tet.2025.135086","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135086"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733907","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Brønsted acid-promoted selective addition of chromones with H-phosphine oxides for synthesis of C2-Phosphorylated 2,3-2H-chromones","authors":"Huabin Wang ,&nbsp;Qiaoli Li ,&nbsp;Feiyang Long ,&nbsp;Tiantian Zhou ,&nbsp;Zeyu Zhang ,&nbsp;Songlin Zhang ,&nbsp;Zhen Yao ,&nbsp;Ying Zhou ,&nbsp;Qiang Huang","doi":"10.1016/j.tet.2025.135096","DOIUrl":"10.1016/j.tet.2025.135096","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135096"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Characterization of two diterpene synthases from Chitinophaga species","authors":"Xi Xiang ,&nbsp;Minghui Xie ,&nbsp;Hongran Chen ,&nbsp;Zixin Deng ,&nbsp;Gen Li ,&nbsp;Xiaohui Yan ,&nbsp;Min Xu ,&nbsp;Anwei Hou","doi":"10.1016/j.tet.2025.135091","DOIUrl":"10.1016/j.tet.2025.135091","url":null,"abstract":"<div><div>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 <em>Chitinophaga</em> 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 (<strong>5</strong>–<strong>10</strong>) were isolated, including two new compounds (<strong>8</strong> and <strong>9</strong>), 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 (<strong>11</strong>–<strong>13</strong>), one of which (<strong>11</strong>) was confirmed by X-ray crystallography. This study expands the known diterpene diversity of <em>Chitinophaga</em> and provides insights into the structure–function relationship of bacterial diterpene synthases.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135091"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786969","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Synthesis of 2,3-dihydrothiazole-5-carboxylates via a domino reaction of tetralone-derived β-ketothioamides with nitroallylic acetates","authors":"Gang Wang ,&nbsp;Jianpeng Du ,&nbsp;Jian Liu ,&nbsp;Jiangtao Li ,&nbsp;Xiaohua Wang ,&nbsp;Lin Zhang ,&nbsp;Yalan Feng ,&nbsp;Minglan Ma","doi":"10.1016/j.tet.2025.135098","DOIUrl":"10.1016/j.tet.2025.135098","url":null,"abstract":"<div><div>An unprecedented metal-free cyclization reaction of tetralone-derived <em>β</em>-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 <em>α,β</em>-carbons rather than the <em>β,γ</em>-carbons to construct the five-membered thiazole ring. The protocol features good functional group tolerance, mild metal-free conditions and simple procedure.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135098"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786967","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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
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
{"title":"Access to 2-aminoquinolines from 2-vinylanilines and isothiocyanates via electrochemically induced desulfurative cyclization","authors":"Wenxue Li ,&nbsp;Zhenjie Qi ,&nbsp;Zhenyu An ,&nbsp;Yinjun Wei ,&nbsp;Boyue Lin ,&nbsp;Wenxin Chen ,&nbsp;Yafeng Liu","doi":"10.1016/j.tet.2025.135069","DOIUrl":"10.1016/j.tet.2025.135069","url":null,"abstract":"<div><div>An efficient electrochemical oxidation cyclization of 2-vinylanilines and isothiocyanates has been achieved for the synthesis of 2-aminoquinolines <em>via</em> 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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135069"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145682377","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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