Tetrahedron chem最新文献

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Synthesis of novel benzo fused bridged azaheterocycles through the reaction of chalcone with hydrazone 通过查尔酮与腙的反应合成新型苯并熔桥氮杂环
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2025-01-23 DOI: 10.1016/j.tchem.2025.100122
Congyang Li , Ruochen Pang , Weiwu Ren
{"title":"Synthesis of novel benzo fused bridged azaheterocycles through the reaction of chalcone with hydrazone","authors":"Congyang Li ,&nbsp;Ruochen Pang ,&nbsp;Weiwu Ren","doi":"10.1016/j.tchem.2025.100122","DOIUrl":"10.1016/j.tchem.2025.100122","url":null,"abstract":"<div><div>We reported a direct construction of aza-[3.3.1]-bicycles from 2-aminochalcones and hydrazone. Notably, this method formed a potentially biologically active bridged structure containing multiple nitrogen atoms under mild conditions with high yields. This reaction exhibits broad substrate scope and excellent functional group tolerance. This is a new type of benzo fused bridged azaheterocycles, which will be beneficial for further research on this skeleton.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100122"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182682","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Supramolecular light-harvesting systems based on cyanostilbene derivatives 基于氰芪衍生物的超分子光收集系统
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2025-01-20 DOI: 10.1016/j.tchem.2025.100120
Fengyao Cui, Qiaona Zhang, Xiaoman Dang, Tangxin Xiao
{"title":"Supramolecular light-harvesting systems based on cyanostilbene derivatives","authors":"Fengyao Cui,&nbsp;Qiaona Zhang,&nbsp;Xiaoman Dang,&nbsp;Tangxin Xiao","doi":"10.1016/j.tchem.2025.100120","DOIUrl":"10.1016/j.tchem.2025.100120","url":null,"abstract":"<div><div>Photosynthesis provides a natural model for efficient light harvesting, inspiring the development of artificial systems designed to mimic this capability in capturing and converting solar energy. Artificial light-harvesting systems (LHSs) have thus become a key area of research, with promising applications in sensing, imaging, photocatalysis, and optoelectronics. Among the materials explored for LHSs, cyanostilbene derivatives stand out due to their ease of synthesis and unique photophysical properties, such as aggregation-induced emission (AIE) enhancement. These molecules can self-assemble into supramolecular structures through non-covalent interactions, including host–guest interactions, multiple hydrogen bonds, amphiphilic interactions, and metal-ligand coordination, offering tunable architectures for efficient energy transfer and light absorption. This minireview examines recent advancements in the design, synthesis, and functional performance of cyanostilbene-based supramolecular LHSs, analyzing their efficiency and adaptability in energy transfer processes. Future research may focus on integrating these systems with nanomaterials and exploring their potential in advanced energy conversion devices, offering new avenues for sustainable energy technologies.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100120"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182681","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of novel fluorescent 3-pyrrolyl BODIPYs and their derivatives 新型荧光3-吡咯基BODIPYs及其衍生物的合成
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2025-01-22 DOI: 10.1016/j.tchem.2025.100121
Vratta Grover, Mangalampalli Ravikanth
{"title":"Synthesis of novel fluorescent 3-pyrrolyl BODIPYs and their derivatives","authors":"Vratta Grover,&nbsp;Mangalampalli Ravikanth","doi":"10.1016/j.tchem.2025.100121","DOIUrl":"10.1016/j.tchem.2025.100121","url":null,"abstract":"<div><div>3-Pyrrolyl BODIPYs absorb and emit at longer wavelengths with better quantum yields and singlet state lifetimes than BODIPYs due to the presence of an additional pyrrole ring at 3-position. The <em>α</em>-position of the appended pyrrole ring has been functionalized with a wide range of functional groups and these functionalized 3-pyrrolyl BODIPYs are very useful synthons to synthesize several interesting complex 3-pyrrolyl BODIPY-based derivatives. Furthermore, the <em>meso</em>-aryl functionalized 3-pyrrolyl BODIPYs as well as pyrrole functionalized 3-pyrrolyl BODIPYs have also been synthesized and used for the synthesis of a variety of fluorescent 3-pyrrolyl BODIPY-based conjugates. This review article describes different synthetic approaches employed for the synthesis of 3-pyrrolyl BODIPYs, functionalized 3-pyrrolyl BODIPYs and their use in the synthesis of more elaborate 3-pyrrolyl BODIPY-based fluorophores.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100121"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143394986","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation nhc催化heck型C-H叔烷基化构建全碳季中心
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2025-02-25 DOI: 10.1016/j.tchem.2025.100124
Tinglan Liu , Pan Yue , Chengming Wang
{"title":"Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation","authors":"Tinglan Liu ,&nbsp;Pan Yue ,&nbsp;Chengming Wang","doi":"10.1016/j.tchem.2025.100124","DOIUrl":"10.1016/j.tchem.2025.100124","url":null,"abstract":"<div><div>A variety of alkylated alkenes with all-carbon quaternary centers were regioselectively accessed by Heck-type radical NHC catalysis. The herein-developed methodology may contribute to the efficient and rapid construction of various pharmaceuticals and natural products.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100124"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143619107","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Acylbenzo[b]thiophenes, benzofurans and indoles via intramolecular oxidative cyclization enabled by photocatalytic hydrogen atom transfer (HAT) 通过光催化氢原子转移 (HAT) 分子内氧化环化合成酰基苯并[b]噻吩、苯并呋喃和吲哚
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2025-01-04 DOI: 10.1016/j.tchem.2025.100119
Fen-Dou Wang , Jin Jiang , Tiantian Xu , Wen-Chao Yang , Shu-Peng Zhang , Min Wang , Pinhua Li
{"title":"Synthesis of Acylbenzo[b]thiophenes, benzofurans and indoles via intramolecular oxidative cyclization enabled by photocatalytic hydrogen atom transfer (HAT)","authors":"Fen-Dou Wang ,&nbsp;Jin Jiang ,&nbsp;Tiantian Xu ,&nbsp;Wen-Chao Yang ,&nbsp;Shu-Peng Zhang ,&nbsp;Min Wang ,&nbsp;Pinhua Li","doi":"10.1016/j.tchem.2025.100119","DOIUrl":"10.1016/j.tchem.2025.100119","url":null,"abstract":"<div><div>An efficient strategy for intramolecular oxidative cyclization of 2-alkynylthioanisoles toward 3-acylbenzo[<em>b</em>]thiophenes by photochemical hydrogen atom transfer catalysis has been developed. 3-Acylbenzo[<em>b</em>]selenophenes, benzofurans and indoles can also be prepared by this protocol. This reaction is convenient to perform at room temperature under simple conditions using air as the oxidant. Mechanistic studies revealed that the formation of α-thioalkyl radicals intermediate is crucial.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100119"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182241","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A radical hydrohaloalkylation of the ligand sphere of a chiral dehydroalanine Ni(II) complex: An asymmetric route to halogenated α-amino acid derivatives 手性脱氢丙氨酸镍(II)配合物配体球的自由基氢烷基化:卤化α-氨基酸衍生物的不对称途径
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2024-12-31 DOI: 10.1016/j.tchem.2024.100118
Nadezhda V. Stoletova , Alexander F. Smol'yakov , Andrey A. Tyutyunov , Victor I. Maleev , Vladimir A. Larionov
{"title":"A radical hydrohaloalkylation of the ligand sphere of a chiral dehydroalanine Ni(II) complex: An asymmetric route to halogenated α-amino acid derivatives","authors":"Nadezhda V. Stoletova ,&nbsp;Alexander F. Smol'yakov ,&nbsp;Andrey A. Tyutyunov ,&nbsp;Victor I. Maleev ,&nbsp;Vladimir A. Larionov","doi":"10.1016/j.tchem.2024.100118","DOIUrl":"10.1016/j.tchem.2024.100118","url":null,"abstract":"<div><div>An asymmetric synthetic protocol for the access to chiral artificial halogenated α-amino acid (α-AA) derivatives was elaborated through the radical functionalization of a double bond in the ligand sphere of a robust chiral dehydroalanine Belokon's Ni(II) complex by hydrohaloalkylation reaction. A 4-cyano-pyrydine/B<sub>2</sub>Pin<sub>2</sub> system promoted the <em>in situ</em> generation of radicals from halocarbons (including the hetero halogen atoms) for the subsequent coupling with the Ni(II) complex, providing the desired complexes with the yields in the range of 40–65%. The further post-modification of the side AA chain allowed to obtain the complexes with cyclopropane ring and to substitute the bromine atom on hydrogen one as well. Exemplary, two enantiopure α-AAs, including (<em>S</em>)-2-amino-4,4,4-trichlorobutanoic acid, were isolated by an acidic decomposition of the single diastereomeric Ni(II) complexes along with the recovery of the chiral auxiliary.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100118"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182240","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of spiro[4.4]nonane-containing functional organic molecules 合成含螺[4.4]壬烷的功能有机分子
Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-09-26 DOI: 10.1016/j.tchem.2024.100095
Zhuo Wang , Chunngai Hui , Hu Wang
{"title":"Synthesis of spiro[4.4]nonane-containing functional organic molecules","authors":"Zhuo Wang ,&nbsp;Chunngai Hui ,&nbsp;Hu Wang","doi":"10.1016/j.tchem.2024.100095","DOIUrl":"10.1016/j.tchem.2024.100095","url":null,"abstract":"<div><div>Spiro[4.4]nonane features are an important scaffold in many applications such as enantioenriched ligands, functional materials, natural products, and polymers. Excited by the prospect of the spiro[4.4]nonane scaffold, its structural intricacy still appears challenging in chemical synthesis. Many functional organic molecules possessing spiro[4.4]nonane scaffold(s) have recently been reported and synthesized. We provide a <em>Minireview</em> highlighting such advancements and discuss the future opportunities of spiro[4.4]nonane scaffolds in organic chemistry. Representative examples from 2019 to 2024 are discussed.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100095"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420265","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent advances in catalytic carbofluorination of unsaturated system via C–F bond reconstruction 通过 C-F 键重构催化不饱和体系羧基氟化的最新进展
Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-11-06 DOI: 10.1016/j.tchem.2024.100109
Yaxin Zeng, Xufei Yan, Ying Xia
{"title":"Recent advances in catalytic carbofluorination of unsaturated system via C–F bond reconstruction","authors":"Yaxin Zeng,&nbsp;Xufei Yan,&nbsp;Ying Xia","doi":"10.1016/j.tchem.2024.100109","DOIUrl":"10.1016/j.tchem.2024.100109","url":null,"abstract":"<div><div>The distinctive properties of the fluorine atom confer significant advantages to organofluorine compounds in pharmaceuticals, agrochemicals, and materials science. A particularly promising approach for synthesizing these compounds involves atom-economical carbofluorination reactions. These reactions involve the activation of a carbon-fluorine (C–F) bond, then facilitating the incorporation of both a carbon-based fragment and a fluorine atom into an unsaturated system. The capacity to reintegrate the fluorine atom from the starting material into the final product, known as fluoride recycling via C–F bond reconstruction, is advantageous in terms of both atom and step economy. This review highlights recent advancements in catalytic C–F bond reconstruction, encompassing the background, chemical transformations, reaction scope, synthetic applications, mechanisms, and future research directions.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100109"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142653833","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones 铜催化 1,5-二炔与苯并环丁烯酮的分子间正规 [4 + 1] 环化反应
Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-08-14 DOI: 10.1016/j.tchem.2024.100090
Jia-Cheng Li , Tian-Qi Hu , Zhou Xu , Bo Zhou , Long-Wu Ye
{"title":"Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones","authors":"Jia-Cheng Li ,&nbsp;Tian-Qi Hu ,&nbsp;Zhou Xu ,&nbsp;Bo Zhou ,&nbsp;Long-Wu Ye","doi":"10.1016/j.tchem.2024.100090","DOIUrl":"10.1016/j.tchem.2024.100090","url":null,"abstract":"<div><p>The one-carbon ring expansion of benzocyclobutenones is an efficient methodology for the assembly of cyclic ketones. However, hazardous reagents or noble metal catalysts are frequently required. Herein, we disclose a copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones, allowing the practical and atom-economical construction of diverse pyrryl 1-indanones in generally good yields under mild reaction conditions. This reaction represents an important advancement in the ring expansion of benzocyclobutenones <em>via</em> vinyl cation pathway.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100090"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000299/pdfft?md5=23f3b40c0b3b57810a312b754ccef9c1&pid=1-s2.0-S2666951X24000299-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141997210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Self-assembly via hydrogen bonding of bis(18-crown-6)-1,3-distyrylbenzene and [2 + 2] photocycloaddition: Stereoselective synthesis of [2.2]metacyclophanes and butterfly-type thermal isomerization 双(18-冠-6)-1,3-二苯乙烯通过氢键自组装和[2 + 2]光环加成:2.2]metacyclophanes 的立体选择性合成和蝶式热异构化
Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-08-18 DOI: 10.1016/j.tchem.2024.100091
Timofey P. Martyanov , Artem P. Vorozhtsov , Evgeny N. Ushakov , Nikita A. Slesarenko , Ilia V. Sulimenkov , Sergey P. Gromov
{"title":"Self-assembly via hydrogen bonding of bis(18-crown-6)-1,3-distyrylbenzene and [2 + 2] photocycloaddition: Stereoselective synthesis of [2.2]metacyclophanes and butterfly-type thermal isomerization","authors":"Timofey P. Martyanov ,&nbsp;Artem P. Vorozhtsov ,&nbsp;Evgeny N. Ushakov ,&nbsp;Nikita A. Slesarenko ,&nbsp;Ilia V. Sulimenkov ,&nbsp;Sergey P. Gromov","doi":"10.1016/j.tchem.2024.100091","DOIUrl":"10.1016/j.tchem.2024.100091","url":null,"abstract":"<div><p>The photochemistry of bis(18-crown-6)-containing 1,3-distyrylbenzene and its 2 : 2 bis-pseudo-sandwich complex with ethane-1,2-diammonium was studied. The UV irradiation of the supramolecular complex resulted in the formation of three geometric isomers of tetracrown-containing dicyclobutano[2.2]metacyclopane, differing in the orientation of the cyclobutane moieties, with the unsymmetrical isomer (&gt;50 %) predominating. The diammonium cations used as the template could be removed after photolysis by simple extraction, and the product was obtained in high yield (82 %). The <sup>1</sup>H NMR signals of a mixture of geometric isomers of [2.2]metacyclophane derivative were assigned resorting to quantum chemistry methods (DFT). The kinetic and thermodynamic parameters of thermal isomerization between the <em>endo</em>,<em>endo</em>- and <em>exo</em>,<em>exo</em>-isomers were measured. Tetracrown-containing dicyclobutano[2.2]metacyclophanes are homotetratopic ligands that contain four binding sites for metal and ammonium cations, which is of interest for the design of photo- and thermo-switchable supramolecular devices with a variable complex formation behavior and supramolecular machines owing to the butterfly-type thermal isomerization.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100091"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000305/pdfft?md5=bbc61009297f58bea762604b4ff7acfe&pid=1-s2.0-S2666951X24000305-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142098210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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