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Electrochemical synthesis of 2-amino-1,3,4-oxadiazoles via TBAI-mediated desulfurative cyclization of isothiocyanates and hydrazines tbai介导异硫氰酸酯和肼的脱硫环化电化学合成2-氨基-1,3,4-恶二唑
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-24 DOI: 10.1016/j.tet.2025.134746
Junwu Li , Rui Wang , Qing Huang , Wenxue Li , Zhenyu An , Yafeng Liu
{"title":"Electrochemical synthesis of 2-amino-1,3,4-oxadiazoles via TBAI-mediated desulfurative cyclization of isothiocyanates and hydrazines","authors":"Junwu Li ,&nbsp;Rui Wang ,&nbsp;Qing Huang ,&nbsp;Wenxue Li ,&nbsp;Zhenyu An ,&nbsp;Yafeng Liu","doi":"10.1016/j.tet.2025.134746","DOIUrl":"10.1016/j.tet.2025.134746","url":null,"abstract":"<div><div>Herein, we present an electrochemical approach for the synthesis of 2-amino-1,3,4-oxadiazoles from <em>N</em>-acyl hydrazides and isothiocyanates. Using TBAI as the electrolyte enables a mild oxidative cyclization without the need for stoichiometric oxidants. The reaction proceeds <em>via</em> the <em>in situ</em> generation of a thiosemicarbazide intermediate, and demonstrated by its broad substrate scope and good functional group compatibility.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134746"},"PeriodicalIF":2.1,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144147740","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
Visible light-induced environment-friendly cross-dehydrogenative coupling reaction of N-heterocycles with aldehyde 可见光诱导环境友好型n -杂环与醛的交叉脱氢偶联反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-24 DOI: 10.1016/j.tet.2025.134735
Divyani P. Patel, Vishwa K. Patel, Satish Kumar Singh
{"title":"Visible light-induced environment-friendly cross-dehydrogenative coupling reaction of N-heterocycles with aldehyde","authors":"Divyani P. Patel,&nbsp;Vishwa K. Patel,&nbsp;Satish Kumar Singh","doi":"10.1016/j.tet.2025.134735","DOIUrl":"10.1016/j.tet.2025.134735","url":null,"abstract":"<div><div>The development of efficient and sustainable methods for constructing carbon-carbon bonds is a pivotal challenge in modern green chemistry. Herein, we unveil a visible-light-driven oxidative cross-dehydrogenative coupling strategy between <em>N</em>-heterocycles and aldehydes using rose bengal as an organophotoredox catalyst under environmentally benign reaction conditions. This innovative green approach enables the direct acylation of <em>N</em>-heterocycles with various aldehydes, delivering high yields under mild reaction conditions at room temperature. Mechanistic studies demonstrate a radical pathway in which visible light activates a photocatalyst (rose bengal), leading to the generation of acyl radicals through single-electron transfer (SET). These radicals subsequently react with <em>N</em>-heterocycles to yield acylated products. This method is highly valuable for synthesizing diverse <em>N</em>-heterocyclic frameworks due to its mild reaction conditions, simple operation, and broad substrate scope. This research enhances photoredox catalysis and establishes a basis for more sustainable and adaptable synthetic methods.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134735"},"PeriodicalIF":2.1,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144135178","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
Rapid colorimetric recognition of tetrafluoroborate in water based on a phenol red derivative 基于酚红衍生物的水中四氟硼酸盐的快速比色识别
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-23 DOI: 10.1016/j.tet.2025.134745
Jiabin Lu , Qi Liu , Meipin Liu , Lanqin Tang , Lin Sun , Xinyu Song , Ruiyu Jiang , Lei Zhang
{"title":"Rapid colorimetric recognition of tetrafluoroborate in water based on a phenol red derivative","authors":"Jiabin Lu ,&nbsp;Qi Liu ,&nbsp;Meipin Liu ,&nbsp;Lanqin Tang ,&nbsp;Lin Sun ,&nbsp;Xinyu Song ,&nbsp;Ruiyu Jiang ,&nbsp;Lei Zhang","doi":"10.1016/j.tet.2025.134745","DOIUrl":"10.1016/j.tet.2025.134745","url":null,"abstract":"<div><div>Anion recognition in water by artificial receptors with high binding affinities remains challenging. Herein, we report a water-soluble colorimetric anion receptor synthesized via one-step aldehyde functionalization of phenol red (PS), characterized by NMR, MS, FTIR, and TGA. The modified receptor (MPS) exhibits solvent-, pH-, and anion-responsive chromism, contrasting with unmodified PS. MPS enables rapid BF<sub>4</sub><sup>−</sup> recognition in pure water, inducing a distinct red-to-yellow color change. UV–vis titration reveals a 1:1 binding stoichiometry with an ultrahigh affinity of 2.7 × 10<sup>6</sup> M<sup>−1</sup>, surpassing most reported receptors. MPS achieves a BF<sub>4</sub><sup>−</sup> detection limit of 10<sup>−5</sup> M and maintains selectivity against common anions and cations. This work provides a strategy for designing high-performance aqueous-phase anion sensors.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134745"},"PeriodicalIF":2.1,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144203283","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
Recent advances in photoredox/transition metal-catalyzed sulfonylation using sodium sulfinates 亚硫酸钠光氧化还原/过渡金属催化磺化研究进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-21 DOI: 10.1016/j.tet.2025.134733
Da-Liang Zhu , Jie Li , David J. Young , Yanqing Wang , Hong-Xi Li
{"title":"Recent advances in photoredox/transition metal-catalyzed sulfonylation using sodium sulfinates","authors":"Da-Liang Zhu ,&nbsp;Jie Li ,&nbsp;David J. Young ,&nbsp;Yanqing Wang ,&nbsp;Hong-Xi Li","doi":"10.1016/j.tet.2025.134733","DOIUrl":"10.1016/j.tet.2025.134733","url":null,"abstract":"<div><div>Sulfonylation employing sodium sulfinate salts as substrates and a combination of transition-metal and photoredox catalysis is a versatile synthetic tool for accessing structurally diverse sulfones under mild conditions. This review highlights recent advances in this methodology detailing the reaction mechanism, substrate scope, limitations and outlook.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134733"},"PeriodicalIF":2.1,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124268","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
The synthesis and evaluation of a series of novel fused rings based benzothiazole derivatives as potent Polθ inhibitors 一系列新型融合环基苯并噻唑衍生物的合成和评价
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-20 DOI: 10.1016/j.tet.2025.134734
Chao Kan , Chongxun Ge , Song Liu , Song Shi , Hu He , Weike Su
{"title":"The synthesis and evaluation of a series of novel fused rings based benzothiazole derivatives as potent Polθ inhibitors","authors":"Chao Kan ,&nbsp;Chongxun Ge ,&nbsp;Song Liu ,&nbsp;Song Shi ,&nbsp;Hu He ,&nbsp;Weike Su","doi":"10.1016/j.tet.2025.134734","DOIUrl":"10.1016/j.tet.2025.134734","url":null,"abstract":"<div><div>Polymerase theta (Polθ) is considered as a promising therapeutic target due to its function as an alternative DNA repair mechanism in Homologous Recombination (HR)-deficient cancer cells, and the potential for inducing synthetic lethality. The development of small molecule inhibitors that selectively bind to Polθ on DNA and overcome the resistance to PARP inhibitors (PARPi) significantly bolsters the innovative potential of this target in the field of precision oncology. In this study, we designed and synthesized a series of tetracyclic-fused benzothiazole derivatives. These novel compounds exhibit potent and selective inhibitory activity against the Polθ enzyme.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134734"},"PeriodicalIF":2.1,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144138302","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
Recent advances in catalytic transformations of ortho-alkynylnaphthols 正炔基萘酚催化转化研究进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-19 DOI: 10.1016/j.tet.2025.134726
Fatemeh Doraghi , Reza Hassanzadeh Dostkoh , Haniyeh Tavakoli , Bagher Larijani , Mohammad Mahdavi
{"title":"Recent advances in catalytic transformations of ortho-alkynylnaphthols","authors":"Fatemeh Doraghi ,&nbsp;Reza Hassanzadeh Dostkoh ,&nbsp;Haniyeh Tavakoli ,&nbsp;Bagher Larijani ,&nbsp;Mohammad Mahdavi","doi":"10.1016/j.tet.2025.134726","DOIUrl":"10.1016/j.tet.2025.134726","url":null,"abstract":"<div><div>Due to multiple reactive sites, <em>ortho</em>-alkynylnaphthols are extensively used in a diverse range of organic transformations. These precursors can be readily transformed into highly electrophilic vinylidene-quinone methide (VQM), vinyl carbocation, or vinyl radical intermediates towards the synthesis of a large family of auxiliary chiral organic compounds containing biaryls, aryl/heteroaryl and aryl/styrenes. The attractiveness of <em>ortho</em>-alkynylnaphthol from a synthetic point of view has led us to highlight the transformations of this valuable molecule in the presence of various catalytic methods, such as Lewis acidic, Brønsted acidic, Brønsted basic and metal catalytic systems.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"183 ","pages":"Article 134726"},"PeriodicalIF":2.1,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144116393","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
Tethered aza-Wacker cyclization reactions with unusual N-alkoxy carbamates 不寻常的n -烷氧基氨基甲酸酯系链aza-Wacker环化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-17 DOI: 10.1016/j.tet.2025.134730
Appasaheb K. Nirpal , Dnyaneshwar A. Gorve , Raju Silver , Steven P. Kelley , Shyam Sathyamoorthi
{"title":"Tethered aza-Wacker cyclization reactions with unusual N-alkoxy carbamates","authors":"Appasaheb K. Nirpal ,&nbsp;Dnyaneshwar A. Gorve ,&nbsp;Raju Silver ,&nbsp;Steven P. Kelley ,&nbsp;Shyam Sathyamoorthi","doi":"10.1016/j.tet.2025.134730","DOIUrl":"10.1016/j.tet.2025.134730","url":null,"abstract":"<div><div>Substrates with <em>N</em>-alkoxy carbamate “heads” and olefin “tails” can be productively cyclized into 1,3-oxazinan-2-one products bearing pendant alkenes. Our reaction protocol is operationally simple and involves heating the substrate with a mixture of Pd (II) and Cu (II) salts in CH<sub>3</sub>CN under 1 atm of O<sub>2</sub>. We hypothesize that an <em>aza</em>-Wacker mechanism is operative, based on prior art and our own experience with this reaction class. An array of substrates is compatible, and the heterocyclic products are amenable to further transformations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"183 ","pages":"Article 134730"},"PeriodicalIF":2.1,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144099729","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
Recyclable, high adhesive strength small molecule rosin-based epoxy resin with AIE properties 可回收，高粘接强度的小分子松香基环氧树脂，具有AIE性能
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-17 DOI: 10.1016/j.tet.2025.134732
Qian Wu , Peng Yang , Zhijun Ke , Hanwen Wang , Zehua Zhang , Boyi Zhang , Shenglin Li , Xiaoping Rao
{"title":"Recyclable, high adhesive strength small molecule rosin-based epoxy resin with AIE properties","authors":"Qian Wu ,&nbsp;Peng Yang ,&nbsp;Zhijun Ke ,&nbsp;Hanwen Wang ,&nbsp;Zehua Zhang ,&nbsp;Boyi Zhang ,&nbsp;Shenglin Li ,&nbsp;Xiaoping Rao","doi":"10.1016/j.tet.2025.134732","DOIUrl":"10.1016/j.tet.2025.134732","url":null,"abstract":"<div><div>The utilize of epoxy resins always necessitates the aid of petroleum-based curing agents to facilitate cross-linking and engender an irreversible tridimensional network structure. However, this characteristic, in turn, imposes the constraint of recyclability in their applications and hinders sustainable development. Creating a durable and repeatedly useable epoxy resin adhesive that can withstand mild bonding conditions lingers a significant challenge. In this work, a novel rosin-based epoxy resin (HAR-EP<sub>x</sub>) was successfully prepared from hydrogenated acrylic rosin (HAR) and epoxy resin (EP<sub>x</sub>) based on the structure of the hydrogenated phenanthrene ring with large steric hindrance and low cross-linking density. The HAR-EP<sub>x</sub> prepared in this study exhibits several remarkable properties, such as outstanding heat resistance (T<sub>d</sub> = 354 °C), exceptional UV–visible light transmittance. HAR-EP<sub>x</sub> can be applied to adhesives without curing agents, and was characterized by mild bonding conditions (85 °C, 1.5 min), high mechanical properties (adhesion strength up to 4.306 MPa), and excellent reusability that retains over 80 % bonding strength even after undergoing 6 cycles. Moreover, it exhibits an intriguing characteristic, that is, it emits intrinsic cyan-green fluorescence when subjected to UV excitation, attributed to aggregation-induced emission (AIE).</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"183 ","pages":"Article 134732"},"PeriodicalIF":2.1,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144088638","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 synthesis of benzo[d]thiazoles and chalcogenol esters through reduction of disulfides and diselenides promoted by enamine-based organic electron donors 胺基有机电子给体通过还原二硫化物和二硒化物温和合成苯并[d]噻唑和硫酚酯
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-17 DOI: 10.1016/j.tet.2025.134729
Anne Roly Obah Kosso, Julie Broggi, Patrice Vanelle, Sébastien Redon
{"title":"Mild synthesis of benzo[d]thiazoles and chalcogenol esters through reduction of disulfides and diselenides promoted by enamine-based organic electron donors","authors":"Anne Roly Obah Kosso,&nbsp;Julie Broggi,&nbsp;Patrice Vanelle,&nbsp;Sébastien Redon","doi":"10.1016/j.tet.2025.134729","DOIUrl":"10.1016/j.tet.2025.134729","url":null,"abstract":"<div><div>The reduction of disulfide bridges (S–S) has attracted growing attention, as they serve as stable and non-odoriferous thiol precursors. To prove the ability of enamine-based organic electron donors (OEDs) in original S–S bond cleavage reactivities, we undertook here the synthesis of benzothiazoles through OED-promoted reduction of disulfide bridges. The metal-free and mild conditions enabled the synthesis of benzothiazoles with a wide tolerance to different functional groups and good yields. Synthesis of thio- or seleno-benzoates from the reduction of disulfide or diselenide was also obtained.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"183 ","pages":"Article 134729"},"PeriodicalIF":2.1,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144099730","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
Preparation of 3,5-bis(methylidene)-2,6-heptanedione and its application as a Michael acceptor 3,5-二（亚甲基）-2,6-庚二酮的制备及其作为迈克尔受体的应用
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-17 DOI: 10.1016/j.tet.2025.134731
Xixuan Zhao, Leyi Chang, Zilin Fang, Longchen Zhang, Shenghao Che, Sen Liang, Yongguo Liu, Baoguo Sun, Hongyu Tian, Ning Li
{"title":"Preparation of 3,5-bis(methylidene)-2,6-heptanedione and its application as a Michael acceptor","authors":"Xixuan Zhao,&nbsp;Leyi Chang,&nbsp;Zilin Fang,&nbsp;Longchen Zhang,&nbsp;Shenghao Che,&nbsp;Sen Liang,&nbsp;Yongguo Liu,&nbsp;Baoguo Sun,&nbsp;Hongyu Tian,&nbsp;Ning Li","doi":"10.1016/j.tet.2025.134731","DOIUrl":"10.1016/j.tet.2025.134731","url":null,"abstract":"<div><div>A good Michael acceptor, 3,5-bis(methylidene)-2,6-heptanedione, was obtained in 31 % yield by the reaction of 2,4-pentanedione with formaldehyde derived from the decomposition of DMSO. Various primary amines underwent Michael addition with 3,5-bis(methylidene)-2,6-heptanedione, followed by intramolecular aldol condensation in a one-pot reaction to yield bicyclic products, <em>N</em>-substituted-8-methyl-3-azabicyclo[3.3.1]non-7-en-6-ones, with yields ranging from 32 % to 64 %. Reactions with sterically hindered amines resulted in bicyclic products with yields lower than 10 %, and reactions with aromatic amines did not yield the bicyclic products. The reaction of benzylthiol as a nucleophile gave 4,6-bis(benzylthiomethyl)-3-methyl-cyclohex-2-en-1-one with a yield of 47 %.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"183 ","pages":"Article 134731"},"PeriodicalIF":2.1,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144099728","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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