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t-BuOLi-promoted Knoevenagel condensation: An efficient approach for synthesizing Arylid-BOX t- buoli促进Knoevenagel缩合：一种合成芳基酰胺- box的有效方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-18 DOI: 10.1016/j.tetlet.2025.155706
Run He, Zilong Zhang, Yuxiang Zhou, Li Zeng, Lou Shi, Deqiang Liang
{"title":"t-BuOLi-promoted Knoevenagel condensation: An efficient approach for synthesizing Arylid-BOX","authors":"Run He,&nbsp;Zilong Zhang,&nbsp;Yuxiang Zhou,&nbsp;Li Zeng,&nbsp;Lou Shi,&nbsp;Deqiang Liang","doi":"10.1016/j.tetlet.2025.155706","DOIUrl":"10.1016/j.tetlet.2025.155706","url":null,"abstract":"<div><div>A <em>t</em>-BuOLi-promoted Knoevenagel condensation is reported, offering a straightforward method for the rapid construction of Arylid-BOX. This late-stage functionalization method of unsubstituted BOX ligands enables the rapid synthesis of a wide range of Arylid-BOX compounds. We speculate that the relatively small atomic radius of lithium ions contributes to the high yields of this reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155706"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Mercaptan-free approach to the synthesis of Ethiprole, an insecticide 无硫醇合成杀虫剂乙虫乐的方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-18 DOI: 10.1016/j.tetlet.2025.155713
Rachel Gundamalla , P. Naveen Reddy , RajashakerBantu , B.V. Subba Reddy
{"title":"Mercaptan-free approach to the synthesis of Ethiprole, an insecticide","authors":"Rachel Gundamalla ,&nbsp;P. Naveen Reddy ,&nbsp;RajashakerBantu ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tetlet.2025.155713","DOIUrl":"10.1016/j.tetlet.2025.155713","url":null,"abstract":"<div><div>An efficient and practical method has been developed for the synthesis of a second-generation insecticide, ethiprole. The key step involved in this approach is the thiocynation of pyrazole ring at the 4th position, which was achieved using bromine and potassium thiocyanate in methanol. Another important step involves the one-pot conversion of thiocyanate into ethyl sulfide using ethyl bromide in the presence of a base. Each step in this synthesis was performed efficiently on a gram scale to produce high-quality product. This new synthetic strategy is simple, convenient and scalable.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155713"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329791","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Total syntheses of anticancer Abietane Diterpenoids, (±)-Royleanone and (±)-Inuroyleanol via Lewis acid catalyzed Hydroarylation 路易斯酸催化氢化芳基化合成抗癌阿比烷二萜（±）-罗伊精酮和（±）-尿精醇
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-18 DOI: 10.1016/j.tetlet.2025.155715
Badrinath N. Kakde , Suman Noskar , Saikat Bag , Alakesh Bisai
{"title":"Total syntheses of anticancer Abietane Diterpenoids, (±)-Royleanone and (±)-Inuroyleanol via Lewis acid catalyzed Hydroarylation","authors":"Badrinath N. Kakde ,&nbsp;Suman Noskar ,&nbsp;Saikat Bag ,&nbsp;Alakesh Bisai","doi":"10.1016/j.tetlet.2025.155715","DOIUrl":"10.1016/j.tetlet.2025.155715","url":null,"abstract":"<div><div>Herein we report a Lewis acid-catalyzed intramolecular hydroarylation strategy enabling an efficient synthesis of [6,6,6]-fused abietane diterpenoids sharing a trans-decalin motif. Using bismuth(III) triflate as an efficient metal triflate, the key intermediates were prepared in high yields, facilitating concise total syntheses of royleanone (<strong>1a</strong>) and inuroyleanone (<strong>1c</strong>), showcasing a scalable approach to complex natural product frameworks.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155715"},"PeriodicalIF":1.5,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329790","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
An efficient synthesis of Indolo[3,2-c]coumarins by Pd-catalyzed intramolecular CH carbonylation pd催化分子内CH羰基化高效合成吲哚[3,2-c]香豆素
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-17 DOI: 10.1016/j.tetlet.2025.155716
Hai-Bing Long, Xue-Hua Huang, Da-Xian You, Ye Liang, Jin-Bao Peng, Jia-Lei Yan, Ai-Jun Ma
{"title":"An efficient synthesis of Indolo[3,2-c]coumarins by Pd-catalyzed intramolecular CH carbonylation","authors":"Hai-Bing Long,&nbsp;Xue-Hua Huang,&nbsp;Da-Xian You,&nbsp;Ye Liang,&nbsp;Jin-Bao Peng,&nbsp;Jia-Lei Yan,&nbsp;Ai-Jun Ma","doi":"10.1016/j.tetlet.2025.155716","DOIUrl":"10.1016/j.tetlet.2025.155716","url":null,"abstract":"<div><div>Indolo[3,2-<em>c</em>]coumarins, characterized by their distinctive fused heterocyclic architecture, demonstrate significant biological activities in natural settings. In this study, we report a Pd-catalyzed intramolecular C<img>H carbonylation methodology for the synthesis of indolo[3,2-<em>c</em>]coumarins, and provide a straightforward approach for the total synthesis of natural product derivative and bioactive molecule of this class. This novel methodology provides a versatile platform for the comprehensive synthesis of indolo[3,2-<em>c</em>]coumarins.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155716"},"PeriodicalIF":1.5,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144338692","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Highly sensitive turn-on fluorescent probe for the specific detection of cadaverine in shrimp 对虾尸体碱特异检测的高灵敏度开启荧光探针
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-16 DOI: 10.1016/j.tetlet.2025.155714
Pei Liu , Wei Du , Yu-An Feng , Yu-Bin Su , Ya-Wen Wang , Jian Xiao , Yu Peng
{"title":"Highly sensitive turn-on fluorescent probe for the specific detection of cadaverine in shrimp","authors":"Pei Liu ,&nbsp;Wei Du ,&nbsp;Yu-An Feng ,&nbsp;Yu-Bin Su ,&nbsp;Ya-Wen Wang ,&nbsp;Jian Xiao ,&nbsp;Yu Peng","doi":"10.1016/j.tetlet.2025.155714","DOIUrl":"10.1016/j.tetlet.2025.155714","url":null,"abstract":"<div><div>An organic small-molecule fluorescent probe <strong>SWJT-36</strong> with an isophorone backbone for the specific detection of cadaverine (Cad), a shrimp spoilage marker, was developed. After the reaction the solution exhibited a distinct color change from pale yellow to deep amber under visible light irradiation, accompanied by intense red fluorescence emission. Particularly, <strong>SWJT-36</strong> exhibited high selectivity, low detection limit (2.655 μM), and fast response (t<sub>1/2</sub> = 13.8 min) for Cad. The reaction mechanism of <strong>SWJT-36</strong> and Cad was determined by mass spectrometry. And <strong>SWJT-36</strong> could be made into portable test strips that could detect Cad, thereby detecting the freshness of shrimp.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155714"},"PeriodicalIF":1.5,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Catalytic reductive annulation reactions of alkenes using dihaloalkanes 二卤代烷烃催化还原环化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-16 DOI: 10.1016/j.tetlet.2025.155705
Sayan Roy , Divya Garg , Christopher Uyeda
{"title":"Catalytic reductive annulation reactions of alkenes using dihaloalkanes","authors":"Sayan Roy ,&nbsp;Divya Garg ,&nbsp;Christopher Uyeda","doi":"10.1016/j.tetlet.2025.155705","DOIUrl":"10.1016/j.tetlet.2025.155705","url":null,"abstract":"<div><div>A nickel catalyst promotes the reductive annulation of alkenes using 1,3-dihalopropanes to provide substituted cyclopentanes. Mechanistic studies indicate that activation of the dihaloalkane occurs by a halogen-atom abstraction mechanism to generate a carbon-centered radical. Overall, the method provides direct access to saturated ring-systems from simple acyclic reaction partners.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155705"},"PeriodicalIF":1.5,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144290704","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Iridium-catalyzed ester-directed oxidative coupling of aromatic esters and alkenes 铱催化芳香酯和烯烃的酯化氧化偶联
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-14 DOI: 10.1016/j.tetlet.2025.155707
Elumalai Kumaran, Zhen Xuan Wong, Weng Kee Leong
{"title":"Iridium-catalyzed ester-directed oxidative coupling of aromatic esters and alkenes","authors":"Elumalai Kumaran,&nbsp;Zhen Xuan Wong,&nbsp;Weng Kee Leong","doi":"10.1016/j.tetlet.2025.155707","DOIUrl":"10.1016/j.tetlet.2025.155707","url":null,"abstract":"<div><div>The directing group-assisted, transition metal-catalyzed oxidative coupling of arenes with alkenes is a powerful tool for synthesizing functionalized alkenes. In this work, we report the iridium catalyzed oxidative coupling of aromatic esters with alkenes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155707"},"PeriodicalIF":1.5,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307135","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Stereoselective synthesis, optical characterization, DFT, and metal ion detection of tetra p-tert-butylthiacalix[4]arene derivatives containing amide and thiamide fragments at lower rim 立体选择合成，光学表征，DFT，和金属离子检测四对叔丁基噻唑烷衍生物含酰胺和硫酰胺片段的下边缘
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-14 DOI: 10.1016/j.tetlet.2025.155709
Mohamed Sharaf , Amr H. Moustafa , Mounier A.A. Mohamed , Moumen S. Kamel , Aly Abdou , Omran A. Omran
{"title":"Stereoselective synthesis, optical characterization, DFT, and metal ion detection of tetra p-tert-butylthiacalix[4]arene derivatives containing amide and thiamide fragments at lower rim","authors":"Mohamed Sharaf ,&nbsp;Amr H. Moustafa ,&nbsp;Mounier A.A. Mohamed ,&nbsp;Moumen S. Kamel ,&nbsp;Aly Abdou ,&nbsp;Omran A. Omran","doi":"10.1016/j.tetlet.2025.155709","DOIUrl":"10.1016/j.tetlet.2025.155709","url":null,"abstract":"<div><div><em>P</em>-tolylacetamide and <em>p</em>-tolylthioacetamide fragments are present in new <em>p-tert</em>-butylthiacalix[4]arenes at lower rims. <em>P-tert</em>-butylthiacalix[4]arene<strong>1</strong>reacted with 2-chloro (<em>p</em>-tolyl)acetamide to produce acetamide derivatives of thiacalixarene<strong>2–3</strong>, which are then thionated with Lawesson's reagent to produce thiacetamidethiacalixarenes derivatives <strong>4–5</strong>. FT-IR, NMR, metal ion detection, and the optical absorption spectrum characteristics of the novel thiacalixarenes derivative have all been used to analyze their structures. Density Functional Theory calculations revealed critical insights into the electronic, structural, and reactive properties of thiacalixarene derivatives (<strong>2–5</strong>). Compound <strong>2</strong> exhibited the highest nucleophilicity, lowest energy gap, and greatest reactivity towards metal uptake, underscoring its suitability for coordination chemistry. Computational analyses using the B3lyp/6-311++G** method matched well with experimental data, confirming the theoretical models. The IR spectra showed good agreement between experimental and theoretical results. Molecule electrostatic potential mapping highlighted possible sites for electrophilic interactions and stable metal-ligand bonding.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155709"},"PeriodicalIF":1.5,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144279728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Catalytic asymmetric approach to floral odorant, (+)- and (−)-Florhydral （+）-和(−)-花水合醛的催化不对称研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-11 DOI: 10.1016/j.tetlet.2025.155688
Debabrata Mondal , Dhruvilkumar Sureshkumar Patel , Vishnumaya Bisai
{"title":"Catalytic asymmetric approach to floral odorant, (+)- and (−)-Florhydral","authors":"Debabrata Mondal ,&nbsp;Dhruvilkumar Sureshkumar Patel ,&nbsp;Vishnumaya Bisai","doi":"10.1016/j.tetlet.2025.155688","DOIUrl":"10.1016/j.tetlet.2025.155688","url":null,"abstract":"<div><div>Catalytic asymmetric total synthesis of either enantiomer of floral odorant, i.e. (+)-florhydral® (<strong>1a</strong>) and (−)-florhydral® (<em>ent</em>-<strong>1a</strong>) has been achieved via a key catalytic asymmetric 3-isopropyl benzene boronic acid addition onto ethyl crotonate. Thus, an efficient two-step approach to both enantiomers of florhydral has been shown using 2 mol% Rh-(<em>S</em>)-BINAP (<strong>L1</strong>) as catalyst to achieve the product with a stereogenic center at the pseudo-benzylic position (up to 90 % ee).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155688"},"PeriodicalIF":1.5,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144255222","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Streptavidin binding stoichiometry of biotinylated silicon phthalocyanines: impact of axial ligands 生物素化硅酞菁链亲和素结合化学计量学：轴向配体的影响
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-11 DOI: 10.1016/j.tetlet.2025.155711
Takahiko Matsushita , Kanna Saito , Kengo Inagaki , Tetsuo Koyama , Ken Hatano , Koji Matsuoka
{"title":"Streptavidin binding stoichiometry of biotinylated silicon phthalocyanines: impact of axial ligands","authors":"Takahiko Matsushita ,&nbsp;Kanna Saito ,&nbsp;Kengo Inagaki ,&nbsp;Tetsuo Koyama ,&nbsp;Ken Hatano ,&nbsp;Koji Matsuoka","doi":"10.1016/j.tetlet.2025.155711","DOIUrl":"10.1016/j.tetlet.2025.155711","url":null,"abstract":"<div><div>Biotinylated silicon phthalocyanines (SiPcs) represent promising platforms for targeted molecular systems that engage streptavidin through high-affinity biotin–protein interactions. In this study, two SiPc derivatives were synthesized with biotin appended via distinct axial ligands. Although both compounds exhibited similar optical properties in dimethyl sulfoxide, their binding behavior with streptavidin differed markedly. A competitive displacement assay using 4′-hydroxyazobenzene-2-carboxylic acid revealed that compound <strong>1</strong> occupied approximately 3.5 binding pockets per streptavidin tetramer, whereas compound <strong>2</strong> showed negligible displacement even at high concentrations. SDS-PAGE analysis confirmed that the streptavidin tetramer remained intact in the presence of compound <strong>1</strong>, ruling out tetramer dissociation as a cause of sub-stoichiometric binding. These findings indicate that steric hindrance or limited spatial accessibility of the biotin moiety, possibly compounded by aggregation in aqueous media, critically impacts functional binding. This study demonstrates that the architecture of axial ligands affects the effective presentation of biotin on SiPc scaffolds and informs the design of supramolecular probes and photofunctional systems responsive to biological targets.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155711"},"PeriodicalIF":1.5,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144289195","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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