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Ir-catalyzed distal branch- and enantioselective hydroarylation of internal alkenes using acetanilides via chain-walking and CH activation 通过链走和CH活化，用乙酰苯胺催化远端分支和对映选择性内烯烃氢化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-10 DOI: 10.1016/j.tetlet.2025.155823
Mizuki Kadota, King Hung Nigel Tang, Takanori Shibata
{"title":"Ir-catalyzed distal branch- and enantioselective hydroarylation of internal alkenes using acetanilides via chain-walking and CH activation","authors":"Mizuki Kadota,&nbsp;King Hung Nigel Tang,&nbsp;Takanori Shibata","doi":"10.1016/j.tetlet.2025.155823","DOIUrl":"10.1016/j.tetlet.2025.155823","url":null,"abstract":"<div><div>This study presents the iridium-catalyzed branch- and enantioselective C<img>H alkylation of acetanilides with internal alkenes via chain-walking. This report addresses a key challenge in the selective C<img>C bond formation by using a newly developed electron-deficient TADDOL-based chiral ligand and we achieved an optimal balance between yield and enantiomeric ratio (up to 91:9 er). The use of 1.5 equivalent amounts of [Ir(cod)<sub>2</sub>]NTf<sub>2</sub> relative to chiral ligands significantly improved the yields along with perfect regioselectivity and good enantioselectivity. The substrate scope demonstrated the broad applicability of the method across various acetanilide and alkene derivatives, including functionalized arenes and alkenes bearing aryl or aliphatic substituents.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155823"},"PeriodicalIF":1.5,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145157010","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
Tautomerism, Z/E isomerization, and H-bonding in the amino and N-hetaryl derivatives of carbonyl compounds 羰基化合物的氨基和n -乙基衍生物中的互变异构、Z/E异构和h键
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-07 DOI: 10.1016/j.tetlet.2025.155821
Bagrat A. Shainyan , Mark V. Sigalov
{"title":"Tautomerism, Z/E isomerization, and H-bonding in the amino and N-hetaryl derivatives of carbonyl compounds","authors":"Bagrat A. Shainyan ,&nbsp;Mark V. Sigalov","doi":"10.1016/j.tetlet.2025.155821","DOIUrl":"10.1016/j.tetlet.2025.155821","url":null,"abstract":"<div><div>In the present review, two types of compounds capable of tautomerization with proton transfer between N and O atoms, isomerization by rotation about the C<img>C or C<img>N bonds, and hydrogen bonding in specific isomers are analyzed, focusing on the last two decades. The first type is enaminones attracting a growing interest as synthetic precursors of heterocycles, or, structurally, as push-pull ethylenes. This reduces the barrier to rotation around the double bond, and increases the barrier to rotation around the adjacent single bond. Another type of compounds also capable of tautomerism, conformational and rotational equilibrium, and the hydrogen bonding, is keto- or diketoenols with aromatic N-heterocycles at the C<img>C bond which have been investigated mainly by our research groups. Overall, the review summarizes recent advances in studying <em>E/Z</em> isomerization, tautomerism, H-bonding in enaminones and ketoenols, and relationship between these phenomena.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155821"},"PeriodicalIF":1.5,"publicationDate":"2025-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145026964","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
Novel metabolites from Pterocarpus marsupium: Structural characterization and biological relevance 有袋翼龙的新代谢物：结构表征和生物学相关性
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-05 DOI: 10.1016/j.tetlet.2025.155820
Kailas Arjun Chavan , Omkar A. Sonawane , Rohan D. Erande
{"title":"Novel metabolites from Pterocarpus marsupium: Structural characterization and biological relevance","authors":"Kailas Arjun Chavan ,&nbsp;Omkar A. Sonawane ,&nbsp;Rohan D. Erande","doi":"10.1016/j.tetlet.2025.155820","DOIUrl":"10.1016/j.tetlet.2025.155820","url":null,"abstract":"<div><div>Aiming to find novel natural products along with establishing a simple isolation process, here we described the efficient isolation of pterostilbene along with three unreported compounds – di-pterostilbene; 3,5-dimethoxybenzyl alcohol; and 5,5′-(oxybis(methylene))bis(1,3-dimethoxybenzene) from the heartwood of <em>P. marsupium via</em> a simple silica-gel flash column chromatography. A comprehensive structural elucidation of all the isolated compounds was done using spectroscopic techniques such as <sup>1</sup>H NMR, <sup>13</sup>C NMR, <sup>13</sup>C-DEPT135, <sup>1</sup>H–<sup>1</sup>H COSY, FT-IR and HRMS. Furthermore, <em>in silico</em> molecular docking studies of newly isolated molecules reveal to exhibit strong binding affinities towards antidiabetic and anticancer targets involved in glucose homeostasis, insulin signalling, and tumor progression. Additionally, <em>in vitro</em> cytotoxicity evaluation against A549 lung carcinoma cells revealed antiproliferative activity, which makes them promising therapeutic agents along with emerging lead scaffolds for antidiabetic and anticancer drug development.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155820"},"PeriodicalIF":1.5,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145019782","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
Deprotection of N-Allyloxycarbonyl groups using the NiCl2/NaBH4 system NiCl2/NaBH4体系对n -烯丙氧基羰基的脱保护
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-04 DOI: 10.1016/j.tetlet.2025.155818
Xinxin Yuan , Qianding Zeng , Liyuan Luo , Yuanhao Chen , Jie Gu , Xinyu Zhu , Wenjun Jin , Jiangmeng Ren , Bu-Bing Zeng
{"title":"Deprotection of N-Allyloxycarbonyl groups using the NiCl2/NaBH4 system","authors":"Xinxin Yuan ,&nbsp;Qianding Zeng ,&nbsp;Liyuan Luo ,&nbsp;Yuanhao Chen ,&nbsp;Jie Gu ,&nbsp;Xinyu Zhu ,&nbsp;Wenjun Jin ,&nbsp;Jiangmeng Ren ,&nbsp;Bu-Bing Zeng","doi":"10.1016/j.tetlet.2025.155818","DOIUrl":"10.1016/j.tetlet.2025.155818","url":null,"abstract":"<div><div>Herein, we developed a new method for the deprotection of <em>N</em>-allyloxycarbonyl (Alloc) using a NiCl₂/NaBH₄ system to provide the parent amino compounds with good to excellent yields. Notably, this practical protocol exhibits excellent compatibility with various <em>N</em>-alloc protected amines with different functional groups that derived from multi-substituted anilines, heteroaromatic and aliphatic amines or even some secondary amines. The mechanism of the reaction is also demonstrated.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155818"},"PeriodicalIF":1.5,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145026850","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
Diastereoselective synthesis of 3-substituted-3-hydroxy oxindoles from atropisomeric N-aryl isatin bearing an ortho-dimethylamino group 含邻二甲胺基的阿托罗二聚体n -芳基isatin非对映选择性合成3-取代-3-羟基氧吲哚
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-04 DOI: 10.1016/j.tetlet.2025.155817
Seiryu Tabata , Yuuya Kawasaki , Kazunobu Igawa , Katsuhiko Tomooka , Atsuo Nakazaki
{"title":"Diastereoselective synthesis of 3-substituted-3-hydroxy oxindoles from atropisomeric N-aryl isatin bearing an ortho-dimethylamino group","authors":"Seiryu Tabata ,&nbsp;Yuuya Kawasaki ,&nbsp;Kazunobu Igawa ,&nbsp;Katsuhiko Tomooka ,&nbsp;Atsuo Nakazaki","doi":"10.1016/j.tetlet.2025.155817","DOIUrl":"10.1016/j.tetlet.2025.155817","url":null,"abstract":"<div><div>3-Substituted-3-hydroxy oxindoles were synthesized via diastereoselective nucleophilic additions to an axially chiral racemic <em>N</em>-aryl isatin bearing an <em>ortho</em>-dimethylamino group on a <em>p</em>-(benzyloxy)aryl moiety. A switch in diastereoselectivity was observed (up to <em>anti</em>:<em>syn</em> = 29:71 to 74:26) depending on the organometallic reagent (RLi or RMgX). The <em>p</em>-(benzyloxy)aryl moiety was readily removed via a mild two-step sequence to afford N<img>H oxindole.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155817"},"PeriodicalIF":1.5,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145019783","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
Synthesis of phenazine-1,6-diyldimethanol, a natural product from Brevibacteria 短毛杆菌天然产物非那嗪-1,6-二基二甲醇的合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-02 DOI: 10.1016/j.tetlet.2025.155802
Ramsha Iftikhar , Mohan Bhadbhade , Ruoming Tian , Giancarlo Pascali , Roger Read , Luke Hunter
{"title":"Synthesis of phenazine-1,6-diyldimethanol, a natural product from Brevibacteria","authors":"Ramsha Iftikhar ,&nbsp;Mohan Bhadbhade ,&nbsp;Ruoming Tian ,&nbsp;Giancarlo Pascali ,&nbsp;Roger Read ,&nbsp;Luke Hunter","doi":"10.1016/j.tetlet.2025.155802","DOIUrl":"10.1016/j.tetlet.2025.155802","url":null,"abstract":"<div><div>A concise total synthesis of the C2-symmetric marine alkaloid, phenazine-1,6-diyldimethanol, is reported. X-ray crystal structures for three phenazine derivatives are presented, and a simple and general NMR-based method for distinguishing 1,6- from 1,9-disubstituted phenazines is described.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155802"},"PeriodicalIF":1.5,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144933078","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
Triterpenoid alkaloids from Buxus bodinieri and their bioactivities 黄杨中的三萜生物碱及其生物活性研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-02 DOI: 10.1016/j.tetlet.2025.155815
Hong-Jing Zha , Chun-Xia Chen , Xing Sun , Shi-Ying Yuan
{"title":"Triterpenoid alkaloids from Buxus bodinieri and their bioactivities","authors":"Hong-Jing Zha ,&nbsp;Chun-Xia Chen ,&nbsp;Xing Sun ,&nbsp;Shi-Ying Yuan","doi":"10.1016/j.tetlet.2025.155815","DOIUrl":"10.1016/j.tetlet.2025.155815","url":null,"abstract":"<div><div>Phytochemical investigation of a methanol extract of the twigs and leaves of <em>Buxus bodinieri</em> led to the isolation of four new triterpenoid alkaloids (<strong>1</strong>–<strong>4</strong>) and five known analogues (<strong>5</strong>–<strong>9</strong>). Their structures were determined by extensive analyses of their spectroscopic data and corroborated by the single-crystal X-ray diffraction. In LPS-induced RAW264.7 cells model, compounds <strong>1</strong> and <strong>2</strong> displayed the most potent anti-inflammatory effects, with IC<sub>50</sub> values of 7.5 and 6.1 μM, respectively. Compounds <strong>2</strong> and <strong>6</strong> also exhibited significant cytotoxic activity against HT-29 cell line (IC50 of 6.4 and 10.2 μM), representing 2.9-fold and 1.8-fold greater potency than the positive control cisplatin (IC<sub>50</sub> = 18.6 μM), respectively.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155815"},"PeriodicalIF":1.5,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145010359","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
AgSCF3-mediated direct Trifluoromethylthiolation of alkynyl iodides for aryl and alkyl ethynyl trifluoromethyl Sulfides agscf3介导的炔基碘化物直接三氟甲基硫化反应制备芳基和烷基乙基三氟甲基硫化物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-09-01 DOI: 10.1016/j.tetlet.2025.155816
Jianquan Hong, Qiang Wang, Chunxiang Li, Shengying Gu, Jie Wang, Xifei Chen, Chongbin Wei, Xinxin Gong, Wenqi Li, Changge Zheng
{"title":"AgSCF3-mediated direct Trifluoromethylthiolation of alkynyl iodides for aryl and alkyl ethynyl trifluoromethyl Sulfides","authors":"Jianquan Hong,&nbsp;Qiang Wang,&nbsp;Chunxiang Li,&nbsp;Shengying Gu,&nbsp;Jie Wang,&nbsp;Xifei Chen,&nbsp;Chongbin Wei,&nbsp;Xinxin Gong,&nbsp;Wenqi Li,&nbsp;Changge Zheng","doi":"10.1016/j.tetlet.2025.155816","DOIUrl":"10.1016/j.tetlet.2025.155816","url":null,"abstract":"<div><div>A practical synthetic method for the ethynyl trifluoromethyl sulfides through AgSCF<sub>3</sub>-mediated direct trifluoromethylthiolation has been developed. The reaction of the alkynyl iodides by CuI with 4,4′-di-<em>tert</em>-butyl-2,2′-bipyridine is performed under mild reaction conditions. This transformation efficiently affords aryl or alkyl acetenyl trifluoromethyl sulfides with good reaction yields, broad substrate scope, excellent compatibility and operational simplicity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155816"},"PeriodicalIF":1.5,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144988834","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
Electrosynthesis of quinones, a brief overview 醌类化合物的电合成综述
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-30 DOI: 10.1016/j.tetlet.2025.155801
Luis A. Segura-Quezada , Melissa Tapia-Juárez , Miriam P. Barrera-Nava , Luis Chacón-García , César R. Solorio-Alvarado
{"title":"Electrosynthesis of quinones, a brief overview","authors":"Luis A. Segura-Quezada ,&nbsp;Melissa Tapia-Juárez ,&nbsp;Miriam P. Barrera-Nava ,&nbsp;Luis Chacón-García ,&nbsp;César R. Solorio-Alvarado","doi":"10.1016/j.tetlet.2025.155801","DOIUrl":"10.1016/j.tetlet.2025.155801","url":null,"abstract":"<div><div>Quinones are essential compounds in organic synthesis due to their versatility and diverse range of applications in areas such as drug design, material science, and catalysis. Historically, quinone compounds preparation has attracted significant interest, with electrochemical methods being a notable approach among the available techniques. With a long-standing history, organic electrosynthesis represents a renewed strategy. It offers sustainability, as it does not demand the use of potential oxidants or reductants, thereby reducing the potential for negative environmental impacts and health hazards. This review offers a comprehensive overview of the historical and synthetic background of quinone electrosynthesis, highlighting its importance and relevance.</div><div>2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155801"},"PeriodicalIF":1.5,"publicationDate":"2025-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144918133","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
Synthesis of active pharmaceutical ingredient atomoxetine via desulfurative halogenation 活性药物成分托莫西汀的脱硫卤化合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-29 DOI: 10.1016/j.tetlet.2025.155800
Giovanni Roviello , Caterina Cioffi , Maria Moccia , Malachi W. Gillick-Healy , Brian G. Kelly , Mauro F.A. Adamo
{"title":"Synthesis of active pharmaceutical ingredient atomoxetine via desulfurative halogenation","authors":"Giovanni Roviello ,&nbsp;Caterina Cioffi ,&nbsp;Maria Moccia ,&nbsp;Malachi W. Gillick-Healy ,&nbsp;Brian G. Kelly ,&nbsp;Mauro F.A. Adamo","doi":"10.1016/j.tetlet.2025.155800","DOIUrl":"10.1016/j.tetlet.2025.155800","url":null,"abstract":"<div><div>An innovative preparation of the Active Pharmaceutical Ingredient (API) Atomoxetine has been developed. Key advantages of the synthetic procedure include: a one-pot preparation of a 1,3-bis-electrophilic phenyl-propionic synthon obtained <em>via</em> desulfurative chlorination of an easy to make thiophenyl sulfide; an unreported strategy for the preparation of secondary amines. The synthesis involves a total of four consecutive steps from unexpensive and readily available reagents and employes mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155800"},"PeriodicalIF":1.5,"publicationDate":"2025-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144913807","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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