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Electrochemical Tandem Cyclization of N‐(But‐3‐en‐1‐yl)Anilines to Access Trifluoromethylated Tetrahydroquinoline Derivatives N - (But - 3 - en - 1 - yl)苯胺的电化学串联环化制备三氟甲基化四氢喹啉衍生物
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-09 DOI: 10.1002/ejoc.202500634
Hao Zhang, Xue Yang, YuXin Ding, Weike Su, Changjun Zhang, Yuanyuan Xie
{"title":"Electrochemical Tandem Cyclization of N‐(But‐3‐en‐1‐yl)Anilines to Access Trifluoromethylated Tetrahydroquinoline Derivatives","authors":"Hao Zhang, Xue Yang, YuXin Ding, Weike Su, Changjun Zhang, Yuanyuan Xie","doi":"10.1002/ejoc.202500634","DOIUrl":"https://doi.org/10.1002/ejoc.202500634","url":null,"abstract":"A novel electrochemical cascade strategy enables dual CC bond formation through trifluoromethylation and C(sp<jats:sup>2</jats:sup>)‐H functionalization of <jats:italic>N</jats:italic>‐(but‐3‐en‐1‐yl)anilines derivatives. This protocol efficiently constructs structurally diverse trifluoromethylated tetrahydroquinoline derivatives in moderate to good yields. It operates under mild reaction conditions, uses readily available substrates, proceeds without metal catalysts, and achieves the construction of two CC bonds in a single step. Detailed mechanistic studies demonstrate that a sequential single‐electron transfer (SET) process triggers the radical cascade reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"114 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145247034","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
XXIV Simposio Nacional de Química Orgánica (XXIV SINAQO) - Special Collection
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-09 DOI: 10.1002/ejoc.202500796
Noelia S. Medrán, Martín J. Riveira, Agustina La-Venia, Guillermo R. Labadie
{"title":"XXIV Simposio Nacional de Química Orgánica (XXIV SINAQO) - Special Collection","authors":"Noelia S. Medrán, Martín J. Riveira, Agustina La-Venia, Guillermo R. Labadie","doi":"10.1002/ejoc.202500796","DOIUrl":"https://doi.org/10.1002/ejoc.202500796","url":null,"abstract":"The XXIV Simposio Nacional de Química Orgánica (XXIV SINAQO), organised by the Sociedad Argentina de Investigación en Química Orgánica (SAIQO), was held in Rosario, Argentina, and brought together near 500 participants from across the country and abroad.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"128 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145247210","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 Cyclization of Vinyl Isocyanides with Diaryl Disulfides/1,2‐Dialkyldiselanes for the Synthesis of 1‐Substituted Isoquinolines 乙烯基异氰酸酯与二芳基二硫化物/1,2 -二烷基二烷的可见光诱导环化合成1 -取代异喹啉
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-09 DOI: 10.1002/ejoc.202500715
Yong‐Xin Liang, Qing‐Wen Ai, Xue‐Cen Xu, Yu‐Long Zhao
{"title":"Visible‐Light‐Induced Cyclization of Vinyl Isocyanides with Diaryl Disulfides/1,2‐Dialkyldiselanes for the Synthesis of 1‐Substituted Isoquinolines","authors":"Yong‐Xin Liang, Qing‐Wen Ai, Xue‐Cen Xu, Yu‐Long Zhao","doi":"10.1002/ejoc.202500715","DOIUrl":"https://doi.org/10.1002/ejoc.202500715","url":null,"abstract":"Isoquinoline compounds, especially 1‐substituted derivatives, have garnered considerable attention due to their ubiquitous presence in natural products and pharmaceuticals. Herein, a novel visible‐light‐induced tandem cyclization of vinyl isocyanides with diaryl disulfides or 1,2‐dialkyldiselanes has been developed. The reaction tolerates a wide range of substrates and provides an environmentally friendly route to the synthesis of 1‐thio/selenoisoquinolines from the easily available starting materials in a single step.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145246980","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
Amidine Syntheses from Classic to Contemporary for Medicinal Lead Compounds and Natural Products 从经典到现代的药用先导化合物和天然产物的氨基合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-09 DOI: 10.1002/ejoc.202500400
Wyatt R. Swift-Ramirez, Gregory A. Weiss
{"title":"Amidine Syntheses from Classic to Contemporary for Medicinal Lead Compounds and Natural Products","authors":"Wyatt R. Swift-Ramirez, Gregory A. Weiss","doi":"10.1002/ejoc.202500400","DOIUrl":"https://doi.org/10.1002/ejoc.202500400","url":null,"abstract":"For close to 150 years, the Pinner reaction between nitriles and amines dominated the syntheses of amidines. Today, the Pinner reaction remains highly over-represented in recent syntheses of unsubstituted or simple amidines. However, a number of greener amidine syntheses unlock access to more complex, highly substituted amidines, or closely related derivatives such as <i>N</i>-sulfonyl amidines. This review surveys recent advances in amidines and related compounds, including methods to install them and bioactive molecules prominently featuring the amidine functionality. Complex amidines are readily synthesized using both traditional and multicomponent reactions, which often involve metals. Recent trends include metal-free methodologies and expanded structural diversity of amidine products. The second half of this article reviews the utility of amidines as carbonyl bioisosteres for natural products, functional linkers, or as a bioactive functional group. The biological activities of recently reported amidine-based compounds will be surveyed with an emphasis on promising antibacterial and antiproliferative compounds.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145247211","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
Ultrasound-Assisted In-Water [3 + 2] Cycloaddition for the Synthesis of Fused Pyrrolizidine and Indolizidine Scaffolds with Anticancer Activity 超声辅助水中[3 + 2]环加成合成具有抗癌活性的吡咯利西啶和吲哚利西啶融合支架
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-09 DOI: 10.1002/ejoc.202500690
Kaushal Naithani, Arka Das, Mendragutti Shireesha, Mamta Kumari, Subhadeep Roy, Subhendu Bhowmik
{"title":"Ultrasound-Assisted In-Water [3 + 2] Cycloaddition for the Synthesis of Fused Pyrrolizidine and Indolizidine Scaffolds with Anticancer Activity","authors":"Kaushal Naithani, Arka Das, Mendragutti Shireesha, Mamta Kumari, Subhadeep Roy, Subhendu Bhowmik","doi":"10.1002/ejoc.202500690","DOIUrl":"https://doi.org/10.1002/ejoc.202500690","url":null,"abstract":"An ultrasound-assisted in-water intramolecular (3 + 2) cycloaddition reaction is reported for the synthesis of fused-pyrrolizidine and indolizidine frameworks. This approach eliminates the need for organic solvents, harsh reagents, and high temperatures. The method's practicality is demonstrated by gram-scale synthesis, and the anticancer properties of the resulting compounds against the triple-negative breast cancer cell line are demonstrated.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"122 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145255778","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
Modular Synthesis of 3,4-Disubstituted Pyrroles Through Three-Component Van Leusen Reaction of Propargylamines with Tosylmethyl Isocyanide and Water 丙胺与异氰酸甲酯及水的三组分Van Leusen反应模块化合成3,4-二取代吡咯
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-08 DOI: 10.1002/ejoc.202500855
Binbin Fei, Yangzilin Kong, Yanan Liu, Ni Gu, Qiang Tang, Yongjia Shang, Xinwei He
{"title":"Modular Synthesis of 3,4-Disubstituted Pyrroles Through Three-Component Van Leusen Reaction of Propargylamines with Tosylmethyl Isocyanide and Water","authors":"Binbin Fei, Yangzilin Kong, Yanan Liu, Ni Gu, Qiang Tang, Yongjia Shang, Xinwei He","doi":"10.1002/ejoc.202500855","DOIUrl":"https://doi.org/10.1002/ejoc.202500855","url":null,"abstract":"A novel three-component van Leusen strategy has been developed for the efficient and straightforward synthesis of valuable 3,4-disubstituted pyrroles from easily available propargylamines, tosylmethyl isocyanide, and water. This transformation advances through the formation of a pyrrole framework via [3 + 2] cycloaddition with tosylmethyl isocyanide and a sequential nucleophilic substitution, ring-opening, and deprotonation/protonation cascade process. This reaction provides a convenient modular access to pyrrole derivatives with aryl and benzoyl groups through the formation of three new bonds and one heterocycle from readily available acyclic precursors in a single step.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145247212","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
Oxidative Functionalization of Amines Using an Electrocatalytic Aminoxyl-Mediated Reaction: Preparation of N-Benzylidenebenzylamines from Benzylamines 氨基氧基介导的电催化氧化功能化反应：用苯胺制备n -苄基苯胺
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-08 DOI: 10.1002/ejoc.202500720
Chelsea M. Schroeder, Ashly Gasior, Nicholas E. Leadbeater
{"title":"Oxidative Functionalization of Amines Using an Electrocatalytic Aminoxyl-Mediated Reaction: Preparation of N-Benzylidenebenzylamines from Benzylamines","authors":"Chelsea M. Schroeder, Ashly Gasior, Nicholas E. Leadbeater","doi":"10.1002/ejoc.202500720","DOIUrl":"https://doi.org/10.1002/ejoc.202500720","url":null,"abstract":"A methodology is reported for the preparation of imines from amines by means of an electrocatalytic aminoxyl-mediated reaction. It is performed using readily available electrodes in a commercially available electrochemistry apparatus and does not require the use of a reference electrode. The methodology proceeds under mild conditions and delivers good to excellent isolated yields across a range of structurally diverse benzyl amines. Selectivity is high, with imines obtained in preference to the more commonly reported nitriles, and the process is readily scalable to the gram level. Operational simplicity and short reaction times make this method a valuable addition to the organic chemist's toolkit.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"344 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145247214","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
Palladium(II)-Catalyzed Distal C?H Functionalization of 8-Aminoquinolinamides: Facile Synthesis of Triarylmethane Derivatives 钯（II）催化远端C？8-氨基喹啉酰胺的H功能化：三芳基甲烷衍生物的简易合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-08 DOI: 10.1002/ejoc.202500493
Anushka Rastogi, Mohit Kumar, Manoj Kumar Gangwar, Dipankar Koley
{"title":"\u0000Palladium(II)-Catalyzed Distal C?H Functionalization of 8-Aminoquinolinamides: Facile Synthesis of Triarylmethane Derivatives","authors":"Anushka Rastogi, Mohit Kumar, Manoj Kumar Gangwar, Dipankar Koley","doi":"10.1002/ejoc.202500493","DOIUrl":"https://doi.org/10.1002/ejoc.202500493","url":null,"abstract":"Herein, a straightforward approach is reported for the palladium-catalyzed oxidative remote C<span></span>H alkylation of 8-aminoquinoline derivatives using <i>para-</i>quinone methides. This method enables selective C5-alkylation of quinolines and exhibits a site-selectivity distinct from that typically observed in convetional palladium-catalyzed sp<sup>2</sup> C<span></span>H activation. The reaction proceeds via chelation-induced remote C<span></span>H functionalization, and a broad range of quinolinamides are successfully coupled with <i>p</i>-quinone methides, demonstrating excellent substrate scope and functional group tolerance. Preliminary mechanistic studies suggest a reversible C<span></span>H metalation step as part of the catalytic cycle.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145247213","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
Spiro[3.3]heptane: A Versatile sp3‐Rich Scaffold and its Synthetic Routes Spiro[3.3]庚烷：一种多功能sp3‐富支架及其合成途径
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-07 DOI: 10.1002/ejoc.202500738
Myunggi Jung
{"title":"Spiro[3.3]heptane: A Versatile sp3‐Rich Scaffold and its Synthetic Routes","authors":"Myunggi Jung","doi":"10.1002/ejoc.202500738","DOIUrl":"https://doi.org/10.1002/ejoc.202500738","url":null,"abstract":"Among the growing class of sp<jats:sup>3</jats:sup>‐rich scaffolds, spiro[3.3]heptane stands out for its rigid, 3D structure and favorable physicochemical properties. Its 3D saturated scaffold enables access to unique, nonplanar chemical space and has been explored as a saturated bioisostere of benzene in drug design. In this review, an overview of synthetic strategies developed to construct spiro[3.3]heptane derivatives is provided. These approaches are grouped according to key synthetic strategies, including formal [2+2] cyclization and bond disconnections at C1C2 or C4 (spiro‐carbon) positions. Representative examples are presented to illustrate each method's key transformations and strategic bond formations. This review is intended to support synthetic chemists interested in employing spiro[3.3]heptane as a building block and to provide a foundation for further exploration of this emerging motif.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145235513","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
Asymmetric Hydrosilylation of Ketones Catalyzed by Diaminocyclohexane/Zinc Complexes: A Comparative Study and Mechanistic Insight 二氨基环己烷/锌配合物催化酮类不对称硅氢化反应的比较研究及其机理
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-10-07 DOI: 10.1002/ejoc.202500677
Caitlyn Dussart, Joseph El Khoury, Aline Maisse‐François, Christophe Gourlaouen, Stéphane Bellemin‐Laponnaz
{"title":"Asymmetric Hydrosilylation of Ketones Catalyzed by Diaminocyclohexane/Zinc Complexes: A Comparative Study and Mechanistic Insight","authors":"Caitlyn Dussart, Joseph El Khoury, Aline Maisse‐François, Christophe Gourlaouen, Stéphane Bellemin‐Laponnaz","doi":"10.1002/ejoc.202500677","DOIUrl":"https://doi.org/10.1002/ejoc.202500677","url":null,"abstract":"The catalytic enantioselective hydrosilylation activity of zinc is investigated in the presence of two ligands derived from cyclohexane‐1,2‐diamine: N,N′‐dibenzylcyclohexane‐1,2‐diamine (1) and a cage‐like structure composed of six cyclohexane‐1,2‐diamine units (2). The reaction proceeds rapidly, achieving complete conversion within minutes and affording alcohol products with enantiomeric excesses of up to 94%. Despite the favorable results with the cage‐like ligand (2), no significant advantage over ligand (1) is observed. In a second part, to gain insight into the reaction mechanism, various mechanistic experiments are conducted alongside density functional theory calculations. The findings suggest that ligand‐selective silylation leads to the formation of a zinc hydride species, which is likely the active catalytic intermediate in this system.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145235391","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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