European Journal of Organic Chemistry最新文献_第6页

Synthesis of Rare‐Bacterial Sugar Analogs: Thomosamine and Fluorinated Thomosamine 稀有细菌糖类似物的合成：托莫胺和氟化托莫胺

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500523

Sam Bahadori , Mathilde Grosset‐Magagne , Denis Giguère

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Synthesis of Long‐Chain Dimethylalkyl Methyl Ethers, Important Components of the Epicuticular Wax of Spiders 蜘蛛表皮蜡重要成分长链二甲基烷基甲醚的合成

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500416

Moritz Gerbaulet , Tatsuya Kiuchi , Stefan Schulz

{"title":"Synthesis of Long‐Chain Dimethylalkyl Methyl Ethers, Important Components of the Epicuticular Wax of Spiders","authors":"Moritz Gerbaulet , Tatsuya Kiuchi , Stefan Schulz","doi":"10.1002/ejoc.202500416","DOIUrl":"10.1002/ejoc.202500416","url":null,"abstract":"<div><div>Long‐chain methyl‐branched alkyl methyl ethers are essential constituents of the cuticle of many spiders, regulating water balance and transporting chemical signals used in species recognition. The synthesis of such compounds, or related hydrocarbons found in insects, is usually time‐consuming and not very efficient, mainly due to the long alkyl chains involved. Herein, new strategies for synthesizing such compounds are evaluated. Negishi sp2–sp3 coupling reactions are first investigated and proceed with yields of 50–70%, even with very long alkyl chains. However, such approaches require the synthesis of vinyl iodides, adding additional steps. While the methyl branches are created early in these syntheses, a late introduction strategy proves more favorable. To facilitate this, chain construction is achieved through the addition of an alkynyl anion to aldehydes, resulting in internal propargyl alcohols that serve as substrates for nucleophilic methylation. Iron‐catalyzed methyl Grignard addition yields methylallyl alcohols, which are subsequently converted into the target compounds through hydrogenation and alcohol defunctionalization. Although this approach is successful for compounds with medium chain length, it fails for very long compounds. Instead, allene formation by nucleophilic addition of the methyl group to propargyl mesylates, followed by hydrogenation, gives good yields and clean target ethers.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500416"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144710697","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}

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Nickel-Catalyzed Cross Coupling of N-Alkenyl Heterocycles and Aryl Sulfonium Salts: Expedient Access to N-Benzyl Heterocycles 镍催化n -烯基杂环与芳基磺酸盐的交叉偶联：n -苄基杂环的便捷途径

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202500608

Junbiao Wu, Lun Li, Deyun Qian

{"title":"Nickel-Catalyzed Cross Coupling of N-Alkenyl Heterocycles and Aryl Sulfonium Salts: Expedient Access to N-Benzyl Heterocycles","authors":"Junbiao Wu, Lun Li, Deyun Qian","doi":"10.1002/ejoc.202500608","DOIUrl":"https://doi.org/10.1002/ejoc.202500608","url":null,"abstract":"A nickel-catalyzed system is developed that enables the coupling between aryldibenzothiophenium salts and N-alkenyl heterocycles. Traditionally, medicinally relevant N-benzylic heterocycles are constructed via harsh substitution conditions between the N-H heterocycle and a benzyl electrophile in the presence of strong bases. The CC cross coupling strategy presents attractive potential for the synthesis of these important scaffolds, e.g., carboetomidate. Herein, it is documented that the combination of a site-selective CH dibenzothiophenation with a nickel-catalyzed C(sp3)–C(sp2) cross coupling grants access to a diverse range of synthetically useful N-benzylic heterocycles, i.e., alkylated arenes. In particular, the mild conditions and good functional group compatibility permit the rapid assembly of molecular complexity and late-stage functionalization of bioactive compounds, such as clofibrate, fenofibrate, and fenbufen, thus providing an orthogonal protocol to existing SN2 and CN coupling approaches.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"99 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145141103","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}

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1,3-Diazetidin-2-Ones: Synthetic Approaches and Therapeutic Promise within the Aza-β-Lactam Family 1,3-二氮杂苷-2- one: Aza-β-内酰胺家族的合成方法和治疗前景

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202500747

Jozef Kristek, Jiří Pospíšil

{"title":"1,3-Diazetidin-2-Ones: Synthetic Approaches and Therapeutic Promise within the Aza-β-Lactam Family","authors":"Jozef Kristek, Jiří Pospíšil","doi":"10.1002/ejoc.202500747","DOIUrl":"https://doi.org/10.1002/ejoc.202500747","url":null,"abstract":"1,3-diazetidin-2-ones, overlooked members of the aza-β-lactam family, are structurally distinct four-membered nitrogen-containing heterocycles with strong potential in medicinal chemistry, particularly as β-lactamase inhibitors and antibiotic analogues. This review provides a comprehensive overview of their synthesis, structural diversity, and biological significance. The most established synthetic method is the [2 + 2] cycloaddition between CN nucleophiles and isocyanates, though this approach is highly substrate dependent and frequently leads to side products or cycloreversion. Alternative strategies—including photochemical and organometallic methodologies—have been explored but remain limited in scope. As a result, access to 1,3-diazetidin-2-ones is significantly constrained, impeding wider investigation and application. In silico studies suggest favorable stability and reactivity profiles and indicate these compounds could circumvent β-lactam resistance through hydrolysis-resistant enzyme intermediates. Several derivatives have demonstrated promising antibacterial, antifungal, antioxidant, and anticancer activities. Nevertheless, further synthetic innovation is essential to fully realize the therapeutic potential of this underexplored class of heterocycles.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145134249","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}

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Influence of Levulinoyl Protecting Groups on Glycosylation Stereoselectivity and Glycosyl Cation Structure 左旋丙烯基保护基团对糖基化立体选择性和糖基阳离子结构的影响

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202500732

Niklas Geue, Kim Greis, Sabrina Omoregbee-Leichnitz, Carla Kirschbaum, Chun-Wei Chang, Gerard Meijer, Gert von Helden, Peter H. Seeberger, Kevin Pagel

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Palladium-Catalyzed Four-Component Radical Carbonylation Reaction for the Construction of Benzofuranamide Derivativesitle 钯催化四组分自由基羰基化反应构建苯并呋喃酰胺衍生物

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202500539

Xiao-Jun Liu, Xian-Ming Gao, Dong-Yu Miao, Ming Li, Shun-Xi Li, Dong-Pin Chen, Yi-feng Qiu, Zheng-Jun Quan, Xi-Cun Wang, Yong-Min Liang

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Palladium-Catalyzed Acyl Suzuki–Miyaura Coupling from Carboxylic Acids In Situ Activated by HATU: An Efficient Way to Ketones Laid by Nitrogen Coordination HATU原位活化的钯催化羧酸酰基Suzuki-Miyaura偶联：氮配位制备酮的有效途径

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202500799

Hui You, Daming Liu, Junyu Pan, Shuo Zhang, Chaoren Shen, Mengmeng Zhao, Wanfang Li

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Fast Nucleophilic Approach to Exhaustively Substituted Porphyrin Derivatives at the “Eastern Half” “东半部”全取代卟啉衍生物的快速亲核方法

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-25 DOI: 10.1002/ejoc.202401054

Agnieszka Mikus, Sylwia Ostrysz, Stanisław Ostrowski

{"title":"Fast Nucleophilic Approach to Exhaustively Substituted Porphyrin Derivatives at the “Eastern Half”","authors":"Agnieszka Mikus, Sylwia Ostrysz, Stanisław Ostrowski","doi":"10.1002/ejoc.202401054","DOIUrl":"https://doi.org/10.1002/ejoc.202401054","url":null,"abstract":"meso-Tetraarylporphyrin chelates (of Zn2+, Ni2+, and Cu2+) are easily available from parent porphyrins. Their reactions with nitric acid (yellow fuming HNO3, d = 1.52, diluted to 25%–50%), under optimized conditions in CHCl3 at room temperature, can be carried out selectively, thus giving mainly β,β-dinitro-substituted moieties (usually two or three isomers of the above complexes). These intermediates (obtained in overall yields of up to 73%), upon the reaction with carbanions bearing a leaving group X at the reactive center, afford the target products, the ones of vicarious nucleophilic substitution (VNS) of hydrogen. This approach allows the synthesis of porphyrin derivatives exhaustively β-substituted in the so-called “Eastern half”, starting from a simple meso-tetraarylporphyrins. These types of products are sought in anticancer photodynamic therapy (PDT). Thus, the above two-step procedure including very attractive VNS reaction gives hydrophilic or amphiphilic moieties that seem to be potential PDT agents with unique structures, being practically unavailable by any other alternative methods.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145134248","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}

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Front Cover: Mild Photocatalytic Hydrodecarboxylation of Fatty Acid Derivatives using Xanthene Dyes for Biomass Valorization (Eur. J. Org. Chem. 34/2025) 前封面：使用杂蒽染料进行脂肪酸衍生物的轻度光催化加氢脱羧，用于生物质增值。j . Org。化学34/2025)

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-24 DOI: 10.1002/ejoc.70118

Jhudson G. L. de Araujo, Thays L. Lemos, Walber M. de O. Domingos, Maria do S. B. da Silva, Pedro H. do N. Silva, Aecia S. D. dos Anjos, Carlos A. Martínez-Huitle, Elisama V. dos Santos, Amanda D. Gondim, Lívia N. Cavalcanti

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Visible‐Light‐Induced α‐C(sp3)‐H Alkylation of 1,3,4‐Oxadiazoles via 1,2‐Hydrogen Atom Transfer 可见光诱导1,2 -氢原子转移1,3,4 -恶二唑的α - C(sp3) - H烷基化反应

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500605

Yafei Zhu , Dongqin He , Hui Sun , Mi Wang , Cuimei Zhang , Jian Chen , Guanghui Lv , Yong Wu

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