European Journal of Organic Chemistry最新文献_第7页

Synthesis, Structure, and Physicochemical Properties of Doubly Fused Phenoxazine-Embedded Dithiasapphyrins 双熔接苯恶嗪包埋二硫磷的合成、结构及理化性质

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70805

Neha Tripathi, Mangalampalli Ravikanth

{"title":"Synthesis, Structure, and Physicochemical Properties of Doubly Fused Phenoxazine-Embedded Dithiasapphyrins","authors":"Neha Tripathi, Mangalampalli Ravikanth","doi":"10.1002/ejoc.70805","DOIUrl":"https://doi.org/10.1002/ejoc.70805","url":null,"abstract":"Herein, we report the synthesis of a new class of doubly fused phenoxazine-embedded dithiasapphyrins via (3 + 2) condensation of an appropriate phenoxazine-based tripyrrane with bithiophene diol in CH2Cl2 under BF3·OEt2-catalyzed conditions. Single-crystal X-ray diffraction analysis of one representative macrocycle revealed an unusual structural rearrangement involving inversion of the two thiophene rings of the bithiophene unit, followed by fusion of the inner thiophene carbon atoms with adjacent pyrrolic nitrogen atoms to generate two tripentacyclic fused rings within the dithiasapphyrin framework. The resulting macrocycle adopts a highly distorted conformation, with the phenoxazine unit deviating by 66.97° from the mean plane defined by the four meso-carbon atoms. These doubly fused phenoxazine-embedded dithiasapphyrins exhibit intense panchromatic absorption across the UV–visible region with pronounced bathochromic shifts relative to their previously reported phenothiazine-fused analogues. Protonation with TFA further extends the absorption profile into the UV–visible-near-infrared region, affording strongly red-shifted diprotonated species. Electrochemical studies revealed that the phenoxazine-fused macrocycles are more electron-rich than the corresponding phenothiazine derivatives. Density functional theory and time-dependent density functional theory studies support the experimental observations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100399","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 CH Bond Functionalization Using Traceless N-Functionalized Directing Groups 利用无迹n功能化定向组实现C - H键功能化的最新进展

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70800

Kai Liu, Suosuo Qi, Dong-Liang Pan, Kun Zhou, Dan-Qian Xu, Shao-Jie Lou

{"title":"Recent Advances in CH Bond Functionalization Using Traceless N-Functionalized Directing Groups","authors":"Kai Liu, Suosuo Qi, Dong-Liang Pan, Kun Zhou, Dan-Qian Xu, Shao-Jie Lou","doi":"10.1002/ejoc.70800","DOIUrl":"https://doi.org/10.1002/ejoc.70800","url":null,"abstract":"The chelation-assisted CH bond activation with proper directing groups not only promotes the reaction efficiency but also enables selective CC or CX bond formation at the specific positions. Among them, the traceless directing groups (TDGs) strategy is highly attractive since it allows the in situ removal of directing groups after the directed CH bond functionalization. On the other hand, N-containing substrates, e.g., N-heterocycles, amines, and oximes, are of great importance in both organic synthesis and drug discovery. The directed site-selective CH bond functionalization of nitrogen-based substrates using TDG strategy constitutes an ideal solution to access more elaborate molecules. In this context, this review focus on the development of diverse traceless N-functionalized directing groups and their application in the CH bond functionalization, along with mechanistic insights into the directing group removal steps. Typical examples that use N-functionalized TDGs, such as N-oxides, nitrones, N-nitroso groups, hydrazyl groups, N-acyl groups, and other nitrogen-functionalized groups, have been documented in this review, aiming to give a timely comprehensive overview and stimulate the development of more efficient methodologies.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100419","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

Microwave-Assisted Copper-Mediated One-Pot Sequential Synthesis of Quinolino[3,4-b]quinoxalines 微波辅助铜介导的一锅序贯合成喹啉[3,4-b]喹诺啉类化合物

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70802

Swanand Vinayak Joshi, Danaboina Srikanth, Abdul Kalam, Gaurav Pawar, Nagesh A. Bhale, Amol G. Dikundwar, Venkata Madhavi Yaddanapudi, Srinivas Nanduri

{"title":"Microwave-Assisted Copper-Mediated One-Pot Sequential Synthesis of Quinolino[3,4-b]quinoxalines","authors":"Swanand Vinayak Joshi, Danaboina Srikanth, Abdul Kalam, Gaurav Pawar, Nagesh A. Bhale, Amol G. Dikundwar, Venkata Madhavi Yaddanapudi, Srinivas Nanduri","doi":"10.1002/ejoc.70802","DOIUrl":"https://doi.org/10.1002/ejoc.70802","url":null,"abstract":"An efficient microwave-assisted one-pot protocol has been developed for the synthesis of 6-aryl/heteroarylquinolino[3,4-‍b]quinoxaline derivatives. The method involves a CuI-mediated tandem annulation of 2-(2-bromophenyl)quinoxalines with aryl and heteroaryl aldehydes, using TMSN3 as the nitrogen source. The transformation proceeds rapidly under microwave irradiation, delivering the desired products in moderate-to-excellent yields (up to 91%) with broad substrate scope. Further, benzyl alcohols (with TBHP) also serve as viable precursors under identical conditions to afford 6-aryl/heteroaryl-quinolino[3,4-b]quinoxaline derivatives. Notably, the protocol eliminates the requirement for a stoichiometric amount of reducing agent used in the earlier protocol. It can be extended to gram-scale synthesis with a remarkably reduced reaction time. Mechanistic investigations, supported by control experiments, ESI-HRMS analysis, and DFT calculations, provide insight into the reaction pathway. This approach offers a rapid, practical, and scalable route to quinolino[3,4-b]quinoxaline frameworks of potential medicinal relevance.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100400","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

Synthesis and Antiviral Evaluation of Sugar-Modified Pseudouridine Analogs 糖修饰假尿嘧啶类似物的合成及抗病毒评价

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70799

Zhiyuan Chen, Elisabetta Groaz, Jef Rozenski, Steven De Jonghe, Eveline Lescrinier

引用次数: 0

Competing Charge Transport Pathways: A Spirobifluorene-Based Molecular Loop 竞争性电荷传输途径：一个基于螺比芴的分子环

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/ejoc.70784

Brian Ogi, Riccardo Conte, Salome L. Heim, Herre S. J. van der Zant, Marcel Mayor

{"title":"Competing Charge Transport Pathways: A Spirobifluorene-Based Molecular Loop","authors":"Brian Ogi, Riccardo Conte, Salome L. Heim, Herre S. J. van der Zant, Marcel Mayor","doi":"10.1002/ejoc.70784","DOIUrl":"10.1002/ejoc.70784","url":null,"abstract":"Understanding the relationship between molecular structure and charge transport remains a crucial aspect towards integrating single molecules into electronic devices, especially in systems which feature multiple conducting pathways. Here we report the synthesis of a molecular loop that incorporates a rigid 9,9′-spirobifluorene (SBF) core as a central mounting point for thiol anchoring groups and a cycloparaphenylene (CPP) backbone. The model compound is synthesized by a Suzuki–Miyaura coupling between a CPP precursor and a functionalized SBF derivative, followed by reductive aromatization of the macrocycle. The resulting macrocycles are fully characterized and enantiomerically resolved by chiral high-performance liquid chromatography (HPLC), and their chiroptical properties are investigated. Conductance measurements in a mechanically controlled break-junction (MCBJ) setup demonstrate reproducible single-molecule junction formation with two dominant conductance plateaus near 2 × 10−4 G0 and 4 × 10−5 G0, observed across different samples and applied voltages. The observed conductance features are consistent with multiple reproducible junction configurations, highlighting the molecular loop as a promising platform for studying charge transport through multiple intramolecular pathways.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.70784","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148768594","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Solid-State Melt Rearrangement/Acetylation Reaction of Primary Amides and PhI(OAc)2 in Reactive Eutectic Medium 反应共晶介质中伯胺与PhI(OAc) 2的固态熔融重排/乙酰化反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-23 DOI: 10.1002/ejoc.70789

Haoran Lv, Yang Hang, Zhongkai Wang, Taoshan Jiang

引用次数: 0

Direct Conversion of Aryl Iodides Into Benzylamines by Aminomethylation: Reaction Scope, Mechanistic Studies, and Applications 芳基碘化物经氨基甲基化直接转化为苄胺：反应范围、机理研究及应用

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/ejoc.70787

Abhijit Sen, Atsuya Muranaka, Yu Hatakenaka, Aya Ohno, Yoichi M. A. Yamada

{"title":"Direct Conversion of Aryl Iodides Into Benzylamines by Aminomethylation: Reaction Scope, Mechanistic Studies, and Applications","authors":"Abhijit Sen, Atsuya Muranaka, Yu Hatakenaka, Aya Ohno, Yoichi M. A. Yamada","doi":"10.1002/ejoc.70787","DOIUrl":"10.1002/ejoc.70787","url":null,"abstract":"Despite the high utility and value of benzylamines and their derivatives, their synthesis is hindered by a limited substrate availability and nonreusable transition-metal catalysts. To that end, this study develops an aminomethylation strategy using aryl iodides and formamides while examining the substrate scope and underlying mechanism for synthesizing benzylamines under parts-per-million-level (65 ppm) reusable palladium catalysis. This method can accommodate a wide range of substrates, including electron-rich and electron-deficient aryl, polyaryl, and heteroaryl iodides. Similarly, various formamide derivatives yield aminomethylated products. This aminomethylation strategy is used to directly synthesize biologically active molecules, such as a rivastigmine analog, and natural products, e.g., gramine. In addition, tryptamine, a serotonin receptor, and diindolylmethane, a metabolite, are successfully produced by derivatizing the aminomethylated products. Isotope-labeling experiments indicate that formamide derivatives were precursors for the reducing agent, in addition to providing both amines and carbon. A plausible catalytic pathway is proposed based on isotope-labeling experiments and density functional theory calculations, providing insights for future research and new applications in organic synthesis and medicinal chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.70787","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148768591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Exploiting Biocatalysis for the Scalable Synthesis of Enantiopure γ-Hydroxynitrile Building Blocks 利用生物催化可扩展合成对映纯γ -羟基腈构建块

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70782

Benjamin Baumert, Kathryn Yeow, Roi Boris Tchuemmogne Tchuente, Adam Cruise, Christopher Thomas, Thomas Bayer, Uwe T. Bornscheuer, Marcus Baumann

引用次数: 0

Ring‐Opening Cyclization (ROC) of Aziridines With 2‐(2‐Bromophenyl)‐1 H ‐Benzimidazoles: Rotamer Analysis and Synthesis of Benzimidazole‐Fused 1,4‐Benzodiazepine 叠氮嘧啶与2‐（2‐溴苯基）‐1 H‐苯并咪唑的开环环化（ROC）：苯并咪唑-融合1,4‐苯并二氮卓的旋转体分析和合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 DOI: 10.1002/ejoc.70879

Suraj Kashyap, Bharat Singh, Prabodh Ranjan, Shishir Singh, Ajit K. Gupta, Manas K. Ghorai

引用次数: 0

Hydrosilylation of Nitrones With Trichlorosilane: Preparation of Hydroxylamines 硝基酮与三氯硅烷的硅氢化反应：羟胺的制备

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70812

Yifan Li, Kexin Su, Yuxi Guo, Xiaohua Lei, Zixiang Wang, Qiang Wang, Ju Guo, Yongsheng Zheng

引用次数: 0