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Front Cover: Synthetic Strategies to Prepare Bioactive Lysine and Peptide Conjugates With Triazolium Derivatives (Eur. J. Org. Chem. 38/2024) 封面：用三唑鎓衍生物制备具有生物活性的赖氨酸和多肽共轭物的合成策略（欧洲有机化学杂志 38/2024）
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-11 DOI: 10.1002/ejoc.202483801
Patrycja Ledwoń, Michał Jewginski, Claudia Bello, Francesca Nuti, Paolo Rovero, Rafal Latajka, Anna Maria Papini
{"title":"Front Cover: Synthetic Strategies to Prepare Bioactive Lysine and Peptide Conjugates With Triazolium Derivatives (Eur. J. Org. Chem. 38/2024)","authors":"Patrycja Ledwoń,&nbsp;Michał Jewginski,&nbsp;Claudia Bello,&nbsp;Francesca Nuti,&nbsp;Paolo Rovero,&nbsp;Rafal Latajka,&nbsp;Anna Maria Papini","doi":"10.1002/ejoc.202483801","DOIUrl":"10.1002/ejoc.202483801","url":null,"abstract":"<p><b>The Front Cover</b> shows a set of <i>Safirinium</i>-dye derivatives used for the facile preparation of peptide conjugates as potential elastase inhibitors, by exploiting a lysine side chain as an effective linker between the dye and the peptide. With an optimized peptide sequence forming the core and triazolium derivatives acting as particular caps, we can create molecular tools capable of tuning the activity of a selected enzyme. Details of this approach are reported in the Research Article by R. Latajka, A. M. Papini and co-workers (DOI: 10.1002/ejoc.202400399). Structure taken from PDB ID: 1QR3.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 38","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202483801","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142415612","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
Hypervalent Iodine Catalyzed Cascade C–H Functionalization: An Atom-Economical Strategy to Access Diverse 2-Substituted Benzothiazoles 高价碘催化级联 C-H 功能化：获得多种 2-取代苯并噻唑的原子经济学策略
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-10 DOI: 10.1002/ejoc.202401043
Santhosh Kumar Alla, Kotari Shakeena, Bokka Srinivas, Thammana Subha Sai Sriram, Leela Prasad Chamanthula, Kiran Indukuri, Muthyala Murali Krishna Kumar
{"title":"Hypervalent Iodine Catalyzed Cascade C–H Functionalization: An Atom-Economical Strategy to Access Diverse 2-Substituted Benzothiazoles","authors":"Santhosh Kumar Alla, Kotari Shakeena, Bokka Srinivas, Thammana Subha Sai Sriram, Leela Prasad Chamanthula, Kiran Indukuri, Muthyala Murali Krishna Kumar","doi":"10.1002/ejoc.202401043","DOIUrl":"https://doi.org/10.1002/ejoc.202401043","url":null,"abstract":"A metal-free, 4,5-difluoro-2-iodobenzoic acid-catalyzed C–H functionalization strategy is developed for the synthesis of 2-(hetero)aryl benzothiazoles from aryl isothiocyanates and unfunctionalized arenes/thiophenes/furans at room temperature. The procedure entails a one-pot, cascade carbon–carbon and carbon–sulfur bond formation facilitated by triflic acid, which serves as both a Bronsted acid and a ligand source at the in situ generated I(III) centre. This process is atom-economical and offers benefits over existing protocols for synthesizing benzothiazoles in terms of ease of use, eco-friendliness, and not requiring the typical use of aryl aldehyde/carboxylic acid precursors. Mechanistic studies were carried out, and the synthetic utility of the protocol was demonstrated for the synthesis of the benzothiazole-based antitumor drug GW-610.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398556","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
Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions 在温和条件下使用卤化脒盐作为卤素源快速、普遍地获取 α-卤代羰基化合物
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-09 DOI: 10.1002/ejoc.202401111
Lewan Li, Mengxiang Luo, Shuntian Liu, Jian Lv, Jie Zeng, Qiongjiao Yan, Jie Liao, Haifeng Wang, Shuangxi Gu
{"title":"Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions","authors":"Lewan Li, Mengxiang Luo, Shuntian Liu, Jian Lv, Jie Zeng, Qiongjiao Yan, Jie Liao, Haifeng Wang, Shuangxi Gu","doi":"10.1002/ejoc.202401111","DOIUrl":"https://doi.org/10.1002/ejoc.202401111","url":null,"abstract":"Rapid and efficient construction of α‐haloketones with diazo compounds and amidine·HX (X = Cl, Br, I) salts as halogen sources has been recognized as a simple and practical strategy. The reaction exhibits a broad scope and scalability, thereby enabling synthesis of a broad spectrum of functionally orchestrated α‐haloketones under mild and metal‐free conditions in a short time. Control experiments established the involvement of triffate 11 in the mechanism","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"83 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142397774","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
One-Pot Synthesis of Semisaturated Fused Polycyclic Iminosugars by a Diels-Alder Reaction 通过 Diels-Alder 反应一锅合成半饱和融合多环氨基糖
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-09 DOI: 10.1002/ejoc.202401005
Song Xie, jilai Wu, Likai Zhou, Chao Wei, Xiaoliu Li, Hua Chen
{"title":"One-Pot Synthesis of Semisaturated Fused Polycyclic Iminosugars by a Diels-Alder Reaction","authors":"Song Xie, jilai Wu, Likai Zhou, Chao Wei, Xiaoliu Li, Hua Chen","doi":"10.1002/ejoc.202401005","DOIUrl":"https://doi.org/10.1002/ejoc.202401005","url":null,"abstract":"Abstract: A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 °C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"79 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398341","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
Strategy for C–H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology Cubanes 的 C-H 功能化策略：从化学反应到催化方法
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-09 DOI: 10.1002/ejoc.202401055
Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi
{"title":"Strategy for C–H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology","authors":"Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi","doi":"10.1002/ejoc.202401055","DOIUrl":"https://doi.org/10.1002/ejoc.202401055","url":null,"abstract":"We summarized a strategy for C–H functionalization of cubanes, highlighting recent progress in the field. Cubane, known as a bioisostere of benzene ring, and its functionalization hold significant potential for future drug development. However, owing to its highly strained and thermodynamically unstable nature, the methodologies are limited and their precise and diverse functionalization is challenging in current organic chemistry. In this Concept, we categorized and explained these methodologies, which represents a majority of current cubane C–H functionalization. In addition, we discussed recent advancements in catalytic C–H functionalization methods, demonstrating their potential to address these challenges effectively.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"108 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142397853","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
Divergent Annulations of 5,6-Dihydro-4H-1,2-Oxazine N-Oxides and Enol Diazoacetates for the Switchable Chemoselective Synthesis of Fused 1,2-Oxazine Derivatives 5,6-二氢-4H-1,2-恶嗪 N-氧化物与烯醇重氮乙酸酯的不同环化反应，用于可切换的化学选择性合成融合的 1,2-恶嗪衍生物
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-09 DOI: 10.1002/ejoc.202400768
Stepan N. Ostarkov, Yana I. Lichtenstein, Yulia A. Antonova, Yulia V. Nelyubina, Vladislav K. Lesnikov, Andrey Tabolin
{"title":"Divergent Annulations of 5,6-Dihydro-4H-1,2-Oxazine N-Oxides and Enol Diazoacetates for the Switchable Chemoselective Synthesis of Fused 1,2-Oxazine Derivatives","authors":"Stepan N. Ostarkov, Yana I. Lichtenstein, Yulia A. Antonova, Yulia V. Nelyubina, Vladislav K. Lesnikov, Andrey Tabolin","doi":"10.1002/ejoc.202400768","DOIUrl":"https://doi.org/10.1002/ejoc.202400768","url":null,"abstract":"Reactions of 5,6-dihydro-4H-1,2-oxazine N-oxides with enol diazoacetates were studied. A particular reaction path depends on the amount of catalyst and the order of the addition of the substrates. Use of Rh2(Oct)4 (2 mol.%) leads to chemoselective [3+3]-annulation producing 1,2-oxazine-fused 1,2-oxazine derivatives. With lower catalyst loadings (0.03 mol.%) enol diazoacetates are converted to cyclopropene derivatives, which in situ react with 1,2-oxazine N-oxides via tandem [3+2]-cycloaddition-rearrangement producing oxazine-fused aziridines. Both transformations showed a wide substrate scope and produced target products with good yields and diastereoselectivity, thus allowing selective preparation of these rare heterocyclic systems. A mechanistic rationale for observed chemo- and stereo- selectivities was proposed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385453","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
A new CuI/oxalamide catalytic system for the large-scale aerobic oxidation of alcohols 用于大规模醇类有氧氧化的新型 CuI/oxalamide 催化系统
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/ejoc.202400804
Kexue Xing, Jicong Xiang, Zijin Luo, Guiyuan Liu, Xianghao Zhang, Guofu Zhang, Chengrong Ding
{"title":"A new CuI/oxalamide catalytic system for the large-scale aerobic oxidation of alcohols","authors":"Kexue Xing, Jicong Xiang, Zijin Luo, Guiyuan Liu, Xianghao Zhang, Guofu Zhang, Chengrong Ding","doi":"10.1002/ejoc.202400804","DOIUrl":"https://doi.org/10.1002/ejoc.202400804","url":null,"abstract":"Since the report of oxamide ligands, they have been widely used for the efficient construction of various types of C-X (such as C, N, O and S) bonds. To evaluate whether the easily tunable electronic properties and unique coordination modes of oxamide ligands can also shine in the field of oxidation, we initiated a study on oxamide ligand/copper/air oxidation and applied it to the oxidation of alcohols to assess its practicality and potential applications. The practicality of this strategy was further verified through scale-up reactions on a 100 mmol scale and gram-scale derivatization of pharmaceutical molecules.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385454","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
Oligonucleotides Containing 8,1′‐Ethano‐2′‐deoxyadenosine: Synthesis and Properties 含 8,1′-乙氰基-2′-脱氧腺苷的寡核苷酸：合成与性质
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/ejoc.202400849
Honoka Hanashiro, Yuta Ito, Yasufumi Fuchi, Yoshiyuki Hari
{"title":"Oligonucleotides Containing 8,1′‐Ethano‐2′‐deoxyadenosine: Synthesis and Properties","authors":"Honoka Hanashiro, Yuta Ito, Yasufumi Fuchi, Yoshiyuki Hari","doi":"10.1002/ejoc.202400849","DOIUrl":"https://doi.org/10.1002/ejoc.202400849","url":null,"abstract":"This article presents the synthesis and properties of oligonucleotides containing 8,1′‐ethano‐2′‐deoxyadenosine (ethano‐dA) in which the adenine base (ethA) is fixed to the syn conformation. Ethano‐dA phosphoramidite was synthesized by using a 1,5‐hydrogen‐atom transfer/radical cyclization process and introduced into oligonucleotides, which were successfully obtained by employing the 4,4′‐dimethoxytrityl‐off synthesis mode. The duplex‐forming ability of the oligonucleotides containing ethano‐dA was evaluated. In the antiparallel Watson–Crick duplex, the ethA formed stable base pairs with thymine and guanine, in which two Hoogsteen‐type hydrogen bonds could be formed. By contrast, the parallel Hoogsteen duplex containing the ethA:thymine base pair showed thermal stability comparable to that containing a natural adenine:thymine base pair because ethA and thymine can form two Watson–Crick‐type hydrogen bonds. These results indicated that ethano‐dA may be helpful for elucidating the function of adenine bases via the syn conformation in DNA.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142384383","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
A Supramolecular Gel that Exhibits Multi-stimuli Responsiveness and High Conductivity Through Host-Guest Interactions 通过主客体相互作用实现多刺激响应和高传导性的超分子凝胶
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-07 DOI: 10.1002/ejoc.202400726
Bo Qin, Jie Wang, Xiaojing Wu, Hongyan Cai, Hang Li, Pizheng Zhang
{"title":"A Supramolecular Gel that Exhibits Multi-stimuli Responsiveness and High Conductivity Through Host-Guest Interactions","authors":"Bo Qin, Jie Wang, Xiaojing Wu, Hongyan Cai, Hang Li, Pizheng Zhang","doi":"10.1002/ejoc.202400726","DOIUrl":"https://doi.org/10.1002/ejoc.202400726","url":null,"abstract":"A network-structured supramolecular gel is constructed through host-guest interactions between conjugated ligands and metal ions, leading to enhanced mechanical properties and excellent electrical conductivity. This overcomes the problem of insufficient conductance due to the presence of solvent in the interstitial region of the supramolecular gel. Supramolecular gels can undergo reversible sol-gel transitions by controlling the pH or temperature of the system. In addition, a method has been developed to determine the specific binding ratio of host-guest molecules by conductivity tests, and has been used to verify the specific binding ratio of crown ether to potassium ions. To explain the high conductivity of supramolecular metallic gels, DFT and SEM have been employed to elucidate their conductivity mechanism.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142384660","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
Front Cover: Trends in the Reactivity of Pentacyclic Ether Derivatives on Silicon and Germanium Surfaces Revealed by Energy Decomposition Analysis for Extended Systems (Eur. J. Org. Chem. 37/2024) 封面：通过扩展体系的能量分解分析揭示五环醚衍生物在硅和锗表面的反应趋势（欧洲有机化学杂志 37/2024）
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-04 DOI: 10.1002/ejoc.202483701
Franz Thiemann, Hendrik Weiske, Ralf Tonner-Zech
{"title":"Front Cover: Trends in the Reactivity of Pentacyclic Ether Derivatives on Silicon and Germanium Surfaces Revealed by Energy Decomposition Analysis for Extended Systems (Eur. J. Org. Chem. 37/2024)","authors":"Franz Thiemann,&nbsp;Hendrik Weiske,&nbsp;Ralf Tonner-Zech","doi":"10.1002/ejoc.202483701","DOIUrl":"10.1002/ejoc.202483701","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the S<sub>N</sub>2-like ring-opening reactions of THF derivatives with the chalcogen elements O, S, Se and Te on both Si(001) and Ge(001) surfaces. The periodic table at the back embodies the trends presented in the work. On the left, the deformation density of the first NOCV in the THF precursor structure showcases the charge transfer towards the surface. The across-trench product of the tellurium derivative is shown on the right. The center features the across-trench transition state geometry of THSe with a deformation density indicating an S<sub>N</sub>2-like reaction. More information can be found in the Research Article by R. Tonner-Zech and co-workers (DOI: 10.1002/ejoc.202400560).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 37","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202483701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374408","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
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