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Microwave‐Assisted Multicomponent Synthesis of Spirooxindole Dihydropyridine Bisphosphonates 微波辅助多组分合成双膦酸螺菌吲哚二氢吡啶
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202400873
Bettina Rávai , Áron Soma Németh , Zsolt Kelemen , Erika Bálint
{"title":"Microwave‐Assisted Multicomponent Synthesis of Spirooxindole Dihydropyridine Bisphosphonates","authors":"Bettina Rávai ,&nbsp;Áron Soma Németh ,&nbsp;Zsolt Kelemen ,&nbsp;Erika Bálint","doi":"10.1002/ejoc.202400873","DOIUrl":"10.1002/ejoc.202400873","url":null,"abstract":"<div><div>A new, simple, catalyst‐ and solvent‐free microwave (MW)‐assisted multicomponent method was elaborated for the synthesis of spirooxindole dihydropyridine bisphosphonates as a new family of compounds by the one‐pot reaction of isatins, β‐ketophosphonates and primary amines. The synthesis was carefully optimized in respect of the molar ratio of the starting materials, the heating mode, the temperature, the reaction time and the effect of different catalysts. The substrate scope of the synthesis was also investigated, and the novel title compounds could be prepared in moderate to good yields. A proposed mechanism for the multicomponent reaction was also provided, in which the iminophosphonate compound could mean a key intermediate through the formation of the desired spiro derivatives.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202400873"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400873","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142936508","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
Synthesis and Functionalization of Aziridines: A Perspective View from Pharmaceutical Industries
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401414
Jaehee Lee, Xuan Ju, Miseon Lee, Joyce C. Leung
{"title":"Synthesis and Functionalization of Aziridines: A Perspective View from Pharmaceutical Industries","authors":"Jaehee Lee, Xuan Ju, Miseon Lee, Joyce C. Leung","doi":"10.1002/ejoc.202401414","DOIUrl":"https://doi.org/10.1002/ejoc.202401414","url":null,"abstract":"Aziridine is the smallest nitrogen-containing heterocycle. It is not only an important synthetic target but also a useful building block for constructing nitrogen-containing biologically active molecules. Due to the unique properties and reactivity of aziridine, interest in its applications in synthetic organic chemistry and pharmaceutical industry has grown rapidly in recent years. This review highlights the significance of aziridines as end products and/or precursors of medicinally relevant molecules, scope and synthetic applications of aziridines in pharmaceutical industry in recent decades.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"268 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385882","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 Allylic Fluoride Synthesis 烯丙基氟合成研究进展
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401162
Daiki Tomon , Prof. Satoru Arimitsu
{"title":"Recent Advances in Allylic Fluoride Synthesis","authors":"Daiki Tomon ,&nbsp;Prof. Satoru Arimitsu","doi":"10.1002/ejoc.202401162","DOIUrl":"10.1002/ejoc.202401162","url":null,"abstract":"<div><div>The recent decades have witnessed considerable progress in the development of fluorinated‐building‐block strategies and direct‐fluorination techniques selectively affording allylic monofluorides and <em>gem</em>‐difluorides. For allylic monofluorides, high enantioselectivities were achieved, even for fluorinated tertiary carbons, with expanded substitution patterns on vinylic moieties enabling precise structural control over di‐, tri‐, and tetrasubstituted fluorides. Advances in defluorofunctionalization and direct C−H fluorination have addressed the limitations of raw materials and made these species more accessible. Additionally, considerable progress has been achieved in the related photoredox reactions, and electrochemistry has emerged as a valuable tool for allylic fluoride synthesis. This review summarizes the recent advances in the synthesis of allylic fluorides, focusing on transition metal catalysis, organocatalysis, and noncatalytic methodologies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401162"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874625","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
Directing‐Group‐Assisted Markovnikov Hydroximation of Styrenes Enabled by Photoredox/Cobalt Dual‐Catalysis 光氧化还原/钴双催化实现苯乙烯定向基团辅助Markovnikov氢化反应
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401156
Qian Xiao , Maojian Lu , Yonghong Xiao , Jian‐Ji Zhong
{"title":"Directing‐Group‐Assisted Markovnikov Hydroximation of Styrenes Enabled by Photoredox/Cobalt Dual‐Catalysis","authors":"Qian Xiao ,&nbsp;Maojian Lu ,&nbsp;Yonghong Xiao ,&nbsp;Jian‐Ji Zhong","doi":"10.1002/ejoc.202401156","DOIUrl":"10.1002/ejoc.202401156","url":null,"abstract":"<div><div>By the combination of acridinium salt as a photocatalyst and cobaloxime complex as a co‐catalyst, a simple and mild approach has been developed for the directing‐group‐assisted Markovnikov‐selective hydroximation of styrenes under visible‐light irradiation. Herein, the directing‐group on styrenes plays an important role for this transformation. Although the substrate scope seems to be limited, such an approach features excellent regioselectivity and high atom economy. In contrast with previous methodologies, this photoredox/cobalt dual‐catalytic system is operationally simple, and avoids the use of any other sacrificial reagents.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401156"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975555","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
Photoinduced Gem‐Difluoroallylic Ketones Formation via Selective Carbonyl – C(sp3) Bond Cleavage of β‐Ketone Alcohols 通过选择性羰基- C（sp3）键裂解β-酮醇形成光诱导宝石-二氟烯丙基酮
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401149
Qianwei Zhu , Zhong Zhang , Hongquan Yu , Chenglong Yuan , Lu Wang , Zhixiang Wang , Tiantao Liu , Hongxia Xu , Youqing Yang
{"title":"Photoinduced Gem‐Difluoroallylic Ketones Formation via Selective Carbonyl – C(sp3) Bond Cleavage of β‐Ketone Alcohols","authors":"Qianwei Zhu ,&nbsp;Zhong Zhang ,&nbsp;Hongquan Yu ,&nbsp;Chenglong Yuan ,&nbsp;Lu Wang ,&nbsp;Zhixiang Wang ,&nbsp;Tiantao Liu ,&nbsp;Hongxia Xu ,&nbsp;Youqing Yang","doi":"10.1002/ejoc.202401149","DOIUrl":"10.1002/ejoc.202401149","url":null,"abstract":"<div><div>A photoinduced reaction for the formation of <em>gem</em>‐difluoroallylic ketones via selective <em>β</em>‐scission of <em>β</em>‐ketone alcohols with <em>α</em>‐trifluoromethyl alkenes is described. This process demonstrates a broad substrate scope for both <em>β</em>‐ketone alcohols and <em>α</em>‐trifluoromethyl alkenes. The reaction is proposed to proceed via an intramolecular PCET mechanism. The core of the strategy involves the oxidative cleavage of the carbonyl – C(sp<sup>3</sup>) bond in <em>β</em>‐ketone alcohols, facilitated by a base, to release acyl radicals, followed by the rapid addition of <em>α</em>‐trifluoromethyl alkenes. Additionally, various downstream transformations were carried out with these compounds in a one‐step operation. This protocol is also applicable to corresponding alkynylation and Minisci reactions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401149"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142760036","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 Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles 通过点击环加成合成4 -氨基三唑和生成碘（III）三唑
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401273
Takumi Hayashi , Elghareeb E. Elboray , Hina Sudo , Naoko Takenaga , Hiroyuki Satake , Toshifumi Dohi
{"title":"Divergent Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles","authors":"Takumi Hayashi ,&nbsp;Elghareeb E. Elboray ,&nbsp;Hina Sudo ,&nbsp;Naoko Takenaga ,&nbsp;Hiroyuki Satake ,&nbsp;Toshifumi Dohi","doi":"10.1002/ejoc.202401273","DOIUrl":"10.1002/ejoc.202401273","url":null,"abstract":"<div><div>The divergent synthesis of 4‐amino‐1,2,3‐triazoles was accomplished through the Cu‐catalyzed cycloaddition of organic azides with alkynyliodonium(III) salts, followed by Cu‐catalyzed triazole‐amine coupling involving treatment with amines and amides. The in situ formation of 1,2,3‐triazole iodonium salts is crucial to this approach, and the utilization of a Cu‐catalyst facilitates cycloaddition and C−N bond formation. The synthesis of 1,2,3‐triazolyliodonium(III) salts proposed in this study offers advantages, including mild reaction conditions, a broad substrate scope, and operational simplicity, while also providing efficient access to a complex and diverse range of 4‐amino‐1,2,3‐triazole derivatives.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401273"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832399","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
Fluorine-containing 6-Azabicyclo[3.1.1]heptanes: Bicyclic Piperidine Analogs for Drug Discovery
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-07 DOI: 10.1002/ejoc.202500022
Anton V. Chernykh, Oleksandr S. Liashuk, Anastasiia M. Hurieva, Dmytro Lesyk, Yuliia Holota, Petro Borysko, Svitlana V. Shishkina, Dmytro M. Volochnyuk, Oleksandr O Grygorenko
{"title":"Fluorine-containing 6-Azabicyclo[3.1.1]heptanes: Bicyclic Piperidine Analogs for Drug Discovery","authors":"Anton V. Chernykh, Oleksandr S. Liashuk, Anastasiia M. Hurieva, Dmytro Lesyk, Yuliia Holota, Petro Borysko, Svitlana V. Shishkina, Dmytro M. Volochnyuk, Oleksandr O Grygorenko","doi":"10.1002/ejoc.202500022","DOIUrl":"https://doi.org/10.1002/ejoc.202500022","url":null,"abstract":"Convenient synthetic approaches to a series of fluorinated bicyclic piperidine analogs (including 3-fluoro-, 3,3-difluoro-, 3-carboxy-3-fluoro-, and 3-trifluoromethyl-substituted 6-azabicyclo­[3.1.1]heptanes) were proposed. Using commercially available fluorination agents, the target building blocks were prepared in gram to decagram scale in a single run. Evaluation of pKa and LogP values revealed the importance of the fluorine-containing substituent and methylene bridge relative disposition for the compound’s physicochemical properties. Analysis of molecular structure using the exit vector plot (EVP) approach revealed negligible change in molecules conformation upon fluorination.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"85 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143371493","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
Chemoselective Synthesis of Tetrahydropyrimidines and Dihydropyrrolidones through Three-Component Reaction of Amines, 1,3,5-Triazinanes, and Alkyne Esters
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-07 DOI: 10.1002/ejoc.202401400
Wen-Kang Wang, Jian Zheng, Sheng-Yin Zhao
{"title":"Chemoselective Synthesis of Tetrahydropyrimidines and Dihydropyrrolidones through Three-Component Reaction of Amines, 1,3,5-Triazinanes, and Alkyne Esters","authors":"Wen-Kang Wang, Jian Zheng, Sheng-Yin Zhao","doi":"10.1002/ejoc.202401400","DOIUrl":"https://doi.org/10.1002/ejoc.202401400","url":null,"abstract":"A three-component reaction of amines, 1,3,5-triazinanes, and alkyne esters for the construction of tetrahydropyrimidines and dihydropyrrolidones derivatives was reported. Shifting the substituent group of 1,3,5-triazinanes led to the chemoselective synthesis. As three-atom synthons, aryl substituted 1,3,5-triazinanes were applied to the regioselective synthesis of tetrahydropyrimidines. Alkyl substituted 1,3,5-triazinanes working as two-atom synthons promoted intramolecular cyclization to generate dihydropyrrolidones analogues. The practicality of the developed methods was demonstrated by easy operation, catalyst-free conditions, and good functional groups tolerance.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258795","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
Strategies for modification of tryptophan residues: recent advances and future perspectives in photo-/ electrochemical-induction, and metal catalysis
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-07 DOI: 10.1002/ejoc.202401214
Chaochao Zhang, Jun Huang, Shun Li, Fujin Huo, Yue Weng
{"title":"Strategies for modification of tryptophan residues: recent advances and future perspectives in photo-/ electrochemical-induction, and metal catalysis","authors":"Chaochao Zhang, Jun Huang, Shun Li, Fujin Huo, Yue Weng","doi":"10.1002/ejoc.202401214","DOIUrl":"https://doi.org/10.1002/ejoc.202401214","url":null,"abstract":"Recent advancements in tryptophan (Trp) modification have greatly expanded its applications across drug discovery, materials science, and environmental monitoring. Trp, an essential amino acid with a unique indole ring, serves as an ideal target for chemical modification due to its redox-active nature. Photo- and electrochemical methods, which utilize light and electric energy, respectively, offer precise, efficient, and environmentally friendly approaches for Trp modification. Photochemical-induced transformations improve Trp's optical properties, such as fluorescence, enhancing its utility in bioimaging and sensor applications, while also introducing bioactive functional groups. Electrochemical modifications enable controlled oxidation and reduction, facilitating the selective addition of functional groups like hydroxyl or amino groups, essential for synthesizing Trp derivatives aimed at protein modulation. Additionally, metal-catalyzed reactions using transition metals such as palladium or copper enable site-selective modifications through C-H activation and cross-coupling, creating Trp derivatives with enhanced properties for optoelectronic and biomedical applications. These advancements highlight the potential of Trp-based bioconjugation strategies across diverse scientific disciplines.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258797","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 of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1002/ejoc.202500033
Julien Janssens, Guillaume Berionni, Raphael Robiette
{"title":"Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity","authors":"Julien Janssens, Guillaume Berionni, Raphael Robiette","doi":"10.1002/ejoc.202500033","DOIUrl":"https://doi.org/10.1002/ejoc.202500033","url":null,"abstract":"We report our results on the development of the Peterson olefination using gem‐borylsilylmethane derivatives to synthesize di‐ and tri‐substituted vinyl boronates. We show that the electronic properties of the carbonyl partner have no effect on the Peterson/boron‐Wittig chemoselectivity whereas the nature of the silane group plays an important role. A DFT study helps explain observed reactivity, chemoselectivity and stereoseletivity","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192193","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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