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Synthesis and reactivity of 1,4-ethano-1,5-naphthyridine derivatives using microwave activation or flow chemistry
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202401443
Mazarine Laurent, Rodolphe Vatinel, Stéphane Bostyn, Sylvain Routier, Frederic Buron
{"title":"Synthesis and reactivity of 1,4-ethano-1,5-naphthyridine derivatives using microwave activation or flow chemistry","authors":"Mazarine Laurent, Rodolphe Vatinel, Stéphane Bostyn, Sylvain Routier, Frederic Buron","doi":"10.1002/ejoc.202401443","DOIUrl":"https://doi.org/10.1002/ejoc.202401443","url":null,"abstract":"The design of some novel disubstituted 3,4-dihydro-2H-1,4-ethano-1,5-naphthyridine derivatives is reported under classical and flow methodologies. The series were developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position C-2 that was then used to create C–N bond using the Chan-Lam coupling reaction or in situ C–O bond activation via palladium-catalyzed cross-coupling reactions. The conditions were optimized, and a wide range of boronic acids were used to determine the scope and limitations of each method. To complete this study, a flow Suzuki-Miyaura process was established to afford polyfunctionalized 1,4-ethano-1,5-naphthyridine derivatives in high yields with a very efficient process (10 min.).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695852","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
Harnessing Electricity in Dehydrogenative Coupling: Transition Metal-Free Synthesis of Quinoline Derivatives
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500316
Raju Dey, Vageesh M, Abhijeet Anand, Subir Panja
{"title":"Harnessing Electricity in Dehydrogenative Coupling: Transition Metal-Free Synthesis of Quinoline Derivatives","authors":"Raju Dey, Vageesh M, Abhijeet Anand, Subir Panja","doi":"10.1002/ejoc.202500316","DOIUrl":"https://doi.org/10.1002/ejoc.202500316","url":null,"abstract":"An efficient strategy is demonstrated for the electrocatalyitc synthesis of 2-aryl quinoline derivatives via an anodic dehydrogenation of 2-aminobenzyl alcohol molecules followed by condensation with carbonyl compounds at room temperature. The current protocol requires only electricity as the green oxidant, provides the desired products in good to excellent yield and is compatible with a wide range of functional groups.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695853","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
Halogen‐Mediated Electrochemical C−N Bond Construction of Amine
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401352
Yu‐Yang Xie , Zhang Zhang , Ying‐Chun Wang
{"title":"Halogen‐Mediated Electrochemical C−N Bond Construction of Amine","authors":"Yu‐Yang Xie ,&nbsp;Zhang Zhang ,&nbsp;Ying‐Chun Wang","doi":"10.1002/ejoc.202401352","DOIUrl":"10.1002/ejoc.202401352","url":null,"abstract":"<div><div>Organic electrochemical synthesis stands out for its environmentally friendly and efficient characteristics. Among these approaches, halogen‐mediated indirect electrosynthesis has gained significant attention as an efficient strategy for C−N bond formation, widely applied in the synthesis of nitrogen‐containing compounds. This review highlights recent advances in direct C−N bond formation processes for various amines under halogen‐mediated electrosynthetic conditions. The features, scope, limitations, and proposed mechanisms of these transformations are discussed in detail. We aim to provide insights into expanding the applicability of halogen‐mediated electrosynthesis, contributing to the development of sustainable synthetic methodologies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401352"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143055274","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 the Photochemical Synthesis of Esters
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401398
Jie Li , Dr. Da‐Liang Zhu , David James Young , Prof. Dr. Yanqing Wang , Prof. Dr. Hong‐Xi Li
{"title":"Recent Advances in the Photochemical Synthesis of Esters","authors":"Jie Li ,&nbsp;Dr. Da‐Liang Zhu ,&nbsp;David James Young ,&nbsp;Prof. Dr. Yanqing Wang ,&nbsp;Prof. Dr. Hong‐Xi Li","doi":"10.1002/ejoc.202401398","DOIUrl":"10.1002/ejoc.202401398","url":null,"abstract":"<div><div>Photocatalysis has recently emerged as a powerful synthetic tool for making a variety of carbon‐carbon and carbon‐heteroatom bonds. The development of esterification reactions induced by light is an atom economical and energy efficient alternative to traditional methods for the synthesis of esters, with benefits including mild reaction conditions, high chemical yields, and wide functional group tolerance. This review summarizes recent progress made in this green methodology, including mechanisms of action, substrate scope, limitations and future prospects.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401398"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192371","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: Cardo Bisphenol Fluorene Fused with Dibenzo[g,p]chrysene for a High Refractive Index Monomer (Eur. J. Org. Chem. 11/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202581101
Toko Yura, Rion Noda, Ikuma Okada, Zhenfeng Guo, Prof. Dr. Takashi Nakanishi, Prof. Dr. Yousuke Yamaoka, Prof. Dr. Tetsuo Iwasawa
{"title":"Front Cover: Cardo Bisphenol Fluorene Fused with Dibenzo[g,p]chrysene for a High Refractive Index Monomer (Eur. J. Org. Chem. 11/2025)","authors":"Toko Yura,&nbsp;Rion Noda,&nbsp;Ikuma Okada,&nbsp;Zhenfeng Guo,&nbsp;Prof. Dr. Takashi Nakanishi,&nbsp;Prof. Dr. Yousuke Yamaoka,&nbsp;Prof. Dr. Tetsuo Iwasawa","doi":"10.1002/ejoc.202581101","DOIUrl":"10.1002/ejoc.202581101","url":null,"abstract":"<p><b>The Front Cover</b> shows a cardo-typed optical material with a high refractive index (1.83) that bends and focuses light. A heptacycle precursor from fused dibenzo[<i>g</i>,<i>p</i>]chrysene (DBC) and cyclopentanone underwent double arylation to yield a cardo scaffold comparable to bis-phenol fluorene. A DBC core with a bay-ester underwent intramolecular acylation and twofold arylation to afford a DBC-linked bisphenol. Achieving a high refractive index with purely hydrocarbons supports future cardo material chemistry. More information can be found in the Research Article by T. Iwasawa and co-workers (DOI: 10.1002/ejoc.202401409).\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":"28 11","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581101","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678353","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
Photoinduced, Decarboxylative Coupling of α‐Keto Acids with Diselenides to Form Selenoesters α-酮酸与二硒酸酯光诱导脱羧偶联生成硒酸酯
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401399
Pei Qu , Haifan Wang , Ying Chen , Kanta Pajujantaro , Dr. Gong‐Qing Liu
{"title":"Photoinduced, Decarboxylative Coupling of α‐Keto Acids with Diselenides to Form Selenoesters","authors":"Pei Qu ,&nbsp;Haifan Wang ,&nbsp;Ying Chen ,&nbsp;Kanta Pajujantaro ,&nbsp;Dr. Gong‐Qing Liu","doi":"10.1002/ejoc.202401399","DOIUrl":"10.1002/ejoc.202401399","url":null,"abstract":"<div><div>A mild and green strategy for the synthesis of selenoester derivatives has been developed through photoinduced decarboxylative coupling of α‐keto acids with diselenides. This transformation proceeds smoothly without requiring any external photocatalyst, additive, or oxidant. Both diaryl and dialkyl diselenides react efficiently with α‐keto acids to produce selenoesters in good yields. Mechanistic studies suggest that the generated acyl radical is responsible for this transformation.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401399"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142929702","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
An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones 一种制备糖基β-二酮的高效合成方法
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401366
Ivan A. Barri , Macarena S. Le Pors , Prof. Dr. Pedro A. Colinas
{"title":"An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones","authors":"Ivan A. Barri ,&nbsp;Macarena S. Le Pors ,&nbsp;Prof. Dr. Pedro A. Colinas","doi":"10.1002/ejoc.202401366","DOIUrl":"10.1002/ejoc.202401366","url":null,"abstract":"<div><div>In this study, we present a synthetic methodology for preparing glycosyl β‐diketones from the corresponding allyl ethers. The process involves three steps: nitrile oxide cycloadditions, reduction of the glycosyl isoxazolines, and oxidation of β‐hydroxyketones. This route is suitable for acid‐ and base‐sensitive protecting groups, and the reactions were conducted with retention of the anomeric configuration. The resulting glycosyl β‐diketones were then utilized in the synthesis of the corresponding pyrazoles.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401366"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874612","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‐Catalyzed Heck‐Matsuda Reaction of Morita‐Baylis‐Hillman Alcohols with Aryl Triazenes: Unexpected Role of Nitric Acid as the Promoter 钯催化Morita-Baylis-Hillman醇与芳基三氮烯的Heck-Matsuda反应：硝酸作为启动子的意外作用
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401386
Yue Shen , Mengni Pan , Daming Liu , Hui You , Xinying He , Yang Li , Prof. Dr. Chaoren Shen , Dr. Mengmeng Zhao , Dr. Wanfang Li
{"title":"Palladium‐Catalyzed Heck‐Matsuda Reaction of Morita‐Baylis‐Hillman Alcohols with Aryl Triazenes: Unexpected Role of Nitric Acid as the Promoter","authors":"Yue Shen ,&nbsp;Mengni Pan ,&nbsp;Daming Liu ,&nbsp;Hui You ,&nbsp;Xinying He ,&nbsp;Yang Li ,&nbsp;Prof. Dr. Chaoren Shen ,&nbsp;Dr. Mengmeng Zhao ,&nbsp;Dr. Wanfang Li","doi":"10.1002/ejoc.202401386","DOIUrl":"10.1002/ejoc.202401386","url":null,"abstract":"<div><div>We herein developed a mild and ligand‐free palladium‐catalyzed Heck‐Matsuda reaction between Morita‐Baylis‐Hillman alcohols (MBHAs) and aryl triazenes. After thorough screening of the acids, nitric acid (HNO<sub>3</sub>) was unexpectedly found to be the most effective promoter for in situ generation of arenediazonium salts. This coupling reaction allows for a highly selective production of a various α‐arylmethyl β‐keto esters from readily accessible starting materials.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401386"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142989454","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
Controlled Synthesis of α‐Mono‐ and α,α‐Di‐Halogenated Ketones Through Coupling of Halogenated Diboromethanes with Carboxylic Acid Esters 卤化二硼甲烷与羧酸酯偶联合成α-单和α，α-二卤化酮
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401396
Chenxu Wu , Liangxuan Xu , Bowen Ren , Jianmei Lu , Chao Liu
{"title":"Controlled Synthesis of α‐Mono‐ and α,α‐Di‐Halogenated Ketones Through Coupling of Halogenated Diboromethanes with Carboxylic Acid Esters","authors":"Chenxu Wu ,&nbsp;Liangxuan Xu ,&nbsp;Bowen Ren ,&nbsp;Jianmei Lu ,&nbsp;Chao Liu","doi":"10.1002/ejoc.202401396","DOIUrl":"10.1002/ejoc.202401396","url":null,"abstract":"<div><div>Halogenated <em>gem</em>‐diboron reagents, as structurally unique <em>gem</em>‐diborylalkanes, are crucial in organic synthesis chemistry. Herein, we report a strategy with controlled synthesis of α‐mono‐ and α,α‐di‐halogenated ketones through nucleophilic addition reaction of halogenated diboromethanes with carboxylic acid esters. The substrate scope is broad and the nucleophilic addition reaction proceeds from a diverse range of carboxylic acid esters with bromo‐ or chloro‐diborylmethanes. Moreover, an intriguing heterocyclic compound has been serendipitously synthesized as well.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401396"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142967983","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
Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ2‐Isoxazolines via a Formal C(sp3)−H Functionalization 脱氢光氧化还原催化合成吲哚酰Δ2 -异恶唑啉的正式C(sp3) -H功能化。
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401369
Jonathan Da Luz , Farhaan Dobah , James A. Rossi‐Ashton , Richard J. Payne , William P. Unsworth , Wade F. Petersen
{"title":"Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ2‐Isoxazolines via a Formal C(sp3)−H Functionalization","authors":"Jonathan Da Luz ,&nbsp;Farhaan Dobah ,&nbsp;James A. Rossi‐Ashton ,&nbsp;Richard J. Payne ,&nbsp;William P. Unsworth ,&nbsp;Wade F. Petersen","doi":"10.1002/ejoc.202401369","DOIUrl":"10.1002/ejoc.202401369","url":null,"abstract":"<div><div>The discovery of a dehydrogenative photoredox catalyzed formal C(sp<sup>3</sup>)−H intramolecular cyclization of indolyl‐oximes to generate indolyl Δ<sup>2</sup>‐isoxazolines is reported. In contrast to the current state‐of‐the‐art, the reaction avoids the use of super stoichiometric chemical oxidants and high reaction temperatures and is proposed to operate via two sequential single electron oxidation events.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401369"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401369","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805190","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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