European Journal of Organic Chemistry最新文献

Tandem, Catalyst-Free C-C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-19 DOI: 10.1002/ejoc.202401108

Vasily Korochantsev, Artemy Fatkulin, Evgeniya Podyacheva, Alexander Boldyrev, Oleg Afanasyev, Denis Chusov

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Exploring the reactivity of (hetero)aryl amides in the Chan-Evans-Lam reaction with arylalkenyl boron reagents

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-18 DOI: 10.1002/ejoc.202400805

M. Manuel B. Marques, Joana R. M. Ferreira, Bruna F. L. Guerreiro, Fábio M. F. Santos, Samuel Guieu

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On the Halogenation of Tyrosine N-Oxime Methyl Ester

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-18 DOI: 10.1002/ejoc.202401153

Morgan Payne, Luke Fossatti, Stephen Chamberland

{"title":"On the Halogenation of Tyrosine N-Oxime Methyl Ester","authors":"Morgan Payne, Luke Fossatti, Stephen Chamberland","doi":"10.1002/ejoc.202401153","DOIUrl":"https://doi.org/10.1002/ejoc.202401153","url":null,"abstract":"Efficient syntheses of mono-, di-, and heterodihalogenated derivatives of tyrosine N-oxime methyl ester are reported. Monohalogenation with N-bromosuccinimide (NBS), N-chlorosuccinimide (NCS) or N-iodosuccinimide (NIS) was optimized by addition of acid to suppress dihalogenation, affording bromo, chloro, and iodo derivatives in 71%, 50-53%, and 78-80% yields, respectively. Homodihalogenation utilized a two-step, one-flask process via a spirocyclic intermediate, yielding dibromo, dichloro, and diiodo analogues, respectively (75-76%, 54-56%, 79-80%). This strategy was extended to synthesize heterodihalogenated bromochloro, bromoiodo, and chloroiodo derivatives from monohalogenated analogues (50-77%). Key to this approach was the formation of an oxidized spirocyclic intermediate using excess N-halosuccinimide, followed by Na₂S₂O₄ reduction. This method ensures complete conversion and simplifies purification. Nine halogenated building blocks were prepared. These methods provide practical access to versatile precursors for natural product synthesis and derivatization, offering potential for diverse synthetic applications including regioselective palladium-catalyzed couplings.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"227 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142670385","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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Xanthone Synthesis through Catalysis: Exploring the Green Limits of Homogeneous and Heterogeneous Methods 通过催化合成氧杂蒽酮：探索均相和异相方法的绿色极限

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1002/ejoc.202401027

Pamela Mendioroz, Andrés I. Casoni, María A. Volpe, Darío C. Gerbino

{"title":"Xanthone Synthesis through Catalysis: Exploring the Green Limits of Homogeneous and Heterogeneous Methods","authors":"Pamela Mendioroz, Andrés I. Casoni, María A. Volpe, Darío C. Gerbino","doi":"10.1002/ejoc.202401027","DOIUrl":"https://doi.org/10.1002/ejoc.202401027","url":null,"abstract":"The transition from traditional stoichiometric methods to catalytic processes has significantly advanced the synthesis of xanthones, privileged structures with diverse biological activities. This review critically examines various homogeneous and heterogeneous catalytic methodologies, emphasising their efficiency, and adherence to green chemistry principles. Through comparative analysis of key metrics such as Reaction Mass Efficiency (RME), Process Mass Intensity (PMI), E‐factor, and Turnover Number (TON), we highlight the superior performance of heterogeneous catalysts, which demonstrate high reusability, selectivity, and minimal waste generation. The choice of solvent, a crucial factor in the environmental footprint of these processes, is also assessed, focusing on greener alternatives. The robust nature and economic viability of heterogeneous catalysts make them ideal for large‐scale applications, offering suitable solutions for more environmentally‐friendly xanthone production. Furthermore, the reduction in byproducts and the importance of catalyst purity in pharmaceutical applications are discussed, underscoring the relevance of these advancements in meeting the rigorous standards of the industry. This review provides valuable insights into the ongoing evolution of catalytic strategies in xanthone synthesis, driving future developments in medicinal chemistry and green chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"123 1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637212","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: Continuous Flow Spirocyclization Reactions: Towards Efficient Synthesis of Chiral Spiropenicillanates (Eur. J. Org. Chem. 42/2024) 封面：连续流螺环化反应：实现手性螺青霉酸盐的高效合成（欧洲有机化学杂志 42/2024）

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-14 DOI: 10.1002/ejoc.202484201

Américo J. S. Alves, João A. D. Silvestre, Teresa M. V. D. Pinho e Melo

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Front Cover: Methanol-Mediated One-Pot Transformation of Benzonitriles to Five and Six-Membered Heterocycles: Synthesis and Mechanistic Approach (Eur. J. Org. Chem. 41/2024) 封面：甲醇介导的苯甲腈向五元和六元杂环的一锅转化：合成与机理方法（欧洲有机化学杂志 41/2024）

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-11 DOI: 10.1002/ejoc.202484101

Nikos Siakavaras, Michael G. Kallitsakis, Evangelos G. Bakalbassis, Michael M. Sigalas, Ioannis N. Lykakis

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Synthesis and EPR Studies of Zinc and Copper Tris(2‐pyridylmethyl)amines (TPMA) Metal Complexes Containing TEMPO Functionalities 含 TEMPO 功能的锌和铜三(2-吡啶基甲基)胺 (TPMA) 金属配合物的合成与 EPR 研究

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-11-11 DOI: 10.1002/ejoc.202400384

Elena Badetti , Vega Lloveras , Melvin Raulin , Francesca A. Scaramuzzo , Jaume Veciana , José Vidal‐Gancedo , Giulia Licini , Cristiano Zonta

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Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids 在合成氨基糖和多羟基联哌啶酸过程中稳定的 D-葡萄糖二硝酸盐

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400395

Rosalino Balo, Andrés Fernández, David Reza, Pablo López, George W. J. Fleet, Ramón J. Estévez, Juan C. Estévez

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I2-Promoted Povarov Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and N-Heteroaromatic Benzothiazoles I2 促进的 Povarov 多组分反应合成 2,2′-联喹啉和 N-杂芳香族苯并噻唑

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-10-02 DOI: 10.1002/ejoc.202400714

Yingying Zheng, Jie Li, Xiaotian Wu, Shanshan Ma, Xueyan Lv, Lei Feng, Qiang Han, Chen Ma

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Continuous Flow Spirocyclization Reactions: Towards Efficient Synthesis of Chiral Spiropenicillanates 连续流螺环化反应：实现手性螺青霉酸盐的高效合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2024-09-24 DOI: 10.1002/ejoc.202400689

Américo J. S. Alves, João A. D. Silvestre, Teresa M. V. D. Pinho e Melo

{"title":"Continuous Flow Spirocyclization Reactions: Towards Efficient Synthesis of Chiral Spiropenicillanates","authors":"Américo J. S. Alves, João A. D. Silvestre, Teresa M. V. D. Pinho e Melo","doi":"10.1002/ejoc.202400689","DOIUrl":"10.1002/ejoc.202400689","url":null,"abstract":"Herein, we describe the development of a continuous flow approach to chiral spiropenicillanates with remarkable bioactive properties from 6-alkylidenepenicillanates through phosphine-catalyzed [3+2] annulation of allenoates or 1,3-dipolar cycloaddition with diphenyldiazomethane. Model reactions were carried out using simple alkenes, such as methyl vinyl ketone and N-substituted maleimides, leading to the corresponding products in excellent yields (up to 96 %). The [3+2] annulation reaction was subsequently extended to the reactivity of 6-alkylidenepenicillanates, a more complex 2π-component with an exocyclic carbon-carbon double bond, allowing the synthesis of spirocyclic compounds. The 1,3-dipolar cycloaddition reactions between 6-alkylidenepenicillanates and diphenyldiazomethane under continuous flow conditions gave the corresponding spiro-1-pyrazolinepenicillanates in high yields (up to 81 %). Thermal ring contraction, via N2 extrusion, of spiro-1-pyrazolinepenicillanates under continuous flow conditions led to spirocyclopropanepenicillanates in quantitative yields. The continuous flow proved to be an efficient methodology for the synthesis of spiropenicillanates and represents a more sustainable approach for the larger-scale synthesis of spiropenicillanates with relevant biological activity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 42","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317745","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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