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Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles 通过吲哚噻唑的日光驱动光环化合成高荧光噻唑融合苯并[a]咔唑
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-20 DOI: 10.1002/ejoc.202400972
Prabhas Bhaumick, Nurabul Mondal, Lokman H. Choudhury
Herein we report for the first time a sunlight‐driven, irreversible photocyclization reaction of indole‐linked trisubstituted thiazoles, for the synthesis of highly fluorescent thiazole‐fused benzo[a]carbazoles using a mixture of solvents (CH3CN: DMSO; 3 : 1). Ring opening of indole moiety was observed in the case of thiazole derivatives having 2‐methyl indole substituents. Under similar reaction conditions, photocyclization of trisubstituted thiazoles having cyclic 1,3‐dicarbonyls in place of indole moiety also worked. This reaction provides products having two medicinally important moieties thiazole and benzocarbazoles. We have studied the photophysical properties of all the products and found that most of the synthesized products have very good fluorescence quantum yields.
在此,我们首次报道了吲哚连接的三取代噻唑在阳光驱动下的不可逆光环化反应,该反应使用混合溶剂(CH3CN: DMSO; 3 : 1)合成了高荧光噻唑融合苯并[a]咔唑。在具有 2-甲基吲哚取代基的噻唑衍生物中观察到了吲哚分子的开环。在类似的反应条件下,以环状 1,3-二羰基取代吲哚基的三取代噻唑的光环化反应也起作用。该反应提供了具有噻唑和苯并咔唑两种重要药用分子的产物。我们研究了所有产物的光物理特性,发现大多数合成产物都具有非常好的荧光量子产率。
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引用次数: 0
Tandem, Catalyst-Free C-C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite 亚磷酸钠与醛和氰乙酸甲酯串联、无催化剂 C-C 合成腈类化合物
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-19 DOI: 10.1002/ejoc.202401108
Vasily Korochantsev, Artemy Fatkulin, Evgeniya Podyacheva, Alexander Boldyrev, Oleg Afanasyev, Denis Chusov
Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C-C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepare multifunctional products. Knoevenagel reaction is one of the powerful tools to create carbon backbones of organic molecules; however, it requires subsequent reduction and/or decarboxylation to achieve a product with a saturated carbon chain. Herein we report a convenient one-step protocol for the reductive condensation between methyl cyanoacetate and aldehydes in the presence of stable, ecologically benign, cheap and available in bulk amounts sodium hypophosphite as a reductant. A description of both the reaction capabilities and limitations is given in this paper.
饱和碳链伸长是众多合成途径中的常见现象。虽然 C-C 单键的形成在有机合成中至关重要,但同时引入腈或酯等官能团可以合理地提高其实际效用,以制备多功能产品。Knoevenagel 反应是制造有机分子碳骨架的有力工具之一;然而,它需要后续的还原和/或脱羧反应才能得到具有饱和碳链的产物。在此,我们报告了在稳定、对生态无害、廉价且可大量获得的次磷酸钠作为还原剂的情况下,氰乙酸甲酯与醛之间一步还原缩合的简便方案。本文对该反应的能力和局限性进行了说明。
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引用次数: 0
Exploring the reactivity of (hetero)aryl amides in the Chan-Evans-Lam reaction with arylalkenyl boron reagents 探索(杂)芳基酰胺与芳基烯基硼试剂在 Chan-Evans-Lam 反应中的反应活性
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC 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
The unique reactivity and stability of enamides make them attractive reagents in organic synthesis. Herein, we investigated the reactivity of acetanilides and pyridyl acetamides in the formation of a C–N bond through a Chan-Evans-Lam reaction using arylalkenyl boron-based reagents yielding a wide scope of N-aryl enamides with an E configuration. The products obtained have been applied in the synthesis of N-heterocycles, an important scaffold in several biologically active compounds, via sequential Heck reaction to prove the practical utility of the prepared N-aryl enamides.
烯酰胺独特的反应活性和稳定性使其成为有机合成中极具吸引力的试剂。在此,我们研究了乙酰苯胺和吡啶基乙酰酰胺在使用芳基烯基硼基试剂通过 Chan-Evans-Lam 反应形成 C-N 键时的反应活性,得到了多种具有 E 构型的 N 芳基烯酰胺。所得到的产物通过连续的赫克反应被用于合成 N-杂环,这是多种生物活性化合物的重要支架,从而证明了所制备的 N-芳基烯酰胺的实用性。
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引用次数: 0
On the Halogenation of Tyrosine N-Oxime Methyl Ester 关于酪氨酸 N-肟甲酯的卤化反应
IF 2.8 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-18 DOI: 10.1002/ejoc.202401153
Morgan Payne, Luke Fossatti, Stephen Chamberland
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.
报告了酪氨酸 N-肟甲酯单卤、双卤和杂二卤衍生物的高效合成。使用 N-溴琥珀酰亚胺 (NBS)、N-氯琥珀酰亚胺 (NCS) 或 N-碘琥珀酰亚胺 (NIS)进行单卤化,通过加酸抑制二卤化进行优化,分别得到溴、氯和碘衍生物,收率分别为 71%、50-53% 和 78-80%。通过一个螺环中间体,采用两步一釜法进行同二卤化,分别得到二溴、二氯和二碘类似物(收率分别为 75-76%、54-56% 和 79-80%)。这一策略被扩展到从单卤代类似物合成杂二卤代溴氯、溴碘和氯碘衍生物(50-77%)。这种方法的关键是利用过量的 N-卤代丁二酰亚胺形成氧化的螺环中间体,然后用 Na₂S₂O₄ 还原。这种方法可确保完全转化并简化纯化过程。共制备出九种卤代结构单元。这些方法为天然产物合成和衍生化提供了实用的多功能前体,为包括区域选择性钯催化耦合在内的多种合成应用提供了潜力。
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引用次数: 0
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 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-15 DOI: 10.1002/ejoc.202401027
Pamela Mendioroz, Andrés I. Casoni, María A. Volpe, Darío C. Gerbino
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.
从传统的化学计量方法过渡到催化过程,极大地推动了具有多种生物活性的特殊结构--氧杂蒽酮的合成。本综述对各种均相和异相催化方法进行了批判性研究,强调了这些方法的效率以及对绿色化学原则的遵循。通过对反应质量效率 (RME)、过程质量强度 (PMI)、E 系数和周转次数 (TON) 等关键指标的比较分析,我们强调了异相催化剂的优越性能,这些催化剂具有高重复利用率、高选择性和最小废物产生量。溶剂的选择是这些工艺对环境影响的关键因素,我们也对溶剂的选择进行了评估,重点关注更环保的替代品。异相催化剂的稳健性和经济可行性使其成为大规模应用的理想选择,为更环保的氧杂蒽酮生产提供了合适的解决方案。此外,还讨论了减少副产品和催化剂纯度在制药应用中的重要性,强调了这些进展在满足行业严格标准方面的相关性。这篇综述为黄酮合成催化策略的不断发展提供了宝贵的见解,推动了药物化学和绿色化学的未来发展。
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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 Q2 CHEMISTRY, ORGANIC 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

The Front Cover illustrates the development of continuous flow spirocyclization of 6-alkylidenepenicillanates leading to chiral spiro-β-lactams through phosphine-catalyzed [3+2] annulation of allenoates and 1,3-dipolar cycloaddition with diphenyldiazomethane. The continuous-flow synthesis of spirocyclopropanepenicillanates through thermal ring contraction of spiro-1-pyrazolinepenicillanates was also included in the study. The reported methodology is a more sustainable approach for the scale-up production of compounds with significant biological properties in high yields. More information can be found in the Research Article by T. M. V. D. Pinho e Melo and co-workers (DOI: 10.1002/ejoc.202400689).

封面展示了 6-亚烷基青霉烷酸酯的连续流螺环化技术的发展,该技术通过磷化氢催化异烯酸酯的[3+2]环化反应以及与二苯基二氮甲烷的 1,3-二极环加成反应生成手性螺-β-内酰胺。该研究还包括通过螺-1-吡唑啉青霉烷酸酯的热环收缩连续流合成螺环丙青霉烷酸酯。所报告的方法是一种更可持续的方法,可用于扩大高产率生产具有重要生物特性的化合物。更多信息,请参阅 T. M. V. 的研究文章。V.D.Pinho e Melo 及其合作者的研究文章中(DOI: 10.1002/ejoc.202400689)。
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引用次数: 0
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 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-11-11 DOI: 10.1002/ejoc.202484101
Nikos Siakavaras, Michael G. Kallitsakis, Evangelos G. Bakalbassis, Michael M. Sigalas, Ioannis N. Lykakis

The Front Cover shows methanolic media as a vehicle for a green, one-pot and metal-free synthetic approach to 5- and 6-membered N-heterocycle clusters, starting with benzonitriles and different available diamines and amino alcohols. The dual role of methanol as solvent and as mediated agent is supported by mechanistic and theoretical studies. More information can be found in the Research Article by I. N. Lykakis and co-workers (DOI: 10.1002/ejoc.202400601).

封面展示了甲醇介质作为一种绿色、一锅式和无金属合成 5 元和 6 元 N-heterocycle 簇的载体,以苯腈和不同的二元胺和氨基醇为起点。机理和理论研究证实了甲醇作为溶剂和介导剂的双重作用。更多信息可参见 I. N. Lykakis 及其合作者的研究文章。Lykakis 及其合作者的研究文章中(DOI: 10.1002/ejoc.202400601)。
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引用次数: 0
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 Q2 CHEMISTRY, ORGANIC 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
A new family of stable radical‐containing polytopic ligands based on tris(2‐pyridylmethyl)amines TPMA architecture and their corresponding metal complexes have been synthesized. These molecular systems offered the possibility to investigate how various spin carriers, such as the metal ion and the organic radical, influence their EPR properties mainly through the empirical ratio of peak heights d1/d. Moreover, it has been possible to analyze how different conformations of TEMPO radical units in the molecular skeleton affect the metallic system.
我们合成了基于三(2-吡啶基甲基)胺 TPMA 结构的一系列新的稳定的含自由基多位配体及其相应的金属配合物。这些分子体系为研究金属离子和有机自由基等各种自旋载体如何主要通过峰高 d1/d 的经验比来影响其 EPR 特性提供了可能。此外,还可以分析分子骨架中 TEMPO 自由基单元的不同构象如何影响金属体系。
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引用次数: 0
Front Cover: N-Arylphenothiazines and N,N-Diarylphenazines as Tailored Organophotoredox Catalysts for the Reductive Activation of Alkenes (Eur. J. Org. Chem. 40/2024) 封面:N-Arylphenothiazines and N,N-Diarylphenazines as Tailored Organophotoredox Catalysts for the Reductive Activation of Alkenes (Eur. J. Org. Chem. 40/2024)
IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC Pub Date : 2024-10-24 DOI: 10.1002/ejoc.202484001
M. Sc. Madeleine Giraud, M. Sc. Mathis Robin Mitha, M. Sc. Sven Klehenz, Prof. Dr. Hans-Achim Wagenknecht

The Front Cover features an abstract representation of two novel, highly reducing organophotocatalysts derived from N-arylphenothiazines and N,N-diarylphenazines, compounds widely recognized as versatile and effective photoredox catalysts. The catalysts shown are the most efficient from a library of 17 catalysts synthesized. They show remarkable performance in the addition of methanol to α-methylstyrene, which was used as a model reaction, significantly reducing the reaction time and the catalyst loading by more than 20 times. Alongside the featured catalysts, the cover shows abstract representations of photophysical and photocatalytic concepts. The authors used spectroelectrochemistry and DFT calculations to further elucidate their findings and derive structure–activity relationships that might help to further improve organophotocatalysts. More information can be found in the Research Article by H.-A. Wagenknecht and co-workers (DOI: 10.1002/ejoc.202400847).

封面摘要介绍了两种新型高还原性有机光催化剂,它们分别来自 N-芳基吩噻嗪和 N,N-二芳基吩嗪,这两种化合物被广泛认为是多功能、高效的光氧化催化剂。图中展示的催化剂是从合成的 17 种催化剂库中最有效的催化剂。它们在甲醇与 α-甲基苯乙烯的加成反应中(该反应被用作模型反应)表现出卓越的性能,大大缩短了反应时间,催化剂负载量减少了 20 多倍。在介绍特色催化剂的同时,封面还抽象地展示了光物理和光催化概念。作者利用光谱电化学和 DFT 计算进一步阐明了他们的发现,并推导出结构-活性关系,这可能有助于进一步改进有机光催化剂。更多信息请参阅 H.-A. Wagenknecht 及其合作者的研究文章。Wagenknecht 及其合作者的研究文章中(DOI: 10.1002/ejoc.202400847)。
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引用次数: 0
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 Q2 CHEMISTRY, ORGANIC 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

A synthesis of the five membered iminosugar DAB and a divergent synthesis of the six membered iminosugar 1-dehydromannojirimycin (DMJ) and the corresponding sugar imino acid are reported. They involve double nucleophilic displacements of a D-xylose ditriflate by benzyl carbazate and a D-glucose ditriflate by allyl amine, respectively. They are followed by a similar protocol consisting of hydrolysis and oxidation or reduction of the resulting bicyclic glycosides. This allowed DMJ to be obtained from the cheap sugar D-glucose.

本研究报道了亚氨基糖 DAB 的合成以及 1-脱氢丹诺尻霉素(DMJ)和相应哌啶醇酸的歧化合成。关键步骤包括肼基羧酸苄酯和烯丙基胺分别对 D-木糖二呋喃酸酯和 D-葡萄糖二呋喃酸酯的双亲核置换。然后对生成的双环苷进行水解、氧化或还原。
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引用次数: 0
期刊
European Journal of Organic Chemistry
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