European Journal of Organic Chemistry最新文献

英文中文

Synthetic Strategies to Access Fluorinated Azoles 获取氟化唑的合成策略

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-15 DOI: 10.1002/ejoc.202500508

Mohammed K. Abd El‐Gaber , Mario Djugovski , Tzu‐Yu Huang , Sweta Adhikari , Sudeshna Roy

Incorporating fluorine into azoles is not only a common practice but also an essential tactic in medicinal chemistry, due to their ability to fine‐tune a molecule's physicochemical, pharmacokinetic, and pharmacodynamic profiles. The strategic introduction of fluorine into nitrogen‐containing five‐membered heterocycles can significantly enhance metabolic stability, membrane permeability, and binding affinity—key factors in modern drug development. This review provides an up‐to‐date overview of key synthetic strategies for monofluorination, difluoromethylation, and trifluoromethylation across 11 prominent azoles: 1,2,3‐triazoles, 1,2,4‐triazoles, tetrazoles, pyrazoles, imidazoles, pyrroles, isoxazoles, oxazoles, thiazoles, thiadiazoles, and isothiazoles. This review aims to identify current limitations in the field and delineate existing research gaps that present further opportunities for innovation in these domains, which are essential for propelling pharmaceutical and biomedical research. By integrating new synthetic advancements and diverse strategies to access them, this review aims to serve as both a practical guide and a source of inspiration for chemists exploring the next generation of fluorinated azole pharmaceuticals.

将氟加入到唑中不仅是一种常见的做法，而且是药物化学中的一种基本策略，因为它们能够微调分子的物理化学、药代动力学和药效学特征。在含氮五元杂环中引入氟可以显著提高代谢稳定性、膜通透性和结合亲和力，这是现代药物开发中的关键因素。这篇综述提供了最新的单氟化、二氟甲基化和三氟甲基化合成策略的概述，涉及11种主要的唑类：1,2,3 -三唑、1,2,4 -三唑、四唑、吡唑、咪唑、吡咯、异恶唑、恶唑、噻唑、噻二唑和异噻唑。本综述旨在确定该领域目前的局限性，并描述现有的研究差距，这些研究差距为这些领域的进一步创新提供了机会，这对推动制药和生物医学研究至关重要。通过整合新的合成进展和不同的策略来获取它们，本综述旨在为化学家探索下一代氟化唑药物提供实用指南和灵感来源。

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引用次数: 0

Defective NiO Nanoparticles Supported on Nb2O5 for Solid‐Catalyzed Markovnikov‐Selective Hydroboration of Styrenes n2o5负载的缺陷NiO纳米颗粒用于固体催化苯乙烯的Markovnikov选择性硼氢化反应

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-15 DOI: 10.1002/ejoc.202500824

Ayako Taketoshi , Yusei Kimura , Eiji Hirano , Norihito Sakaguchi , Tamao Ishida , Toru Murayama , Yoshitaka Yamaguchi

Markovnikov selective hydroboration of alkenes with an air‐ and moisture‐stable diboron reagent is a more challenging reaction than the anti‐Markovnikov‐selective one. We report that nickel oxide (NiO) supported on niobium pentoxide (Nb₂O₅) efficiently catalyzed the hydroboration of 4‐tert‐butylstyrene, affording a Markovnikov (branched) adduct with excellent selectivity. To the best of our knowledge, this is the first report of the Markovnikov‐selective hydroboration of styrenes with a diboron reagent, bis(pinacolato)diboron, using a solid catalyst. NiO on Nb₂O₅ contains Ni³⁺, which is more catalytically active than Ni²⁺, as a major species in contrast to bulk NiO. However, the catalytic activity decreased upon recycling tests because the Ni species leached from NiO/Nb₂O₅. The catalytically active species were NiO on Nb₂O₅ and leached Ni species. To improve the reusability of the catalyst system, NiO/Nb₂O₅, ZnO was introduced as a redeposition site for the leached Ni species. Ultimately, the desired Markovnikov adduct was obtained in high yield and selectivity using NiO/Nb₂O₅ in the presence of ZnO (92% yield and 92% selectivity), and catalyst reusability was also improved.

用空气和水分稳定的二硼试剂进行烯烃的马尔可夫尼科夫选择性硼化反应是一个比反马尔可夫尼科夫选择性反应更具挑战性的反应。我们报道了负载在五氧化二铌上的氧化镍（NiO）有效地催化了4叔丁基苯乙烯的硼氢化反应，得到了具有优异选择性的Markovnikov（支链）加合物。据我们所知，这是使用固体催化剂，用二硼试剂双（pinacolato）二硼对苯乙烯进行马尔可夫尼科夫选择性硼化反应的第一篇报道。NiO中含有ni3 +，与ni2 +相比，ni3 +的催化活性更强。然而，在回收试验中，由于镍从NiO/Nb 2o中浸出，催化活性下降。催化活性物质为n2o5上的NiO和浸出的Ni。为了提高催化剂体系的可重复使用性，引入NiO/Nb 2o5， ZnO作为浸出镍的再沉积位点。最终，在ZnO存在下，以NiO/Nb 2o5为原料，以92%的产率和92%的选择性，获得了高收率、高选择性的Markovnikov加合物，并提高了催化剂的可重复使用性。

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引用次数: 0

Naphthalene Diimide‐Based Small‐Molecule Semiconductors Enabling Air‐Stable n‐Type Organic Field‐Effect Transistors 基于萘二亚胺的小分子半导体，实现空气稳定的n型有机场效应晶体管

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-15 DOI: 10.1002/ejoc.202500864

Zhaohan Ding , Xiang Sun , Yu‐Dong Zhao , Defeng Cui , Junmei Hu , Wei‐Chen Gao , Ben Fan , Jing Qiao , Ying‐Shi Guan

The development of ambient‐stable n‐type organic semiconductors is a critical yet challenging research frontier. Herein, we report a rational molecular design by functionalizing naphthalene diimide (NDI) cores with strong electron‐withdrawing termini via thiophene bridges. Density functional theory calculations revealed enhanced planarity and significantly lowered lowest unoccupied molecular orbitals energy level (<−4.1 eV), which were corroborated by photophysical and electrochemical analyses. The solution‐processed organic field‐effect transistors (OFETs) demonstrated electron mobilities over 10⁻³cm²V⁻¹s⁻¹, all of which were fabricated and measured under ambient conditions. Remarkably, the devices retained >97% performance after 2‐week storage in ambient conditions. Furthermore, to evaluate the potential of the semiconductors for flexible electronics applications, we fabricated flexible OFETs by integrating the self‐assembled NDI‐4X (X = F, Cl) thin films prepared via air‐water interfacial self‐assembly. Also under ambient conditions, the devices exhibited higher electron mobilities of 4.49 × 10⁻³ (NDI‐4F) and 7.21 × 10⁻³cm²V⁻¹s⁻¹(NDI‐4Cl) than their halogen‐free counterpart NDI‐4H (1.14 × 10⁻³cm²V⁻¹s⁻¹). This work demonstrates that introducing strong electron‐withdrawing groups at both ends of electron‐deficient units provides an effective pathway to achieve ambient‐stable n‐type small‐molecule semiconductors, thereby enabling their application in next‐generation, ambient‐operating flexible organic electronics.

环境稳定n型有机半导体的发展是一个关键而又具有挑战性的研究前沿。在此，我们报告了一种合理的分子设计，通过噻吩桥将具有强吸电子末端的萘二亚胺（NDI）核功能化。密度泛函理论计算结果表明，该材料的平面性增强，最低未占据分子轨道能级（<−4.1 eV）显著降低，光物理和电化学分析也证实了这一点。溶液处理的有机场效应晶体管（ofet）的电子迁移率超过10−3 cm 2 V−1 s−1，所有这些都是在环境条件下制造和测量的。值得注意的是，这些器件在环境条件下存储两周后仍保持了97%的性能。此外，为了评估柔性电子应用半导体的潜力，我们通过集成通过空气-水界面自组装制备的自组装NDI - 4X （X = F, Cl）薄膜来制造柔性ofet。同样，在环境条件下，器件的电子迁移率为4.49 × 10−3 （NDI‐4F）和7.21 × 10−3 cm 2v−1 s−1 (NDI‐4Cl)，高于无卤NDI‐4H （1.14 × 10−3 cm 2v−1 s−1）。这项工作表明，在缺电子单元的两端引入强吸电子基团，为实现环境稳定的n型小分子半导体提供了有效途径，从而使其能够应用于下一代环境可操作的柔性有机电子产品。

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引用次数: 0

Front Cover: Discovery of Some New Heterocyclic Systems from Carbene-Based Reactions of Indigo and N-Methyl Derivatives (Eur. J. Org. Chem. 46/2025) 封面：从靛蓝和n -甲基衍生物的碳基反应中发现一些新的杂环体系。j . Org。化学46/2025)

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-12 DOI: 10.1002/ejoc.70217

Sarfaraz Ali Ghumro, Matthew J. Perry, Christopher Richardson, Stephen G. Pyne, John B. Bremner, Paul A. Keller

The Front Cover captures the blue sky nature of research with the indigo skeleton serving as a springboard into the unknown, where unprecedented heterocyclic structures were discovered via the addition ofcarbenes or rhodium carbenoids. More information can be found in the Research Article by J. B. Bremner, P. A. Keller and co-workers (DOI: 10.1002/ejoc.202500525). We gratefully acknowledge Dr. Ronald Brown (School of Science, University of Wollongong) for generating the cover art with help from the author Sarfaraz Ali, using a photograph taken by Susan Bremner in the Wollongong area.

封面捕捉了研究的蓝天性质，靛蓝骨架作为进入未知领域的跳板，在那里通过添加碳烯或类碳铑发现了前所未有的杂环结构。更多信息可以在J. B. Bremner， P. A. Keller及其同事的研究文章中找到（DOI: 10.1002/ejoc.202500525）。我们非常感谢Ronald Brown博士（卧龙岗大学理学院）在作者Sarfaraz Ali的帮助下创作了封面，使用了Susan Bremner在卧龙岗地区拍摄的照片。

引用次数: 0

Blue‐Light‐Induced Pd‐Catalyzed Quinolinamide‐Directed Regioselective C‐8 Benzylation of 1‐Naphthylamines Using Flow‐Generated Aryldiazomethanes in Batch and Continuous‐Flow 蓝光诱导pd催化喹啉酰胺定向区域选择性C-8甲基化1-萘胺的间歇和连续流合成芳基重氮甲烷

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-10 DOI: 10.1002/ejoc.202500849

Wei Zhang , Yanxin Xie , Zaikun Xue , Changqing Miao , Jiao Guo , Baoli Zhao

Herein, a continuous photo‐flow protocol for quinolinamide‐directed regioselective C‐8 benzylation of 1‐naphthylamine derivatives via CH bond functionalization with flow‐generated aryldiazomethanes is reported. A wide range of 8‐benzylated‐1‐naphthylamide products are afforded in satisfactory yields upon palladium catalysis via a bidentate directing process under illumination by 12 W blue light‐emitting diodes (450 nm). This mild, simple, and convenient synthetic method allows a wide range of easily handled aryl aldehydes, without the exclusion of either moisture or oxygen. This transformation is environmentally friendly and operationally simple, and it can be easily scaled up to the gram scale with good selectivity. Finally, an improved protocol for CH functionalization is described, which relies on the use of a continuous‐flow photo‐microreactor.

本文报道了一种连续光流方法，通过流动产生的芳基重氮甲烷的C- H键功能化，喹啉酰胺定向的1-萘胺衍生物的区域选择性C-8苄基化。在12w蓝光发光二极管（450nm）的照明下，通过双齿定向工艺钯催化，可获得多种8-苄基化-1-萘酰胺产品，产率令人满意。这种温和，简单，方便的合成方法允许广泛的易于处理的芳基醛，而不排除水分或氧气。这种转化对环境友好，操作简单，并且可以很容易地扩大到克尺度，具有良好的选择性。最后，描述了C - H功能化的改进协议，该协议依赖于连续流光微反应器的使用。

引用次数: 0

Salt‐Free CatAnionic Vesicular Nanoreactor from Dithiocarbamate: Michael Addition of Nitroolefins in Water 二硫代氨基甲酸盐制备的无盐阳离子囊状纳米反应器：Michael

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-10 DOI: 10.1002/ejoc.202500770

Panassilp Authai , Witsanu Sombat , Voravee P. Hoven , Tirayut Vilaivan , Panuwat Padungros

The salt‐free CatAnionic vesicle is previously generated by mixing cationic and anionic amphiphiles and removing the salt that occurred as a byproduct from the mixture. In this study, a new strategy to produce the salt‐free CatAnionic vesicle of N,N‐dialkylammonium N,N‐dialkyldithiocarbamate (AmDTC) is reported through a one‐step condensation between secondary amine and CS₂. The AmDTC dispersed in water, resulting in the spontaneous formation of salt‐free CatAnionic vesicles. Among several AmDTCs, the N,N‐didodecylammonium N,N‐didodecyldithiocarbamate (AmDTC‐C12) showed high stability and is applied as a vesicular nanoreactor for the Michael addition in water. These vesicles catalyzed aqueous Michael additions of nitroolefins, affording 23 adducts in 65%–92% yields. The vesicles enabled preparative‐scale and one‐pot Michael addition by in situ generation of AmDTC‐C12 vesicle afforded the Michael adducts also in good yields. The AmDTC‐C12 vesicular nanoreactor is applied for the synthesis of (±)‐baclofen with 54% yields over three steps. Reusability of the AmDTC‐C12 is demonstrated and allowed the reuse up to seven cycles. Finally, chemical recycling of N,N‐didodecylamine precursor is demonstrated by converting AmDTC‐C12 to N,N‐didodecylammonium chloride salt by simple acidification. Owing to their simple precursors and mild synthesis, salt‐free CatAnionic vesicles from AmDTC show promising and untapped potentials as organocatalysts and delivery applications.

无盐的cat阴离子囊泡是通过混合阳离子和阴离子两亲体并去除混合物中作为副产物的盐而产生的。本文报道了一种通过仲胺与cs2一步缩合制备N， N -二烷基二硫代氨基甲酸铵（AmDTC）无盐阳离子囊泡的新策略。AmDTC分散在水中，导致自发形成无盐的catanonic囊泡。在几种AmDTC中，N， N -二十二烷基铵N， N -二十二烷基二硫代氨基甲酸酯（AmDTC - C12）表现出较高的稳定性，并作为囊状纳米反应器应用于水中的Michael加成。这些囊泡催化了硝基烯烃的水溶液加成，得到23种加合物，产率为65% ~ 92%。通过原位生成AmDTC - C12囊泡，该囊泡实现了制备规模和一锅Michael加成，也获得了高产量的Michael加合物。AmDTC - C12囊状纳米反应器用于合成（±）-巴氯芬，三步合成收率为54%。演示了AmDTC - C12的可重用性，并允许重复使用多达七个周期。最后，通过简单酸化将AmDTC - C12转化为N， N‐二十二烷基氯化铵盐，证明了N， N‐二十二烷基胺前体的化学回收。由于其简单的前体和温和的合成，来自AmDTC的无盐cat阴离子囊泡作为有机催化剂和递送应用具有广阔的潜力。

{"title":"Salt‐Free CatAnionic Vesicular Nanoreactor from Dithiocarbamate: Michael Addition of Nitroolefins in Water","authors":"Panassilp Authai , Witsanu Sombat , Voravee P. Hoven , Tirayut Vilaivan , Panuwat Padungros","doi":"10.1002/ejoc.202500770","DOIUrl":"10.1002/ejoc.202500770","url":null,"abstract":"<div><div>The salt‐free CatAnionic vesicle is previously generated by mixing cationic and anionic amphiphiles and removing the salt that occurred as a byproduct from the mixture. In this study, a new strategy to produce the salt‐free CatAnionic vesicle of <em>N</em>,<em>N</em>‐dialkylammonium <em>N</em>,<em>N</em>‐dialkyldithiocarbamate (AmDTC) is reported through a one‐step condensation between secondary amine and CS<sub>2</sub>. The AmDTC dispersed in water, resulting in the spontaneous formation of salt‐free CatAnionic vesicles. Among several AmDTCs, the <em>N</em>,<em>N</em>‐didodecylammonium <em>N</em>,<em>N</em>‐didodecyldithiocarbamate (<strong>AmDTC‐C12</strong>) showed high stability and is applied as a vesicular nanoreactor for the Michael addition in water. These vesicles catalyzed aqueous Michael additions of nitroolefins, affording 23 adducts in 65%–92% yields. The vesicles enabled preparative‐scale and one‐pot Michael addition by in situ generation of <strong>AmDTC‐C12</strong> vesicle afforded the Michael adducts also in good yields. The <strong>AmDTC‐C12</strong> vesicular nanoreactor is applied for the synthesis of (±)‐baclofen with 54% yields over three steps. Reusability of the <strong>AmDTC‐C12</strong> is demonstrated and allowed the reuse up to seven cycles. Finally, chemical recycling of <em>N</em>,<em>N</em>‐didodecylamine precursor is demonstrated by converting <strong>AmDTC‐C12</strong> to <em>N</em>,<em>N</em>‐didodecylammonium chloride salt by simple acidification. Owing to their simple precursors and mild synthesis, salt‐free CatAnionic vesicles from AmDTC show promising and untapped potentials as organocatalysts and delivery applications.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 45","pages":"Article e202500770"},"PeriodicalIF":2.7,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145381823","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

Modular Synthesis of 3,4‐Disubstituted Pyrroles Through Three‐Component Van Leusen Reaction of Propargylamines with Tosylmethyl Isocyanide and Water 丙胺与异氰酸甲酯及水的三组分Van Leusen反应模块化合成3,4-二取代吡咯

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-10 DOI: 10.1002/ejoc.202500855

Binbin Fei , Yangzilin Kong , Yanan Liu , Ni Gu , Qiang Tang , Yongjia Shang , Xinwei He

A novel three‐component van Leusen strategy has been developed for the efficient and straightforward synthesis of valuable 3,4‐disubstituted pyrroles from easily available propargylamines, tosylmethyl isocyanide, and water. This transformation advances through the formation of a pyrrole framework via [3 + 2] cycloaddition with tosylmethyl isocyanide and a sequential nucleophilic substitution, ring‐opening, and deprotonation/protonation cascade process. This reaction provides a convenient modular access to pyrrole derivatives with aryl and benzoyl groups through the formation of three new bonds and one heterocycle from readily available acyclic precursors in a single step.

一种新的三组分van Leusen策略已经被开发出来，用于从容易获得的丙胺、甲苯基甲基异氰化物和水中高效、直接地合成有价值的3,4-二取代吡咯。这种转化通过与异氰酸甲酯[3 + 2]环加成形成吡咯骨架和顺序亲核取代、开环和去质子化/质子化级联过程进行。该反应提供了一个方便的模块化途径，通过在一个步骤中从现成的无环前体形成三个新的键和一个杂环，得到具有芳基和苯甲酰基的吡咯衍生物。

引用次数: 0

Transition‐Metal‐Catalyzed Convergent Synthesis of Heterocyclic Compounds via CH Activation/Cyclization: An Overview and Summary Toward Terminal Alkynes 过渡金属催化C?聚合合成杂环化合物H活化/环化：末端炔的综述与总结

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-10 DOI: 10.1002/ejoc.202500651

Fen Xu , Zi‐Han Wang , Meng‐Yu Sun , Luciano Barboni , Yuan Feng , Huan‐Huan Zhao , Yang Yang , Fan‐Wang Zeng

The development of one‐step transformations to heterocyclic compounds would considerably boost the synthetic efficiency in organic chemistry. In recent years, numerous examples of the transition‐metal‐catalyzed (TMC) CH activation/annulation strategy have been reported. Despite remarkable progress achieved with internal alkynes, allenes, and alkyne surrogates, terminal alkynes remain challenging substrates. Due to their relatively acidic terminal protons, terminal alkynes easily undergo alternative homocoupling reactions under commonly used oxidative conditions, exhibiting significant difficulties in CH functionalizations. To date, the CH activation involving terminal alkynes remains one of the most promising and appealing areas in organic synthesis. This review provides a comprehensive overview of the current progress in tandem CH activation reactions with terminal alkynes. With a strong emphasis on the catalysis of Rh and Co transition metals, it predominantly covers the synthesis of five‐, six‐membered heterocycles, and fused heterocycles. In this protocol, specific topics, such as purely chemical synthesis, electrochemical synthesis, and enantioselective synthesis, mechanistic details associated with the documented reactions are discussed. In addition, a tactical user guidance for terminal alkynes‐participated CH activation is also put forward.

一步法转化成杂环化合物的发展将大大提高有机化学的合成效率。近年来，已经报道了许多过渡金属催化（TMC） C - H活化/环化策略的例子。尽管在内炔、烯和炔代物方面取得了显著进展，但末端炔仍然是具有挑战性的底物。由于末端质子相对酸性，末端炔在常用的氧化条件下容易发生选择性均偶联反应，在C - H官能化中表现出明显的困难。迄今为止，涉及末端炔的C - H活化仍然是有机合成中最有前途和最吸引人的领域之一。本文综述了末端炔烃串联C - H活化反应的研究进展。重点关注Rh和Co过渡金属的催化作用，主要涉及五元、六元杂环和熔融杂环的合成。在本协议中，具体的主题，如纯化学合成，电化学合成，和对映选择性合成，机理细节与记录的反应进行了讨论。此外，还提出了终端炔参与C - H激活的战术用户指南。

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引用次数: 0

A Practical and Scalable Synthesis of Cyclized and Uncyclized Xanthene‐1,8‐Dione Derivatives Using Cyanuric Chloride as a Green Organocatalyst 以三聚氰胺为绿色有机催化剂合成环化和非环化杂蒽- 1,8 -二酮衍生物

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-10 DOI: 10.1002/ejoc.202500921

Pooja Sivaganesan , Ghanashyam Sivaprasad , Diksha Bansal , Mrinal Kanti Das , Saikat Chaudhuri

A mild, water‐mediated protocol has been developed for the synthesis of both uncyclized and cyclized 1,8‐dioxo‐octahydroxanthene derivatives under ambient conditions. Utilizing cyclic‐1,3‐dicarbonyl compounds and structurally diverse aromatic or heteroaromatic aldehydes, the transformation proceeds efficiently with cyanuric chloride (TCT) as a green organocatalyst. The reaction conditions are finely tunable, allowing selective access to either uncyclized intermediates or cyclized products by adjusting time and temperature, thereby enabling modular control over product outcomes. The protocol also demonstrates excellent compatibility with isatin derivatives, yielding spirooxindolo xanthenedione frameworks in high yields. Substrate scope evaluation revealed broad functional group tolerance, with several products displaying notable biological activities, including anticancer, antibacterial, and antileishmanial properties. All synthesized compounds are fully characterized using spectroscopic techniques such as ¹H, ¹³C, and mass spectroscopy. A detailed, plausible mechanism for the transformation has also been proposed and discussed. Comprehensive green metrics, including atom economy, E‐factor, process mass intensity, and other metrics, are calculated for each cyclized derivative. Gram‐scale experiments further confirmed the scalability and environmental sustainability of this operationally simple, metal‐free, and energy‐efficient protocol.

一种温和的、水介导的方案已经被开发用于在环境条件下合成非环化和环化1,8 -二氧八羟基蒽衍生物。利用环- 1,3 -二羰基化合物和结构多样的芳香或杂芳香醛，以三聚氰胺（TCT）作为绿色有机催化剂，有效地进行转化。反应条件是精细可调的，允许通过调节时间和温度选择性地进入非环化中间体或环化产物，从而实现对产品结果的模块化控制。该方案还证明了与isatin衍生物的良好相容性，产率高的spirooxindolo杂蒽二酮框架。底物范围评价显示广泛的功能基团耐受性，一些产品显示出显著的生物活性，包括抗癌、抗菌和抗利什曼原虫的特性。所有合成的化合物都使用光谱技术，如1h， 13c和质谱进行了充分的表征。本文还提出并讨论了一种详细的、合理的转化机制。综合绿色指标，包括原子经济，E因子，过程质量强度，和其他指标，计算每个环化衍生物。克尺度的实验进一步证实了这种操作简单、无金属、节能的方案的可扩展性和环境可持续性。

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引用次数: 0

Visible‐Light‐Induced Cyclization of Vinyl Isocyanides with Diaryl Disulfides/1,2‐Dialkyldiselanes for the Synthesis of 1‐Substituted Isoquinolines 乙烯基异氰酸酯与二芳基二硫化物/1,2 -二烷基二烷的可见光诱导环化合成1 -取代异喹啉

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-12-10 DOI: 10.1002/ejoc.202500715

Yong‐Xin Liang , Qing‐Wen Ai , Xue‐Cen Xu , Yu‐Long Zhao

Isoquinoline compounds, especially 1‐substituted derivatives, have garnered considerable attention due to their ubiquitous presence in natural products and pharmaceuticals. Herein, a novel visible‐light‐induced tandem cyclization of vinyl isocyanides with diaryl disulfides or 1,2‐dialkyldiselanes has been developed. The reaction tolerates a wide range of substrates and provides an environmentally friendly route to the synthesis of 1‐thio/selenoisoquinolines from the easily available starting materials in a single step.

异喹啉类化合物，尤其是1 -取代衍生物，由于其在天然产物和药物中的普遍存在而引起了相当大的关注。本文提出了一种新的可见光诱导的乙烯基异氰酸酯与二硫化物或1,2 -二烷基二烷的串联环化反应。该反应可耐受多种底物，并为从易于获得的原料中一步合成1 -硫代/硒代异喹啉提供了一种环保的途径。

引用次数: 0

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