European Journal of Organic Chemistry最新文献_第2页

1,2‐Sulfonylative‐Arylation of Acrylamides via Strain‐Release‐/Aromaticity‐Driven Radical Generation and SO2‐Capture under Photoredox Catalysis to Access S(VI)‐Oxindoles 在光氧化还原催化下，通过菌株释放/芳香性驱动自由基生成和SO2捕获获得S(VI) -氧吲哚的丙烯酰胺1,2 -磺酰化-芳基化

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-07 DOI: 10.1002/ejoc.202500726

Abhaykumar Vishwakarma, Tonish Kumar Sahu, Shanti Gopal Patra, Chhanda Paul, Somalisa Behera, Sanjeeb Sahoo, Tabrez Khan

{"title":"1,2‐Sulfonylative‐Arylation of Acrylamides via Strain‐Release‐/Aromaticity‐Driven Radical Generation and SO2‐Capture under Photoredox Catalysis to Access S(VI)‐Oxindoles","authors":"Abhaykumar Vishwakarma, Tonish Kumar Sahu, Shanti Gopal Patra, Chhanda Paul, Somalisa Behera, Sanjeeb Sahoo, Tabrez Khan","doi":"10.1002/ejoc.202500726","DOIUrl":"https://doi.org/10.1002/ejoc.202500726","url":null,"abstract":"γ‐Keto sulfones, despite being a medicinally relevant building block, have never been integrated with the bioactive oxindole scaffold present in several alkaloid natural products. On the other hand, strategies involving SO2 capture in organic molecules to access value‐added products are gaining momentum. Therefore, a strategy en route to γ‐keto alkylsulfonylated oxindoles bearing a β‐all‐carbon quaternary center is disclosed. Toward this goal, the bisfunctionalization of N‐(hetero)arylacrylamides has been realized via the strain‐release driven ring‐scission of strained 3°‐cyclopropanols in the presence of DABSO under visible‐light photoredox catalysis to access a library of γ‐keto alkylsulfonylated oxindoles. Also, the aromaticity‐driven bond‐scission in pro‐aromatics like 4‐alkyl‐1,4‐DHPs in the presence of Na2S2O5 under visible‐light photoredox catalysis has been exploited to trigger the alkylsulfonylative‐arylation of N‐(hetero)arylacrylamides to access a library of alkylsulfonylated oxindoles featuring a β‐all‐carbon quaternary center. Broad substrate scope is demonstrated, and the mechanistic probing studies have been complemented with DFT calculations. Also, moderate to potent cytotoxic activity is observed against the tested triple‐negative breast cancer cell lines for some of the synthesized sulfonylated oxindole derivatives. Further, evaluation of the mechanism of cell death for the most potent oxindole analog revealed that it induces apoptosis in a concentration‐dependent manner.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145235389","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

A Density Functional Theory‐Genetic Algorithm Approach for the Structural Elucidation of Linear Diamantane Polyesters and their Nonlinear Optical Properties 用密度泛函理论-遗传算法研究线性金刚石烷聚酯的结构及其非线性光学性质

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-07 DOI: 10.1002/ejoc.202500645

Saravanan Gowrisankar, Marius Lang, Steffen Schröder, Neeshma Mathew, Jörn Schmedt auf der Günne, Peter R. Schreiner

{"title":"A Density Functional Theory‐Genetic Algorithm Approach for the Structural Elucidation of Linear Diamantane Polyesters and their Nonlinear Optical Properties","authors":"Saravanan Gowrisankar, Marius Lang, Steffen Schröder, Neeshma Mathew, Jörn Schmedt auf der Günne, Peter R. Schreiner","doi":"10.1002/ejoc.202500645","DOIUrl":"https://doi.org/10.1002/ejoc.202500645","url":null,"abstract":"We report a series of diamantane polyesters synthesized as head‐to‐head and side‐to‐side linear chain polymers. The incorporation of the bulky and rigid diamantyl moiety significantly enhances the thermal stabilities of these polymers compared to well‐established linear aliphatic polyesters, such as poly(ε‐caprolactone), poly(lactic acid), poly(butylene succinate), and poly(glycolic acid). This enhancement is confirmed by thermogravimetric analyzes, which show degradation onsets in the range of 520 to 580 °C. The structural characterization of these polyesters posed significant challenges due to virtual insolubility in organic solvents, limiting the use of techniques such as mass spectrometry and liquid‐state nuclear magnetic resonance (NMR) spectroscopy. To address these challenges, a genetic algorithm for structure prediction based on periodic density functional theory computations was employed, yielding a structure that closely matches the powder X‐ray diffraction data. Heavily constrained Rietveld refinement provided excellent agreement with the experimental results. These findings, combined with solid‐state NMR data, have been integrated to provide a comprehensive understanding of the polyester properties. These polyesters demonstrate promising nonlinear optical responses, including white‐light emission upon continuous infrared laser irradiation, making them candidates for optoelectronic applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"50 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145235390","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

A New Methodology for Preparing Benzylated Aminopyridines Yields Previously Inaccessible Organocatalysts 一种制备苯基化氨基吡啶的新方法产生了以前难以获得的有机催化剂

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-06 DOI: 10.1002/ejoc.202500749

Mikhail Kozlov, Fatma Saady, Or Fleischer, Shai Ben Sasson, Ibrahim Amer, Scott J. Miller, Moshe Portnoy

引用次数: 0

A Family of Methylene‐Bridged Fully Functionalized Polynitroarenes and Tetrazole‐Based Energetic Materials 一类亚甲基桥接全功能化聚硝基芳烃和四唑基含能材料

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-04 DOI: 10.1002/ejoc.202500823

Amit Bijlwan, Priyanka Das, Prachi Bhatia, Vikas D. Ghule, Dheeraj Kumar

{"title":"A Family of Methylene‐Bridged Fully Functionalized Polynitroarenes and Tetrazole‐Based Energetic Materials","authors":"Amit Bijlwan, Priyanka Das, Prachi Bhatia, Vikas D. Ghule, Dheeraj Kumar","doi":"10.1002/ejoc.202500823","DOIUrl":"https://doi.org/10.1002/ejoc.202500823","url":null,"abstract":"Herein, to fine‐tune the energetic properties of 2,4,6‐trinitrobenzene‐1,3‐diamine/diol, these are combined with tetrazole via a methylene bridge. This strategy unlocks the tunability of polynitroarenes performances via salt formation, which is restricted in directly CN connected polynitroarenes and azole derivatives. The amino/hydroxy functionalities between the nitro groups on the benzene ring provide extensive inter‐ and intramolecular hydrogen bonding interactions, contributing to improved stability, whereas the tetrazole ring increases the nitrogen percentage and energetic performance. Due to the presence of one and three labile protons in the amino derivative (compounds 4) and hydroxy derivative (compounds 5), respectively, a series of mono‐ and tricationic salts are prepared to further fine‐tune the overall performances. Among all the synthesized compounds, the tricationic energetic salt 10 (Dv = 8135 m s−1, IS > 40 J) exhibits energetic performance comparable to TATB and is insensitive. All the compounds are characterized through infrared spectroscopy, Nuclear Magnetic Resonance (NMR) spectroscopy, differential scanning calorimetry, elemental analysis, and high‐resolution mass spectra studies. The relationship between structure and properties is further explored using Hirshfeld surface, noncovalent interaction, Localized Orbital Locator (LOL)‐π, and electrostatic potential analysis.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145215988","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

Iron‐Doped Hydrotalcite: A Heterogeneous Catalyst for the Selective Synthesis of 2‐Substituted Benzimidazoles and Benzothiazoles Using Alcohols and Solvent‐Free Reaction Conditions 铁掺杂水滑石：在醇和无溶剂条件下选择性合成2取代苯并咪唑和苯并噻唑的非均相催化剂

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-04 DOI: 10.1002/ejoc.202500759

Pooja Devi Bora, Yabon Pame, Ramen Jamatia

引用次数: 0

The Nonlinear Optical Behavior of Linear Diamantane Polyamides 线性Diamantane聚酰胺的非线性光学行为

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-04 DOI: 10.1002/ejoc.202500643

Saravanan Gowrisankar, Marius Lang, Peter R. Schreiner

{"title":"The Nonlinear Optical Behavior of Linear Diamantane Polyamides","authors":"Saravanan Gowrisankar, Marius Lang, Peter R. Schreiner","doi":"10.1002/ejoc.202500643","DOIUrl":"https://doi.org/10.1002/ejoc.202500643","url":null,"abstract":"We report the synthesis and characterization of a new family of single‐component polyamides incorporating rigid diamantane monomers, and investigate their structural, thermal, and nonlinear optical properties. These polymers are largely amorphous and exhibit exceptional thermal stability, with decomposition events in the 400–600 °C range, significantly exceeding those of conventional nylons such as nylon‐6 and nylon‐66. Thermal analysis further shows that polyamides containing aromatic units retain higher residual yields than purely aliphatic analogues. Powder X‐Ray diffraction, dynamic light scattering, and scanning electron microscopy reveal pronounced morphological differences, ranging from irregular nanoscale particulates to smooth, rubbery domains. A direct correlation between morphology and optical behavior is observed: polyamides with disordered or finely particulate structures display intrinsic white‐light emission (WLE, 490–700 nm, λmax ≈ 610 nm) under continuous near‐infrared (980 nm) laser irradiation, whereas the smooth morphology suppresses this response. Importantly, this dopant‐free WLE is unprecedented for polyamides, identifying diamantane‐based polymers as an attractive platform for efficient, thermally robust, and cost‐effective organic light‐emitting materials.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"40 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145215860","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

A New Paradigm for the Supramolecular Structure of Laterally Offset Diarenes: Polymorphs II of Para‐Substituted Acetophenone Azines, YpPh(Me)CNNC(Me)PhYp (Y = Cl, Br, CH3) 横向偏置双芳烃超分子结构的新范式：对取代苯乙酮Azines的多晶型II， Yp - Ph - (Me)C <s:1> N - N <s:1> C(Me) - Ph - Yp （Y = Cl, Br, CH3）

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-04 DOI: 10.1002/ejoc.202500713

Harmeet Bhoday, Kaidi Yang, Steven P. Kelley, Rainer E. Glaser

{"title":"A New Paradigm for the Supramolecular Structure of Laterally Offset Diarenes: Polymorphs II of Para‐Substituted Acetophenone Azines, YpPh(Me)CNNC(Me)PhYp (Y = Cl, Br, CH3)","authors":"Harmeet Bhoday, Kaidi Yang, Steven P. Kelley, Rainer E. Glaser","doi":"10.1002/ejoc.202500713","DOIUrl":"https://doi.org/10.1002/ejoc.202500713","url":null,"abstract":"The crystal structures of polymorphs II of acetophenone azines YpPhRCNNCRPhYp with R = CH3 and Y = Cl (1M), Br (2M), and CH3 (8M) are discussed. The azine molecules in polymorphs II are Ci‐symmetric with trans‐azine moieties and conrotatory phenyl twists. Polymorphs 1M‐I and 2M‐I contain C2‐symmetric enantiomers with pronounced azine twists and disrotatory phenyl twists and allow for strong lateral double T‐contacts. The three polymorphs II exemplify the new Paradigm IV for the supramolecular architectures of “laterally offset diarenes” and result in “shiplap/flat” idioteloamphiphile monolayers. Intralayer lateral attraction is provided by edge‐to‐face arene‐arene contacts between molecules with substantial longitudinal offset and involves arene edges bridging one azine‐N and one phenyl center (EAzArB synthon) or one phenyl center and substituent Y (EYArB synthon) of different neighbors. These bridging synthons are characterized by a survey of pertinent structure parameters and their structural significance is corroborated by analysis of distance mapped Hirshfeld surfaces and the computation of 2D‐fingerprint plots. The edge‐to‐face contacts are the most attractive intermolecular interactions, and these interactions are quantified via the computed pair interaction energies and the results of aromatic analyzer analysis. Synthon binding energies and lattice energies are determined to assess polymorph preference energies.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"99 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145215542","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

Visible‐Light‐Promoted Cascade Acylmethylation/Annulation of N‐Alkene‐Linked Indoles with Sulfoxonium Ylides: Synthesis of Acylmethylated Pyrrolo[1,2‐a]indoles 可见光促进N -烯烃连接的吲哚与亚砜酰化的级联酰基甲基化/环化：酰基甲基化吡咯[1,2 - a]吲哚的合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-04 DOI: 10.1002/ejoc.202500619

Fan Wu, Yuzhen Xie, Hongni Qin, Yong Zhang, Song Sun

引用次数: 0

Discovery of Some New Heterocyclic Systems from Carbene‐Based Reactions of Indigo and N‐Methyl Derivatives 靛蓝和N -甲基衍生物在碳基反应中发现了一些新的杂环体系

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ejoc.202500525

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

{"title":"Discovery of Some New Heterocyclic Systems from Carbene‐Based Reactions of Indigo and N‐Methyl Derivatives","authors":"Sarfaraz Ali Ghumro, Matthew J. Perry, Christopher Richardson, Stephen G. Pyne, John B. Bremner, Paul A. Keller","doi":"10.1002/ejoc.202500525","DOIUrl":"https://doi.org/10.1002/ejoc.202500525","url":null,"abstract":"Reactions of N,N′‐dimethylindigo with dichlorocarbene or rhodium carbenoids have been investigated leading to the one‐pot production of new, complex heterocyclic derivatives. One of these arises from an overall ring interconversion process with ring expansion to afford a novel eight‐membered ring‐fused benz[6,7][1,5]oxazocino[3,2‐b]indol‐13‐one derivative. Alternatively, an overall ring construction process gives rise to an unprecedented spirocyclic 2H,4H‐spiro[furo[3,2‐b]indole‐3,2′‐indoline] system. A number of products with an embedded 6H‐pyrido[1,2‐a:3,4‐b′]diindole core from reaction with a rhodium malonyl ester carbenoid intermediate are also reported, plus some other carbenoid‐derived products. A solvent dependence is apparent with these reactions. Reaction path differences are also seen using N‐methylindigo or the parent indigo as the substrate and possible mechanisms are proposed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"73 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145203647","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

Nickel(II) Bromide Catalyzed Multicomponent Cyclization to Access 4‐Substituted 2‐Iminothiazolines 镍（II）溴化催化多组分环化制备4 -取代的2 -亚氨基噻唑类化合物

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-30 DOI: 10.1002/ejoc.202500830

Vu H. Luu, Khoa H. D. Nguyen, Kien Q. Truong, Han B. Tran, Hoang V. M. Trinh, Thuy T. Ca, Tung T. Nguyen

引用次数: 0