Asian Journal of Organic Chemistry最新文献

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Segmental Deuterium Labeling of Alkyl Chains by Nickel–Mediated Desulfurization 镍介导脱硫的烷基链段氘标记

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.202500520

Carl Recsei , Reilly E. Sonstrom , Tamim Darwish

A general means to access segmentally deuterium‐labeled alkyl chains for applications in mass spectrometry, neutron scattering, and related biochemical studies is reported, using a key nickel boride mediated reductive desulfurization of substituted thiophenes. This approach enabled the preparation of (3,3,4,4,5,5,6,6‐²H₈)undecanoic acid and 1‐amino(1,1,2,2,3,3,4,4‐²H₈)nonane, using only recrystallization or distillation for purification. Both compounds featured segments of four deuterated carbon atoms with > 98.5% overall deuterium incorporation. To assess site‐specific deuterium retention during desulfurization, we demonstrated the utility of molecular rotational resonance (MRR) spectroscopy, which revealed the degree, position, and magnitude of isotope scrambling in a key thiophene reductive desulfurization step and established the methods set forth herein as being suitable for the construction of mass spectrometric standards and applicable to the synthesis of any CH₃(CH₂)_a(CD₂)_b(CH₂)_cCOOH (3 ≤ a ≤ 13, 3 ≤ b ≤ 6, c ≥ 1) using only commercially‐available materials. Our studies revealed extensive exchange of the hydrogen atoms on the thiophene carbons during saturation of the ring, ruling out an idealized schema of the reaction that is present in the literature. We further observed reagent‐dependent levels of isotopic scrambling at the benzylic position during desulfurization, challenging the assumption of benzylic stereospecificity in nickel‐mediated reductive desulfurization while affirming the reaction's applicability for segmental deuterium labeling.

本文报道了一种获取分段氘标记烷基链的一般方法，用于质谱分析、中子散射和相关生化研究，使用关键的硼化镍介导的取代噻吩的还原脱硫。该方法可以制备（3,3,4,4,5,5,6,6 - 2H8）十一烷酸和1 -氨基（1,1,2,2,3,3,4,4 - 2H8）壬烷，仅使用重结晶或蒸馏进行纯化。这两种化合物都具有四个氘化碳原子的片段，总氘含量为98.5%。为了评估脱硫过程中特定位点的氘保留，我们展示了分子旋转共振（MRR）光谱的实用性，它揭示了硫代噻吩还原脱硫关键步骤中同位素置乱的程度、位置和大小，并建立了适用于构建质谱标准的方法，适用于合成任何CH3(CH2)a(CD2)b(CH2)cCOOH(3≤a≤13,3≤b≤6，C≥1)仅使用市售材料。我们的研究表明，在环饱和期间，噻吩碳上的氢原子进行了广泛的交换，排除了文献中存在的理想反应模式。我们进一步观察到，在脱硫过程中，试剂依赖的同位素水平在苯基位置上混乱，挑战了镍介导的还原脱硫中苯基立体特异性的假设，同时肯定了该反应对段氘标记的适用性。

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引用次数: 0

Applications of N─F─Based Reagents in the Synthesis of Organochalcogen Compounds N─F─基试剂在有机醇类化合物合成中的应用

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.202500605

Thiago Anjos , Mateus W. Rambo , Prof. Damiano Tanini , Prof. Dr. Alan Diego C. Santos , Prof. Ricardo F. Schumacher , Prof. Filipe Penteado

Herein, we present a comprehensive review of recent synthetic strategies for the construction of chalcogen‐decorated compounds (since 2016), focusing on the generation of chalcogen‐based electrophilic or radical species through the use of N─F reagents as oxidants. Several chalcogen compounds have been employed as sources, including chalcogenides, diorganyl dichalcogenides, chalcogenols, chalcogenocyanides, and silver trifluoromethanethiolate. Remarkable advances in the preparation of heterocycles, carbocycles, and acyclic molecules containing chalcogens have been thoroughly discussed. Additionally, this review aims to emphasize mechanistic insights from selected studies and to highlight the potential application of these strategies in building molecular complexity. Finally, we hope to inspire future readers to explore new reactivities and possibilities for the development of novel synthetic strategies under mild and sustainable conditions.

在此，我们全面回顾了近年来构建含硫修饰化合物的合成策略（自2016年以来），重点介绍了利用N─F试剂作为氧化剂生成含硫基亲电或自由基的方法。几种含硫化合物已被用作来源，包括硫族化合物、二有机二硫族化合物、硫族醇、硫族氰化物和三氟甲硫酸银。详细讨论了含硫化合物的杂环、碳环和无环分子的制备方面取得的显著进展。此外，本综述旨在强调从选定的研究中获得的机制见解，并强调这些策略在构建分子复杂性方面的潜在应用。最后，我们希望启发未来的读者在温和和可持续的条件下探索新的反应和发展新的合成策略的可能性。

引用次数: 0

One‐Pot Functionalization at C‐2,2′‐Oxidation and C‐3,3′‐Bromination of 3,3′‐Bis‐7‐Azaindolylmethane Using NBS/CAN as a Reagent: Synthesis of Brominated 3,3′‐Bis‐7‐Aza‐2‐indalones 以NBS/CAN为试剂对3,3 ' - Bis - 7 -氮杂吲哚甲烷进行C‐2,2 ' -氧化和C‐3,3 ' -溴化的一锅功能化：合成溴化3,3 ' - Bis - 7 - Aza - 2 -吲哚酮

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70247

Pavithra Elavarasan , Sathananthan Kannadasan , Ponnusamy Shanmugam

The first study of the NBS/ceric (IV) ammonium nitrate (CAN) has emerged as a powerful and efficient reagent for the difunctionalization at C‐2,2′‐oxidation and C‐3,3′‐bromination of 3,3′‐bis‐7‐azaindolyl methane to form isolable diastereomers of polybrominated 7‐aza‐bis‐2‐indalones as established by ¹H NMR study. The scope of the reaction, characterization of products including XRD technique, and a plausible mechanism for the formation of products are described. Synthetic use of one of the products thus obtained, namely 3′‐methylene bis (3,5‐dibromo‐1‐methyl‐1,3‐dihydro‐2H‐pyrrolo[2,3‐b]pyridin‐2‐one), has been demonstrated by the synthesis of a functionally diverse dispiro[pyrrolo[2,3‐b]pyridine‐3,1′‐cycloheptane derivative by a sequence of reactions (1) zinc/AcOH reduction, (2) allylation, and (3) RCM reaction using Grubbs‐II catalyst.

NBS/ceric （IV）硝酸铵（CAN）作为一种强大而有效的试剂，在C‐2,2′-氧化和C‐3,3′-溴化的3,3′-双氮杂酰基甲烷中形成可分离的多溴化7‐aza‐双氮杂酰基吲哚酮的非对映体，这是通过1H NMR研究建立的。叙述了反应的范围、产物的表征（包括XRD技术）和产物形成的合理机理。通过一系列反应(1)锌/AcOH还原，(2)烯丙基化，(3)grbbs - II催化剂的RCM反应，合成了功能多样化的吡咯[2,3‐b]吡啶- 3,1 ' -环正烷衍生物，证明了3′‐亚甲基双(3,5‐二溴‐1‐甲基‐1,3‐二氢‐2H吡咯[2,3‐b]吡啶- 3,1′‐环正烷衍生物。

引用次数: 0

Synthesis, X‐ray, Hirshfeld Surface Analysis, Antibacterial Activity, and Computational Investigations of New Benzimidazo[1,2‐c]quinazolines and Indolo[2,3‐b]quinoxalines 新苯并咪唑[1,2 - c]和吲哚[2,3 - b]喹诺啉的合成、X射线、Hirshfeld表面分析、抗菌活性和计算研究

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70222

Houda Lamssane , Omar Abdellaoui , El Hassane Anouar , Amal Haoudi , Ahmed A. Elhenawy , Mohmed Mahmoud , Ahmed Mazzah , Youssef Kandri Rodi , Joel T. Mague , Hicham Elmsellem , El Mokhtar Essassi , Nada Kheira Sebbar

Novel benzimidazo[1,2‐c]quinazoline and indolo[2,3‐b]quinoxaline derivatives were synthesized and characterized using ¹H and ¹³C NMR, LC‐MS, and single‐crystal X‐ray diffraction techniques. A detailed analysis of the surface properties, intermolecular interactions, crystal packing characteristics, and antibacterial activity is given. The observed results reveal subtle differences in the Hirshfeld surface characteristics of these compounds, indicating variations in crystal packing and molecular recognition properties. The evaluation of antibacterial activity demonstrated that the synthesized compounds have promising broad‐spectrum efficacy against both Gram‐positive and Gram‐negative bacteria. Molecular docking analysis reveals strong binding interactions, emphasizing the potency of benzimidazo[1,2‐c]quinazoline and indolo[2,3‐b]quinoxaline derivatives to act as an antimicrobial agent. Moreover, quinazoline derivatives' superior absorption and permeability properties suggest enhanced oral bioavailability compared to ampicillin despite considerations of increased lipophilicity and potential drug interactions. These compounds' balanced physicochemical properties and favorable drug‐likeness scores indicate their potential as promising drug candidates, particularly for conditions requiring improved tissue penetration. Molecular dynamics simulations support the structural features, highlighting stable binding site occupation and strong off‐diagonal interactions, further underscoring its potential in drug design and development.

合成了新型苯并咪唑[1,2 - c]喹唑啉和吲哚[2,3 - b]喹唑啉衍生物，并利用1H和13C NMR、LC - MS和单晶X射线衍射技术对其进行了表征。详细分析了其表面特性、分子间相互作用、晶体填充特性和抗菌活性。观察到的结果揭示了这些化合物的赫希菲尔德表面特征的细微差异，表明晶体堆积和分子识别特性的变化。抗菌活性评价表明，合成的化合物对革兰氏阳性菌和革兰氏阴性菌均具有广谱抗菌作用。分子对接分析显示了强的结合相互作用，强调了苯并咪唑[1,2‐c]喹唑啉和吲哚[2,3‐b]喹诺啉衍生物作为抗菌药物的效力。此外，尽管考虑到亲脂性和潜在的药物相互作用，喹唑啉衍生物优越的吸收和渗透性表明，与氨苄西林相比，口服生物利用度更高。这些化合物平衡的物理化学性质和良好的药物相似性评分表明它们有潜力成为有希望的候选药物，特别是对于需要改善组织渗透的条件。分子动力学模拟支持其结构特征，突出了稳定的结合位点占用和强的非对角线相互作用，进一步强调了其在药物设计和开发中的潜力。

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引用次数: 0

Cu‐Doped UiO‐66‐NH2 Photocatalytic Cross‐Coupling of Arylamine C(sp2)‐H with Phenothiazine N─H Bonds Cu掺杂UiO - 66 - NH2光催化芳胺C(sp2) - H与吩噻嗪N─H键的交叉偶联

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70227

Yujuan Wu , Hongyang Xu , Qiulin Zhu , Yongfei Wang , Cuiping Wang , Zhizhi Hu , Zhiqiang Zhang

Herein, the Cu‐UiO‐66‐NH₂ photocatalyst was successfully constructed by precisely anchoring Cu active centers to Zr₆O₄(OH)₄ secondary building units (SBUs) in UiO‐66‐NH₂. Under mild reaction conditions, efficient C(sp²)─H/N─H cross‐coupling of phenothiazine with electron‐rich aniline was achieved without noble metal cocatalysts or organic photosensitizers. Experimental characterization results show that Cu doping can effectively suppress photogenerated carrier recombination. This not only broadens the visible light absorption range of UiO‐66‐NH₂, but also improves charge separation efficiency, thus significantly enhancing photocatalytic performance. In addition, hot filtration tests, gram‐scale reactions and multiple cycle experiments confirmed that the catalyst has excellent scalability and stability.

本文通过将Cu活性中心精确锚定在UiO‐66‐NH2中的Zr6O4(OH)4二级构建单元（SBUs）上，成功构建了Cu‐UiO‐66‐NH2光催化剂。在温和的反应条件下，在没有贵金属助催化剂和有机光敏剂的情况下，实现了吩噻嗪与富电子苯胺的高效C（sp2）─H/N─H交偶联反应。实验表征结果表明，Cu掺杂能有效抑制光生载流子复合。这不仅拓宽了UiO‐66‐NH2的可见光吸收范围，而且提高了电荷分离效率，从而显著提高了光催化性能。此外，热过滤试验、克级反应和多次循环实验证实了催化剂具有良好的可扩展性和稳定性。

引用次数: 0

Allylation and Alkynylation of α‐Trifluoromethyl Alkyl Iodide Enabled by Photoredox Induced Halogen‐Atom‐Transfer 光氧化还原诱导卤素-原子-转移的α -三氟甲基烷基碘烯丙基化和烷基化研究

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70230

Dabo Guo , Heyun Sheng , Mengjie Sun , Xiaobing Liu , Wenguang Li , Yongqi Yu , Huanping Xie , Weiguang Kong , Xue Li , Ting Li

Herein, we report a visible‐light‐catalyzed protocol for the trifluoroalkylation of alkynyl sulfones/ allyl sulfones using readily available α‐trifluoromethyl haloalkanes. This reaction is driven by DIPEA as a halogen‐atom transfer (XAT) reagent, providing a new strategy to access valuable propargyl and homoallyl trifluoromethyl compounds via Csp─Csp³ or Csp³─Csp³ bond formation. Notably, the methodology effectively suppresses the undesired β‐fluoride elimination of α‐trifluoromethyl radicals, thus avoiding the formation of gem‐difluoroalkenes. The transformation proceeds efficiently under mild conditions, affording the trifluoromethylated products in modest to excellent yields.

在此，我们报告了一种可见光催化的方案，使用现成的α -三氟甲基卤代烷进行炔基砜/烯基砜的三氟烷基化。该反应由DIPEA作为卤素原子转移（XAT）试剂驱动，提供了一种通过Csp─Csp3或Csp3─Csp3键形成有价值的丙炔和全烯丙基三氟甲基化合物的新策略。值得注意的是，该方法有效地抑制了α -三氟甲基自由基的β -氟消除，从而避免了gem -二氟烯烃的形成。在温和的条件下，转化有效地进行，提供中等至优异产量的三氟甲基化产品。

引用次数: 0

Role of Functional Groups on N‐Phenyl Pyrazolines in Antibacterial Activity: Combined Experimental and Computational Study N -苯基吡唑啉上官能团在抗菌活性中的作用：实验与计算相结合的研究

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70246

Yoga Priastomo , Anggit Fitria , Tutik Dwi Wahyuningsih , Deni Pranowo , Artania Adnin Tri Suma , Ninik Andriyani , Syaiful Muhklis

A crucial aspect of the antibacterial activity of N‐phenyl pyrazolines is the presence of specific substituents in their structures. Besides, several important elements require further investigation. In this study, we synthesized a series of N‐phenyl pyrazoline derivatives bearing electron‐donating group substituents derived from vanillin and electron‐withdrawing groups obtained from halogens. These compounds were evaluated against both Gram‐positive and Gram‐negative bacteria using in vitro and computational studies. The in vitro study revealed that N‐phenyl pyrazoline containing the electron‐donating groups (hydroxy [–OH] and methoxy [–OCH₃]) exhibited strong antibacterial activity against Gram‐negative bacteria, including Escherichia coli and Shigella flexneri, as well as moderate activity against Gram‐positive bacteria, such as Staphylococcus aureus and Bacillus subtilis. Furthermore, the results of the computational study supported these findings. It demonstrated that the electron‐donating groups (–OH and –OCH₃) were capable of forming molecular interactions similar to those of tetracycline with several key amino acids in the DNA gyrase (GyrB receptor), including Glu50, Asp73, and Arg76, which are essential for bacterial survival. However, the presence of the electron‐withdrawing groups (bromo [–Br] and chloro [–Cl]), in conjunction with the electron‐donating groups, decreased antibacterial activity against all tested bacteria, resulting in moderate to weak activity.

N -苯基吡唑啉抗菌活性的一个关键方面是其结构中特定取代基的存在。此外，有几个重要因素需要进一步调查。在这项研究中，我们合成了一系列N -苯基吡唑啉衍生物，这些衍生物含有来自香兰素的供电子基取代基和来自卤素的吸电子基。这些化合物通过体外和计算研究对革兰氏阳性和革兰氏阴性细菌进行了评估。体外研究表明，含有供电子基团（羟基[-OH]和甲氧基[-OCH3]）的N -苯基吡唑啉对革兰氏阴性菌（包括大肠杆菌和福氏志贺氏菌）具有较强的抗菌活性，对革兰氏阳性菌（如金黄色葡萄球菌和枯草芽孢杆菌）具有中等的抗菌活性。此外，计算研究的结果支持这些发现。结果表明，供电子基团（-OH和-OCH3）能够与DNA旋切酶（GyrB受体）中的几个关键氨基酸（包括Glu50、Asp73和Arg76）形成类似四环素的分子相互作用，这是细菌生存所必需的。然而，吸电子基团（溴[-Br]和氯[-Cl]）与供电子基团一起存在，降低了对所有测试细菌的抗菌活性，导致活性中等至弱。

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引用次数: 0

Recent Advances in Transformation of 1,4‐Diyn‐3‐ones and 1,4‐Diyn‐3‐ols 1,4 -二炔- 3 -酮和1,4 -二炔- 3 -醇转化研究进展

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.202500627

Qian Wang , Tao Wang

1,4‐Diyn‐3‐ones and 1,4‐diyn‐3‐ols have garnered considerable attention due to their distinctive characteristics, including multiple reaction sites. Numerous new reactions involving these compounds have been discovered in the past decades. Their transformations can provide a variety of useful O‐containing and N‐containing heterocycles with high regio‐ and stereoselectivity, including pyrones, pyrrolones, furans, and pyridones. In this review, we summarize the latest trends and developments of reactions involving 1,4‐diyn‐3‐ones and 1,4‐diyn‐3‐ols with a series of reagents including amines, water, N‐oxides, 1,3‐dicarbonyl compounds, quinolines, isoxazoles, and so on. We highlight the product diversity, selectivity, and applicability of these transformations and, where possible, discuss the underlying mechanistic rationale.

1,4 -二炔- 3 -酮和1,4 -二炔- 3 -醇由于其独特的特性（包括多个反应位点）而引起了相当大的关注。在过去的几十年里，已经发现了许多涉及这些化合物的新反应。它们的转化可以提供各种有用的含氧和含氮杂环，具有高区域选择性和立体选择性，包括吡咯酮、吡咯酮、呋喃和吡啶酮。本文综述了1,4 -二炔- 3酮和1,4 -二炔- 3醇与胺、水、N -氧化物、1,3 -二羰基化合物、喹啉类、异恶唑等试剂反应的最新进展。我们强调了这些转换的产品多样性、选择性和适用性，并在可能的情况下讨论了潜在的机制原理。

引用次数: 0

Synthesis of Succinimide‐Fused γ‐Carbolines via Rh(III)‐Catalyzed Annulation of Indolyl Azines With Maleimides Rh（III）催化吲哚嘧啶与马来酰亚胺环化合成琥珀酰亚胺融合γ -羰基胺

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70252

Anand Kumar , Seungeun Lee , Hoyoung Lee , Chae Yeon Park , Amitava Rakshit , Pargat Singh , In Su Kim

The rhodium(III)‐catalyzed oxidative annulation between indolyl azines and maleimides is presented, in which indolyl azines serve as both twofold ketimine precursors and internal oxidants. This process yields a range of succinimide‐fused γ‐carbolines. A series of post‐transformations for the synthesized products is also described.

介绍了铑（III）催化吲哚酰嗪和马来酰亚胺之间的氧化环反应，其中吲哚酰嗪既作为双氯胺酮前体又作为内氧化剂。这个过程产生一系列琥珀酰亚胺-融合γ -碳胺。对合成产物的一系列后转化也进行了描述。

引用次数: 0

Access to Functionalized Pyridoindolones Enabled by Rh(III)‐Catalyzed C─H Alkenylation/Cyclization of Indoles with Alkynes Rh（III）‐催化吲哚与炔的C─H烯基化/环化制备功能化吡啶吲哚

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-12-01 DOI: 10.1002/ajoc.70220

Jiaping Wu , Yehe Wu , Yuhao Wang , Minzhan Du , Meihua Xie , Jitan Zhang

Herein, we report a traceless directing group assisted Rh(III)‐catalyzed C─H cyclization cascade of indoles and (arylprop‐2‐yn‐1‐yl)malonates under redox‐free reaction conditions, thus providing a concise access to structurally diverse functionalized pyridoindolones. This transformation proceed smoothly with a tolerance of various functional groups and moderate to good efficiencies. In addition, the practical and stereoselective construction of 2‐alkenylated NH‐indole scaffold could be accomplished within 30 min by utilizing simple aromatic alkynes. Furthermore, the synthetic value of this strategy was demonstrated by the readily accessible and divergent transformations of products. A preliminary mechanism was also proposed based on a series of deuterating and control experiments.

在此，我们报道了在无氧化还原反应条件下，Rh（III）‐催化吲哚和（芳基prop‐2‐yn‐1‐yl）丙二酸酯的C─H环化级联反应，从而提供了一种结构多样的功能化吡啶多酮的简洁途径。这种转换可以在容忍各种官能团的情况下顺利进行，并且效率适中。此外，利用简单的芳香烃在30分钟内即可完成2 -烯基化NH -吲哚支架的实际立体选择性构建。此外，该策略的综合价值通过产品的易接近性和发散性转化来证明。通过一系列氘化和控制实验，初步提出了其机理。

引用次数: 0

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