Asian Journal of Organic Chemistry最新文献

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Recent Advances on Synthesis of 2H‐Chromenes, and Chromenes Fused Hetrocyclic Compounds 2H-Chromenes 和 Chromenes Fused Hetrocyclic 化合物合成的最新进展

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400259

Chromenes and 2H‐Chromenes are vital components of natural products, pharmaceuticals, and agrochemicals that have captured the attention of researchers worldwide. These heterocyclic compounds represent an essential class of structural scaffolds, and the quest for their synthesis in a mild and straightforward way has gained significant momentum. Chromenes are oxygen‐containing heterocycles that have been widely studied due to their potential medicinal properties. In the last two decades, researchers have made remarkable progress towards the synthesis of chromene based heterocyclic compounds using O‐propargylated benzaldehydes as a substrate. These substrates are highly versatile and contain functional groups that make them ideal for a wide range of reactions. This review article provides an in‐depth analysis of the latest advances in alkynes’ functionalization, emphasizing the substrate scope, limitations, regioselectivity control, and applications of these reactions. The review also covers a range of critical methods and strategies, including multicomponent reactions, used for the general synthesis of numerous types of chromene derivatives.

苯并吡喃和 2H 苯并吡喃是天然产品、药物和农用化学品的重要组成部分，吸引着全球研究人员的目光。这些杂环化合物是一类重要的结构支架，以温和、直接的方式合成它们的研究已取得了显著的进展。色烯是一种含氧杂环化合物，因其潜在的药用特性而被广泛研究。在过去二十年中，研究人员以 O-丙炔基苯甲醛为底物合成色烯类杂环化合物的研究取得了显著进展。这些底物用途广泛，所含的官能团使其成为各种反应的理想选择。这篇综述文章深入分析了炔烃官能化的最新进展，强调了这些反应的底物范围、局限性、区域选择性控制和应用。综述还涵盖了一系列关键的方法和策略，包括多组分反应，这些方法和策略用于多种类型色烯衍生物的一般合成。

引用次数: 0

Pd(0)/TPPMS‐Catalyzed Tsuji–Trost Type Cross‐Coupling of Allylic Alcohols with Organoboron Compounds in Water Pd(0)/TPPMS 催化的水中烯丙基醇与有机硼化合物的辻-特罗斯特型交叉偶联反应

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400132

We demonstrated that the combination of a Pd(0) catalyst and a water‐soluble TPPMS ligand has high activity for the direct arylation of readily available allylic alcohols in the Tsuji–Trost type cross‐coupling. Various organoboron reagents can be applied, enabling rapid access to the corresponding arylated products with a wide range of functional group tolerance. Kinetic studies revealed a first‐order rate dependence for the allylic alcohol, boronic acid, CsF and Pd(0)/TPPMS concentrations. A Hammett study found a slightly positive ρ value of 0.79, suggesting that a partial negative charge is generated on the aromatic ring of the aryl boronate in the rate‐determining transmetalation step. Based on several control experiments, we concluded that the transmetalation employing CsF would proceed via the oxo‐palladium mechanism.

我们证明了钯(0)催化剂和水溶性 TPPMS 配体的组合在辻-特罗斯特型交叉偶联中直接芳基化易得的烯丙基醇方面具有很高的活性。可以使用各种有机硼试剂，从而快速获得具有广泛官能团耐受性的相应芳基化产物。动力学研究表明，烯丙基醇、硼酸、CsF 和 Pd(0)/TPPMS 的浓度具有一阶速率依赖性。Hammett 研究发现，r 值为 0.79，略微偏正，这表明在决定速率的转金属步骤中，芳基硼酸酯的芳香环上产生了部分负电荷。根据几次对照实验，我们得出结论，使用铯钯的反金属化反应将通过氧化钯机制进行。

引用次数: 0

Intramolecular [2+2] Cycloadditions of α‐Heteroatom Substituted γ,δ‐Unsaturated Ketenes α-杂原子取代的γ、δ-不饱和酮的分子内 [2+2] 环加成反应

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400302

An improved synthetic procedure for the intramolecular ketene [2+2] cycloaddition was developed for the preparation of 1‐heteroatom‐substituted bicyclo[2.1.1]hexan‐5‐ones. It was found that the use of the Mukaiyama reagent (2‐chloro‐N‐methyl‐pyridinium iodide) was key to efficiently generate the α‐heteroatom substituted homoallyl ketene intermediate for the cycloaddition reaction. The synthetic utility of the resulting bicyclic ketone was demonstrated through the preparation of a saturated variant of vortioxetine.

为制备 1-异原子取代的双环[2.1.1]己烷-5-酮，开发了一种改进的分子内酮[2+2]环化合成程序。研究发现，使用 Mukaiyama 试剂（2-氯-N-甲基吡啶鎓碘化物）是高效生成用于环化反应的 α-杂原子取代均烯丙基酮中间体的关键。通过制备伏替西汀的生物异构变体，证明了所得双环酮的合成用途。

引用次数: 0

Collective Synthesis of Furanocoumarin Natural Products Through a Radical‐mediated Construction of Furanocoumarin Skeletons 通过自由基介导的呋喃香豆素骨架构建集体合成呋喃香豆素天然产物

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400277

Furanocoumarins are attractive targets in the synthetic organic and medicinal chemistry field because of their structural diversity and interesting biological properties. Herein, we describe the synthesis of furanocoumarin natural products from common furanocoumarin skeletons. A key step was a novel intramolecular radical cyclization onto nitrile to synthesize angular and linear franocoumarins, which was optimized by reacting iodocoumarin derivatives in the presence of (Me₃Si)₃SiH and oxygen. These compounds served as intermediates in the syntheses of vaginidiol, vaginidin, oroselol, multivittan D, gaudichaudine, oreoselone, peucedanin, and smyrindiol, successfully demonstrating the versatility of the intermediates and utility of the radical cyclization method for accessing furanocoumarin natural products.

呋喃香豆素因其结构的多样性和有趣的生物特性而成为有机合成和药物化学领域极具吸引力的目标。在此，我们介绍了从常见呋喃香豆素骨架合成呋喃香豆素天然产物的过程。其中一个关键步骤是在 (Me3Si)3SiH 和氧的存在下，通过新型分子内自由基环化反应合成角型和线型呋喃香豆素。这些化合物在合成迷迭香二醇、迷迭香苷、oselol、multivittan D、gaudichaudine、oreoselone、peucedanin 和 smyrindiol 的过程中起到了中间体的作用，成功证明了中间体的多功能性和自由基环化方法在获得呋喃香豆素天然产物方面的实用性。

引用次数: 0

Synthesis and Properties of Fused Polycyclic Donor–Acceptor Compounds Containing Carbazole and Diazapyrene Skeletons 含咔唑和重氮apyrene 骨架的融合多环受体-捐体化合物的合成及其性质

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400289

Fused polycyclic aromatic compounds containing carbazole and diazapyrene skeletons as electron donors and acceptors, respectively, were synthesized in a few steps from readily accessible starting materials. The incorporation of diazapyrene units into the polycyclic compounds resulted in significant bathochromic shifts in their absorption and emission bands compared to those of the corresponding carbazole derivatives. Electrochemical measurements and density functional theory calculations were performed to gain further insight into their electronic properties. Our findings demonstrate that the incorporation of nitrogen atoms and substituents, as well as the different topologies of the fused‐ring system, exert a profound effect on the electronic properties of the polycyclic compounds.

利用容易获得的起始材料，通过几个步骤就合成了分别以咔唑和重氮apyrene 为电子供体和受体骨架的融合多环芳香族化合物。与相应的咔唑衍生物相比，在多环化合物中加入重氮apyrene 单元会使其吸收带和发射带发生明显的浴色偏移。为了进一步了解它们的电子特性，我们进行了电化学测量和密度泛函理论计算。我们的研究结果表明，氮原子和取代基的加入以及熔环体系的不同拓扑结构对多环化合物的电子特性产生了深远的影响。

引用次数: 0

pH Sensitive Dual Cross‐Linked Anionic and Amphoteric Interpenetrating Network Hydrogels for Adsorptive Removal of Anionic and Cationic Dyes 用于吸附去除阴离子和阳离子染料的 pH 值敏感型双交联阴离子和两性互穿网络水凝胶

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400238

The contamination of water by organic dye compounds are worldwide environmental problem due to their highly toxic nature. To address this environmental issue, a simple technique with highly efficient dye removal was developed to prepare pH‐ sensitive dual‐crosslinked anionic and amphoteric interpenetrating network (IPN) hydrogels based on Na‐carboxymethyl cellulose (Na‐CMC) using jute stick‐based cellulose. Crosslinked Na‐CMC and crosslinked κ‐carrageenan (KC) were interlaced by H‐bonding in anionic IPN hydrogel (An‐gel), but crosslinked Na‐CMC and crosslinked Chitosan (CS) were interlaced by electrostatic interaction in amphoteric IPN hydrogel (Am‐gel). In various operating conditions (pH, temperature, etc.) An‐gel displayed a higher number of swelling ratios of about 2560% at pH 7.2 and Am‐gel of about 1874% at pH 5.5. Based on the point of zero charge, An‐gel achieved the maximum removal efficiency of 81.62 % for methylene blue (MB) at pH 7.2, whereas Am‐gel achieved 85.38% removal efficiency for eosin yellow (EY) at pH 5.5. The adsorption kinetics of IPN hydrogels followed a pseudo‐second order model and best fitted by Langmuir isotherm model. The removal efficiency of MB and EY decreased slightly with increasing temperature. The values of ΔH°, ΔG°, and ΔS° indicated an exothermic, spontaneous, and disordered adsorption process.

有机染料因其剧毒性而成为世界性的环境问题。为了解决这一环境问题，我们开发了一种高效去除染料的简单技术，利用黄麻棒纤维素制备了基于 Na- 羧甲基纤维素（Na-CMC）的 pH 值敏感的双交联阴离子和两性互穿网络（IPN）水凝胶。在阴离子 IPN 水凝胶（An-gel）中，交联的 Na-CMC 和交联的 k-卡拉胶（KC）通过 H 键交错；而在两性 IPN 水凝胶（Am-gel）中，交联的 Na-CMC 和交联的壳聚糖（CS）通过静电作用交错。在不同的操作条件（pH 值、温度等）下，An-凝胶在 pH 值为 7.2 时的溶胀率约为 2560%，而 Am-凝胶在 pH 值为 5.5 时的溶胀率约为 1874%。根据零电荷点，An-凝胶在 pH 值为 7.2 时对亚甲蓝（MB）的去除率最高，达到 81.6%，而 Am-凝胶在 pH 值为 5.5 时对曙红（EY）的去除率最高，达到 85.3%。IPN 水凝胶的吸附动力学遵循伪二阶模型，与 Langmuir 等温线模型的拟合度最高。随着温度的升高，MB 和 EY 的去除率略有下降。ΔH°、ΔS°和ΔG°的值表明这是一个放热、自发和无序的吸附过程。

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引用次数: 0

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities 路易斯酸催化的丙炔醇与 2-烯丙基苯酚的串联嵌段反应及其抗肿瘤活性

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400265

A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range of structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols and 2‐allylphenols as substrates in the presence of Bi(OTf)₃ and AgOTf is described. This Lewis acid catalyzed [3+2] annulation protocol, which tolerates a great deal of functional groups, proceeds through a sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐exo‐trig cyclization, 5‐endo‐trig cyclization, and proton exchange sequences, affording a versatile approach for accessing oxygen‐containing tricyclic skeletons in moderate‐to‐excellent yields. In addition, most of the obtained compounds exhibited anti‐tumor activities against three types of human cancer cell lines in vitro, including Caco‐2 colon cancer cells, MCF‐7 breast cancer cells, and Hepg‐2 liver cancer cells.

本文介绍了一种新型的三氟甲磺酸铋（III）催化和无害环境的合成策略，该策略可在 Bi(OTf)3 和 AgOTf 的存在下，以易于处理的丙炔醇和 2-烯丙基苯酚为底物，构建结构多样、复杂的 [5,6,5]- 含氧三环框架。这种路易斯酸催化的[3 + 2]环化协议可容忍大量的官能团，通过依次进行的迈耶-舒斯特重排、亲核取代、5-外-三环化、5-内-三环化和质子交换序列，提供了一种以中等至优异收率获得含氧三环骨架的多功能方法。此外，所获得的大多数化合物在体外对三种人类癌细胞系（包括 Caco-2 结肠癌细胞、MCF-7 乳腺癌细胞和 Hepg-2 肝癌细胞）具有抗肿瘤活性。

引用次数: 0

Silica Sulphuric Acid Catalyzed Intra‐Molecular Alkyne Carbonyl Metathesis (ACM): A Rapid Access to 2H‐Chromenes 二氧化硅硫酸催化的分子内炔羰基复分解反应 (ACM)：快速获得 2H- Chromenes

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400219

A highly efficient, convenient and ecofriendly approach to access highly functionalized 2H‐chromenes via intramolecular aldehyde alkyne metathesis reaction was established starting from readily accessible alkyne‐tethered 2‐((3‐phenylprop‐2‐yn‐1‐yl) oxy)benzaldehydes and catalyzed by silica sulfuric acid (SiO₂‐OSO₃H, SSA) coupled with microwave irradiation. This reaction was well tolerated for various substituents including different functional groups and furnished the desired highly functionalized 2H‐chromene derivatives in good to excellent yields in a very short time. A systematic study of the conventional heating approach and microwave irradiation was performed to demonstrate the advantages of the microwave‐assisted condition in terms of high yield and shorter reaction time.

从容易获得的炔拴 2-((3-苯基丙-2-炔-1-基)氧基)苯甲醛开始，在二氧化硅硫酸（SiO2-OSO3H，SSA）和微波辐照的催化下，建立了一种通过分子内醛炔元合成反应获得高官能度 2H-铬烯的高效、便捷和生态友好的方法。这种反应对包括不同官能团在内的各种取代基都有很好的耐受性，并能在很短的时间内以良好到极好的收率获得所需的高官能度 2H-chromene 衍生物。对传统加热方法和微波辐照进行了系统研究，以证明微波辅助条件在高产率和缩短反应时间方面的优势。

引用次数: 0

Mechanism and Origins of Nucleophile‐Controlled Regioselectivity of Palladium‐Catalyzed Allylic C−H Amination of 1,4‐Dienes: A Computational Study 钯催化 1,4-二烯的烯丙基 C-H 氨基化的核亲和剂控制的区域选择性的机理和起源：计算研究

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400264

Density functional theory calculations have been conducted to investigate the palladium‐catalyzed allylic C−H amination of 1,4‐dienes with commonly available amines. The computations indicate that the reaction begins with the allylic C−H bond cleavage through the concerted proton and two‐electron transfer process to forge the η³‐allyl Pd(II) species. The ensuing C−N bond formation was found to be highly dependent on the basicity of the nucleophile, enabling the regioselectivity switch upon change of the nucleophile. With the weakly basic aromatic amine, the reaction occurs through the hydrogen‐bonding enabled inner‐sphere nucleophilic attack pathway. The distance between the reacting carbon atom and the terminal carbon atom is responsible for the Z/E‐selectivity. The regioselectivity is primarily due to steric repulsion between the allyl group and the ligand. On the other hand, the outer‐sphere nucleophilic attack pathway is favored for the reaction with the more basic aliphatic cyclic amine. The change of the coordinating mode of the allylic moiety was found to play a crucial role in determining the regioselectivity.

为了研究钯催化的 1,4 二烯与常见胺的烯丙基 C-H 氨化反应，我们进行了密度泛函理论计算。计算结果表明，反应开始时，烯丙基 C-H 键通过质子和双电子协同转移过程裂解，形成 h3-烯丙基 Pd(II) 物种。研究发现，随后形成的 C-N 键与亲核体的碱性有很大关系，因此在改变亲核体时可以实现区域选择性转换。对于弱碱性芳香胺，反应是通过氢键促成的内圈亲核攻击途径发生的。反应碳原子与末端碳原子之间的距离决定了 Z/E 选择性。区域选择性主要是由于烯丙基和配体之间的立体斥力。另一方面，在与碱性较强的脂肪族环胺反应时，外层亲核攻击途径更受青睐。研究发现，烯丙基配位方式的改变在决定区域选择性方面起着至关重要的作用。

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引用次数: 0

V–Catalyzed Direct Ortho‐Aminomethylation of Phenols V 催化苯酚的直接正氨甲基化反应

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400194

A strategy for cross‐dehydrogenative C(sp2)‐C(sp3) coupling was developed by direct and highly selective V‐catalyzed ortho‐aminomethylation of phenol with aniline derivatives. A series of aminomethylphenol compounds were obtained in moderate to good yields under mild reaction conditions and with a broad substrate scope. A possible radical mechanism was proposed, and it was found that the coordination of phenolic hydroxyl groups with V⁵⁺ was crucial for the effective activation of the ortho position.

通过苯酚与苯胺衍生物直接和高选择性的 V 催化邻氨基甲基化反应，开发了一种 C（sp2）-C（sp3）交叉脱氢偶联策略。在温和的反应条件下，获得了一系列氨甲基苯酚化合物，收率从中等到良好，底物范围广泛。研究人员提出了一种可能的自由基机理，并发现酚羟基与 V5+ 的配位是有效激活正位的关键。

引用次数: 0

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Asian Journal of Organic Chemistry

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