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Solvent-free Simplistic Synthesis of Bis(indolyl) Methanes Using Tulsion®-8052 MP Resin 使用 Tulsion®-8052 MP 树脂无溶剂简单合成双(吲哚基)甲烷
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-08-07 DOI: 10.2174/0115701786318532240722113525
Suhas Sadaphal, Sanjay Gaikwad, Shubham Dagale, Suryakant Sapkal, Pratibha Randhavane, Jaishree Gawai
: Tulsion®-8052 MP cation resin catalyst accelerates chemical reaction by creating a suitable environment for the aldehyde and indole reactants to interact and form desired product bis(indolyl) methanes in solvent-free room temperature conditions. The uniqueness of this catalytic method is that it is eco-friendly, recyclable, selective, and operates on a variety of functional groups with good to excellent yield at room temperature conditions without the use of any hazardous solvents, high temperature, and inert atmosphere.
:Tulsion®-8052 MP 阳离子树脂催化剂可在无溶剂室温条件下为醛和吲哚反应物的相互作用创造适宜的环境,从而加速化学反应,并生成所需的双(吲哚基)甲烷。这种催化方法的独特之处在于它环保、可回收、选择性强,可在室温条件下对多种官能团进行催化反应,且无需使用任何有害溶剂、高温和惰性气氛,即可获得良好甚至优异的产率。
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引用次数: 0
Microwave-assisted Synthesis and Reactivity of Some Novel Chromenopyridine Derivatives Bearing 2,4-Diamino-3-Carbonitrile Moieties 含有 2,4-二氨基-3-腈分子的一些新型色并吡啶衍生物的微波辅助合成及其反应活性
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-08-07 DOI: 10.2174/0115701786316461240801065332
Amira Trabelsi, Emna khdhiri, Souhir Abid, Lujain M. Althobaiti, Houcine Ammar
: In the current study, we reported a cost-effective, simple strategy for the synthesis and reactivity of a novel series of chromenopyridine derivatives involving 2,4-diamino-3-carbonitrile moieties. These new compounds were synthesized in good yields from malononitrile and various chromene derivatives as a precursor, which was prepared by the reduction of iminocoumarin derivatives. The formed iminocoumarin was obtained by Knoevenagel condensation from malononitrile and different aromatic aldehydes. These novel chromenopyridine derivatives were further reacted with triethyl orthoformate under microwave irradiation to afford the final compounds, namely "chromenopyridine formimidate." The structures of all molecules were characterized by FT-IR, 1H NMR, 13C NMR, and elemental analysis.
:在当前的研究中,我们报告了一种具有成本效益的简单策略,用于合成和反应涉及 2,4-二氨基-3-甲腈分子的一系列新型色烯吡啶衍生物。这些新化合物是以丙二腈和各种色烯衍生物为前体,通过还原亚氨基香豆素衍生物合成的,收率很高。形成的亚氨基香豆素是由丙二腈和不同的芳香醛通过克诺文纳格尔缩合反应得到的。在微波辐照下,这些新型铬吡啶衍生物与原甲酸三乙酯进一步反应,得到最终化合物,即 "铬吡啶甲亚胺酯"。所有分子的结构都通过傅立叶变换红外光谱、1H NMR、13C NMR 和元素分析进行了表征。
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引用次数: 0
Synthesis, Spectral Characterization, Molecular Docking Studies, and Biological Evaluation of Pyranoquinolinyl Acrylic Acid (PQAA) Diastereomers as Antibacterial Agents Promoted by Indium (III) Triflate in 1-Butyl-3-Methylimidazolium Tetrafluoroborate Ionic Liquid 1-丁基-3-甲基咪唑鎓四氟硼酸盐离子液体中的三氟化铟 (III) 促进吡喃喹啉基丙烯酸 (PQAA) 非对映异构体的合成、光谱表征、分子对接研究和生物学评价
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-07-29 DOI: 10.2174/0115701786333234240725110033
K. venkatapathy, C. J. Magesh
In the present investigation, we report the multistep synthesis of pyranoquinolinyl acrylic acid (PQAA)/furoquinolinyl acrylic acid (FQAA) diastereomers via perkin condensation and reduction, followed by one-pot inverse electron demand Diels-Alder reaction among 2,3 dihydropyran, amine, and aromatic aldehyde mediated by indium (III) triflate in 1-butyl-3-methylimidazolium tetrafluoroborate (In(OTf)3/ [bmim]BF4) at 25.0-27.0oC. The pyranoquinolinyl acrylic acid/furoquinolinyl acrylic acid diastereomers were evaluated for their in vitro antibacterial activity. Molecular docking studies were carried out employing iGEMDOCK software to evaluate the mode of binding between UDP-N-acetylenolpyruvoyl glucosamine reductase and PQAA adducts. All the pyranoquinolinyl/ furoquinolinyl/tetrahydro-cyclopentaquinolinyl acrylic acid (PQAA/FQAA/CPQAA) diastereomers were thoroughly characterized by NMR, FT-IR, mass spectral, and CHN analysis.
在本研究中,我们报告了通过普金缩合和还原多步合成吡喃喹啉丙烯酸(PQAA)/呋喃喹啉丙烯酸(FQAA)非对映体的过程、然后在 1-丁基-3-甲基咪唑鎓四氟硼酸盐(In(OTf)3/ [bmim]BF4)中以三酸铟(III)为介质,在 25.0-27.0oC。对吡喃喹啉丙烯酸/呋喃喹啉丙烯酸非对映异构体的体外抗菌活性进行了评估。利用 iGEMDOCK 软件进行了分子对接研究,以评估 UDP-N-acetylenolpyruvoyl 葡萄糖胺还原酶与 PQAA 加合物之间的结合模式。所有吡喃喹啉基/呋喃喹啉基/四氢环戊喹啉基丙烯酸(PQAA/FQAA/CPQAA)非对映体都通过核磁共振、傅立叶变换红外光谱、质谱和碳氢化合物分析进行了全面表征。
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引用次数: 0
Semisynthesis and DFT Study of New Michael Adducts using (E)-Α-Atlantone, Isolated from Cedrus Atlantica Essential Oil 使用从亚特兰蒂斯雪松精油中分离出来的 (E)-Α-Atlantone 进行新型迈克尔加合物的半合成和 DFT 研究
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-07-18 DOI: 10.2174/0115701786321643240709114001
Rida Nejjari, Maryam Bashir, Houria Raji, Bouchra Es-Sounni, Mohamed Adardour, Farhan Siddique, Mohamed Bakhouch, Abdelkrim Mouzdahir, Ahmed Benharref, Noureddine Mazoir, Samir Chtita
: This work is devoted to the synthesis of divers Michael adducts from (E)-α-atlantone as an α,β-unsaturated ketone isolated from Cedrus atlantica essential oil. The (E)-α-atlantone is subjected to ethyl cyanoacetate, phenylmagnesium bromide, and ethanol to produce the corresponding 1,4-Michael adducts in good yields. The conjugate addition of the appropriate reagents onto (E)-α-atlantone proceeds in a regiospecific manner, closely governed by the nucleophilicity of the reagents as well as their stereospecific blocking. The structure of the obtained Michael adducts is established using NMR (1H & 13C) spectroscopy and elemental analysis. Likewise, the DFT method was utilized to comprehend the molecular properties, stability, and reactivity of the investigated compounds, as well as to explain the proposed mechanism. The computed outcomes are in good agreement with the experimental data.
:这项研究致力于从(E)-α-atlantone 中合成多种迈克尔加合物,(E)-α-atlantone 是一种从杉木精油中分离出来的 α、β-不饱和酮。将(E)-α-atlantone 与氰乙酸乙酯、苯基溴化镁和乙醇反应,可生成相应的 1,4-迈克尔加合物,收率很高。适当的试剂与(E)-α-阿特兰酮的共轭加成以区域特异性的方式进行,这与试剂的亲核性及其立体特异性阻断密切相关。利用核磁共振(1H & 13C)光谱和元素分析确定了所获得的迈克尔加合物的结构。同样,还利用 DFT 方法理解了所研究化合物的分子特性、稳定性和反应性,并解释了所提出的机理。计算结果与实验数据十分吻合。
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引用次数: 0
N-Alkylation of Amines Utilizing Magnetic Nano Chitosan Functionalized with EDTA/Co(II) 利用 EDTA/Co(II)官能化的磁性纳米壳聚糖进行胺的 N-烷基化反应
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-07-10 DOI: 10.2174/0115701786308650240705072830
Farzaneh Ebrahimzadeh
This research work has explored the application of a magnetic catalyst composed of coreshell nanoparticles [Fe3O4@SiO2@CS@EDTA/Co(II)], known as NCM@EDTA/Co(II), in the conversion of various alcohols containing electron-donating or electron-withdrawing groups into their respective secondary or primary amine derivatives. The investigation has focused on optimizing reaction conditions by considering factors, such as the inclusion of a base, duration of reaction time, reaction temperature, catalyst quantity, and choice of transition metal, in order to determine the optimal parameters. The most favorable outcomes have been achieved by using 0.2 mmol of catalyst per 1 mmol of substrate under reflux conditions for a duration ranging from 3 to 24 hours. The reaction has demonstrated high efficiency, with the catalyst's easy separation via an external magnetic field, stability, and recyclability, highlighting its potential applications in chemistry and industrial environments.
本研究工作探索了一种由核壳纳米粒子 [Fe3O4@SiO2@CS@EDTA/Co(II)] 组成的磁性催化剂(称为 NCM@EDTA/Co(II))在将各种含有电子奉献基团或电子吸收基团的醇类转化为各自的仲胺或伯胺衍生物中的应用。研究重点是优化反应条件,考虑的因素包括加入碱、反应时间长短、反应温度、催化剂数量和过渡金属的选择,以确定最佳参数。在回流条件下,每 1 毫摩尔底物使用 0.2 毫摩尔催化剂,反应时间从 3 小时到 24 小时不等,取得了最理想的结果。该反应表现出高效率,催化剂易于通过外部磁场分离,具有稳定性和可回收性,突出了其在化学和工业环境中的应用潜力。
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引用次数: 0
Synthesis of 4-hydroxyquinoline-2(1H)-ones Based on Ag(I)-catalyzed Carbon Dioxide Fixation on 2-alknylanilines 基于 Ag(I)-catalyzed Carbon Dioxide Fixation on 2-alknylanilines 的 4-羟基喹啉-2(1H)-酮的合成
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-06-24 DOI: 10.2174/0115701786302455240603070018
Xin-Yu Lin, Guo-Jun Chen, Su-Zhe Wu, Ke-Xuan Xu, Xiao-Tian Zhang, Qi Feng
: 4-Hydroxyquinoline-2(1H)-ones exhibit multiple biological activities, and studying their synthetic methods is of great significance. In the presence of tetramethylguanidine and silver nitrate, 4-hydroxyquinoline-2(1H)-ones were efficiently synthesized from 2-ethynylanilines and carbon dioxide under atmospheric pressure. The reaction conditions, such as types of silver catalysts and reaction solvents, were optimized, and the applicability of the substrate was preliminarily investigated. This method provides an alternative pathway for the synthesis of 4-hydroxyquinoline-2(1H)-ones and the conversion and utilization of carbon dioxide.
:4-羟基喹啉-2(1H)-酮具有多种生物活性,研究其合成方法具有重要意义。在四甲基胍和硝酸银存在下,4-羟基喹啉-2(1H)-酮在常压下由 2-乙炔基苯胺和二氧化碳高效合成。对银催化剂和反应溶剂等反应条件进行了优化,并初步研究了底物的适用性。该方法为 4-羟基喹啉-2(1H)-酮的合成以及二氧化碳的转化和利用提供了另一条途径。
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引用次数: 0
Utilizing NCP@PO(OH)2 as a Core-Shell Magnetic Nano-Catalyst for the Conversion of β-Hydroxy Nitrile to α,β-Unsaturated Carboxylic Acid 利用 NCP@PO(OH)2 作为核壳磁性纳米催化剂将 β-羟基腈转化为 α,β-不饱和羧酸
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-05-30 DOI: 10.2174/0115701786307956240522081438
Farzaneh Ebrahimzadeh
: The synthesis of α,β-unsaturated compounds is crucial in organic chemistry, especially in drug discovery and pharmaceutical development. In this study, NCP@POCl2-x (Fe3O4@SiO2@chitosan@POCl2-x) has been introduced as a new, environmentally friendly, and highly efficient heterogeneous magnetic nanocatalyst for the synthesis of α,β-unsaturated carboxylic acids. This catalyst facilitates the in situ transformation of POCl2-x to PO(OH)2 in the presence of water, effectively converting β-hydroxy nitriles into α,β-unsaturated carboxylic acids through a specific mechanism involving water and heat. The reactions display notable regioselectivity, leading to high-purity products and quantitative yields. NCP@PO(OH)2 exhibits heterogeneity, magnetic properties, straightforward recovery, and outstanding performance, making it a valuable catalyst for efficient and selective transformations of β-hydroxy nitriles. Additionally, it can be easily separated from the mixture of reactions using external magnetic forces.
:α、β-不饱和化合物的合成在有机化学,尤其是药物发现和医药开发中至关重要。在本研究中,NCP@POCl2-x(Fe3O4@SiO2@壳聚糖@POCl2-x)作为一种新型、环保、高效的异相磁性纳米催化剂被引入到 α,β-不饱和羧酸的合成中。这种催化剂可促进 POCl2-x 在有水的情况下原位转化为 PO(OH)2,通过涉及水和热的特定机理,有效地将β-羟基腈转化为α,β-不饱和羧酸。这些反应具有显著的区域选择性,可得到高纯度产品和定量收率。NCP@PO(OH)2 具有异质性、磁性、可直接回收和出色的性能,使其成为高效、选择性地转化 β-羟基腈的重要催化剂。此外,它还能利用外磁力轻松地从反应混合物中分离出来。
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引用次数: 0
Ultrasound-assisted Synthesis of β-(N-arylamino)Acrylates Derivatives, Key Intermediates of Biopotent Compounds 超声辅助合成生物活性化合物的关键中间体 β-(N-芳基氨基)丙烯酸酯衍生物
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-05-29 DOI: 10.2174/0115701786305078240521085708
Gabriel de Oliveira Costa, Victor Facchinetti, Gabriel Oliveira Guimarães Fernandes, Alexandra Mitidieri Bastos Mol Pimentel, Claudia Regina Brandão Gomes, James Lewis Wardell, Solange Maria Silva Veloso Wardell, Marcus Vinicius De Souza
: β-(N-arylamino)acrylates are building blocks of great industrial interest as they allow the obtention of a variety of heterocyclic substances, such as quinoline and pyridone derivatives. Therefore, the development of new methodologies for the synthesis of these substances is still of interest. In this work, fourteen β-(N-arylamino)acrylates were synthesized in a multigram scale from the reaction of mono- and di-substituted anilines with diethyl ethoxymethylenemalonate by sonochemistry (US) and the results compared to those obtained by conventional heating. The use of the US brought many benefits to these syntheses, including faster reactions and increased yields. The crystal structure of diethyl 2-(((2-chloro-5-nitrophenyl)amino)methylene)malonate is also reported.
β-(N-芳基氨基)丙烯酸酯:β-(N-芳基氨基)丙烯酸酯是极具工业价值的构件,因为它们可以获得多种杂环物质,如喹啉和吡啶酮衍生物。因此,开发合成这些物质的新方法仍然很有意义。在这项工作中,利用超声化学(US)技术,通过单取代和二取代苯胺与乙氧基甲叉丙二酸二乙酯的反应,合成了 14 种 β-(N-芳基氨基)丙烯酸酯,并将其结果与传统加热法进行了比较。使用 US 为这些合成带来了许多好处,包括加快反应速度和提高产率。此外,还报告了 2-(((2-氯-5-硝基苯基)氨基)亚甲基)丙二酸二乙酯的晶体结构。
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引用次数: 0
Corrigendum to: Review on Pyrazole Hybrids as Anti-microbial Agents Corrigendum to:吡唑杂化物作为抗微生物剂的综述
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-05-21 DOI: 10.2174/157017862107240520155030
Tanvi Goel, Naman Jain, Deepali Bansode
Similar affiliation error appeared in the author's affiliation in the article entitled “Review on Pyrazole Hybrids as Anti-microbial Agents”, published in Letters in Organic Chemistry, 2024, 21(4), 320-332 [1]. <p> Details of the error and a correction are provided here. <p> Original: <P> Author Affiliation: <sup>1</sup>Department of Pharmaceutical Chemistry, Bharati Vidyapeeth (Deemed to be) University, Poona College of Pharmacy, Pune, India; <sup>2</sup>Department of Pharmaceutical Chemistry, Bharati Vidyapeeth (Deemed to be) University, Poona College of Pharmacy, Pune, India <p> Corrected: <p> Author Affiliation: <sup>1</sup>Department of Pharmaceutical Chemistry, Bharati Vidyapeeth (Deemed to be) University, Poona College of Pharmacy, Pune, India <p> We regret the error and apologize to readers. <p> The original article can be found online at https://www.eurekaselect.com/article/133287
在发表于《有机化学通讯》(Letters in Organic Chemistry)的题为 "Review on Pyrazole Hybrids as Anti-microbial Agents"(《吡唑杂化物作为抗微生物剂综述》)的文章中,作者所属单位出现了类似错误,该文章发表于 2024 年,21(4), 320-332 [1]。<p> 原文: <P> 作者所属单位:<sup>1</sup>Department of Pharmaceutical Chemistry, Bharati Vidyapeeth (Deemed to be) University, Poona College of Pharmacy, Pune, India; <sup>2</sup>Department of Pharmaceutical Chemistry, Bharati Vidyapeeth (Deemed to be) University, Poona College of Pharmacy, Pune, India <p> Corrected:<p>作者所属单位:<sup>1</sup>印度浦那普纳药学院巴拉蒂维迪亚佩斯(已被认定)大学药物化学系<p>我们对错误表示遗憾,并向读者致歉。<p>原文可在 https://www.eurekaselect.com/article/133287 上查阅。
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引用次数: 0
Thiamine Hydrochloride: A Highly Efficient Organo-Catalyst for the One-Pot Synthesis of 2, 4, 5-Triaryl Imidazole Derivatives 盐酸硫胺:一锅合成 2、4、5-三芳基咪唑衍生物的高效有机催化剂
IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2024-05-07 DOI: 10.2174/0115701786268343240427050351
Kishor B. Phatangare, Yatin U. Gadkari, Savita B. Lomte, Simren S. Salim, Vikas N. Telvekar
: In this study, we have developed an expeditious and efficient method for the synthesis of 2,4,5–triaryl imidazole derivatives using thiamine hydrochloride as a catalyst. The one-pot, solventfree- multicomponent reaction of an aromatic/heterocyclic aldehyde with benzyl and ammonium acetate at reflux conditions leads to the formation of title compounds in extremely good yields. This protocol offers several features, such as safe, simple, atom efficient, economical, mild conditions, minimum waste, easy work-up procedures, shorter reaction time (40-45 min), catalyst recyclability, etc. The developed methodology is operationally simple and eco-friendly.
:在这项研究中,我们开发了一种以盐酸硫胺为催化剂合成 2,4,5-三芳基咪唑衍生物的快速高效方法。在回流条件下,芳香族/杂环醛与苄基和乙酸铵发生单锅、无溶剂、多组分反应,生成的标题化合物收率极高。该方法具有安全、简单、原子效率高、经济、条件温和、废物最少、操作简便、反应时间短(40-45 分钟)、催化剂可回收等特点。所开发的方法操作简单、生态友好。
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引用次数: 0
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Letters in Organic Chemistry
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