- A multifunctional triazine-based nanoporous polymer as a versatile organocatalyst for CO2 utilization and C-C bond formation
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A triazine-based nanoporous multifunctional polymer with a SABET of 304 m2 g-1 has shown versatile catalytic activity in the conversion of CO2 to cyclic carbonates at 4 bar with almost 100% yield and selectivity, and in the conversion of CO2 to methanol and methane electrochemically. Additionally, it also catalyzes C-C bond formation via the Knoevenagel reaction.
- Sharma, Ruchi,Bansal, Ankushi,Ramachandran,Mohanty, Paritosh
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- Coordination driven self-assembly of [2 + 2 + 2] molecular squares: Synthesis, crystal structures, catalytic and luminescence properties
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The one-pot self-assembly of three components (metal acetates as the metal precursor, the tridentate polypyridyl ligand, N,N′-bis(2-pyridylmethyl)-tert-butylamine (bpta), as a capping ligand and bent dicarboxylic acids, 4,4′-(dimethylsilanediyl)bis-benzoi
- Gupta, Vijay,Mandal, Sanjay K.
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- Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4-amino-5-cyanopyrimidine) derivatives
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A series of bis(4-amino-5-cyano-pyrimidines) was synthesized and evaluated as dual inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). To further explore the multifunctional properties of the new derivatives, their antioxidant and antibacterial activities were also tested. The results showed that most of these compounds could effectively inhibit AChE and BChE. Particularly, compound 7c exhibited the best AChE inhibitory activity (IC50 = 5.72 ± 1.53 μM), whereas compound 7h was identified as the most potent BChE inhibitor (IC50 = 12.19 ± 0.57 μM). Molecular modeling study revealed that compounds 7c, 7f, and 7b showed a higher inhibitory activity than that of galantamine against both AChE and BChE. Anticholinesterase activity of compounds 7h, 7b, and 7c was significant in vitro and in silico for both enzymes, since these compounds have hydrophobic rings (Br-phenyl, dimethyl, and methoxyphenyl), which bind very well in both sites. In addition to cholinesterase inhibitory activities, these compounds showed different levels of antioxidant activities. Indeed, in the superoxide–dimethyl sulfoxide alkaline assay, compound 7j showed very high inhibition (IC50 = 0.37 ± 0.28 μM). Also, compound 7l exhibited strong and good antibacterial activity against Staphylococcus epidermidis and Staphylococcus aureus, respectively. Taking into account the results of biological evaluation, further modifications will be designed to increase potency on different targets. In this study, the obtained results can be a new starting point for further development of multifunctional agents for the treatment of Alzheimer's disease.
- Boualia, Imen,Derabli, Chamseddine,Boulcina, Raouf,Bensouici, Chawki,Yildirim, Muhammet,Birinci Yildirim, Arzu,Mokrani, El Hassen,Debache, Abdelmadjid
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- Successive oxidation-condensation reactions using a multifunctional gold-supported nanocomposite (Au/MgCe-HDO)
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The application of gold-supported nanocomposites is useful in clinical diagnostics because of their ability to provide bio-compatible and sensitive detection systems. A gold-supported magnesium hydroxide and cerium oxide nanocomposite framework (Au/MgCe-HDO) was synthesized and characterized via XRD, XPS, SEM, DLS, TEM, and TGA techniques. The nanocomposite was used as a selective catalyst for the aerobic oxidation of alcohols under mild reaction conditions followed by successive condensation reactions, like Knoevenagel and Claisen-Schmidt condensation. Substituted benzyl alcohols were converted into the corresponding carbonyl compounds in the presence of the Au/MgCe-HDO nanocomposite with O2 gas and toluene as a solvent. We observed that, upon the addition of malononitrile/ethyl cyanoacetate/acetophenone to the catalyst in the aerobic oxidation reaction, the reaction proceeds to produce the corresponding desired condensation product with up to 95% yield.
- Chandra, Ramesh,Kumar, Loveneesh,Kumar, Rupesh,Sehrawat, Hitesh,Tomar, Ravi,Verma, Nishant
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p. 3472 - 3481
(2022/02/21)
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- Synthesis, molecular docking, and in silico ADME prediction of some fused pyrazolo[1,5-a]pyrimidine and pyrazole derivatives as potential antimicrobial agents
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Twenty compounds of pyrazolo[1,5-a]pyrimidines 14a–j and pyrazole derivatives as Schiff bases 16a–j have been synthesized by the reaction of 5-amino-pyrazole derivatives 9a, b with 2-(arylidene)malononitriles 10a–e or various aldehydes 15a–e, respectively
- Hassan, Ashraf S.,Morsy, Nesrin M.,Awad, Hassan M.,Ragab, Ahmed
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p. 521 - 545
(2021/07/06)
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- Design and Development of Amine Functionalized Mesoporous Cubic Silica Particles: A Recyclable Catalyst for Knoevenagel Condensation
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Abstract: The amine functionalized cubic mesoporous silica nanoparticles (cSiO2-NH2) were successfully synthesized through biphasic stratification approach. The synthesized material was characterised by various spectroscopic and phys
- Gupta, Padmini,Kumar, Lalita S.,Kumar, Yogesh,Shabir, Javaid
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- Introduction of succinimide as a green and sustainable organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b] pyran derivatives
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Aim and Objective: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives
- Hassanzadeh, Fariba,Shirini, Farhad,Mamaghani, Manouchehr,Daneshvar, Nader
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p. 155 - 163
(2021/03/23)
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- Application of structurally enhanced magnetite cored polyamidoamine dendrimer for knoevenagel condensation
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In this paper, the synthesis of magnetic cored amino group terminated dendrimer (Fe3O4@SiO2@PAMAM-G2) through covalent bonding was described. This catalyst was characterized by FT-IR, XRD, FE-SEM, TEM, and TGA d
- Hajizadeh, Fatemeh,Maleki, Behrooz,Zonoz, Farrokhzad Mohammadi,Amiri, Amirhassan
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p. 793 - 804
(2020/10/02)
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- Development of an efficient, one-pot, multicomponent protocol for synthesis of 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives
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A one-pot quick and efficient multicomponent reaction has been developed for the synthesis of a new series of functionalized 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives using 30 mol% ammonium acetate in ethanol as solvent. This economical protocol
- Tabassum, Rukhsana,Ashfaq, Muhammad,Oku, Hiroyuki
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p. 534 - 547
(2020/12/04)
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- Nickel?alkyne?functionalized metal?organic frameworks: An efficient and reusable catalyst
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Electron-donating groups in the robust MOF motif are able to provide an excellent catalytic platform, therefore obtaining site-isolated metal sites. In this study, the terminal alkyne is firstly introduced into UiO-66-type metal-organic frameworks (UiO-66-alkyne). Herein, to further study the application potential of this material, a covalently bonded nickel catalyst based on the alkynyl-tagged UiO-66-alkyne has been prepared and afforded us unprecedented highly dispersed and highly efficient catalytic active species. Meanwhile, this nickel-contained catalyst method for joining metals provided an alternative pathway regarding catalyst designing. With UiO-66-alkyne-Ni, the heterogeneous transformation of homogeneous catalysts is realized. Using benzaldehyde and malononitrile as starting materials, we were able to catalyze the Knoevenagel condensation within 45 min under room temperature with yield (> 99 %). Moreover, the recovery rate of the UiO-66-alkyne-Ni also outperformed previous MOFs in both small-scale and gram-level reactions, which shows UiO-66-alkyne-Ni is a potential contributor to the subsequent industrialization.
- Chen, Huixin,Cheng, Hua,Li, Jilin,Li, Wei,Liao, Shengyun,Liu, Xin,Ning, Liangmin,Shao, Liming,Tang, Siyuan
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- Discovery of Highly Potent Adenosine A1Receptor Agonists: Targeting Positron Emission Tomography Probes
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Adenosine receptor (AR) radiotracers for positron emission tomography (PET) have provided knowledge on the in vivo biodistribution of ARs in the central nervous system (CNS), which is of therapeutic interest for various neuropsychiatric disorders. Additio
- Bakhoda, Abolghasem,Eisenberg, Seth M.,Fowler, Joanna S.,Gao, Zhan-Guo,Guo, Min,Hooker, Jacob M.,Jacobson, Kenneth A.,Javdan, Cameron,Kang, Yeona,Kelleher, Andrew C.,Kim, Sung Won,Li, Yang,O'Conor, Kelly A.,Ramsey, Joseph M.,Rice, Kenner C.,Volkow, Nora D.,Yan, Xuefeng
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- Phosphine-Catalyzed (4 + 2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives
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The δ-sulfonamido-substituted enones were employed as phosphine acceptor in phosphine-catalyzed (4 + 2) annulation of 1,1-dicyanoalkenes. They served as a four-membered synthon to react with 1,1-dicyanoalkenes under mild reaction conditions, producing pip
- Liu, Min,Zhou, Leijie,Shi, Wangyu,Hu, Yimin,Liao, Jianning,Duan, Zeqing,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
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supporting information
p. 7703 - 7707
(2021/10/20)
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- Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
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Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
- Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
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- Amine-functionalized hollow mesoporous nano-bowl with bulky acid-imprinted free space around base sites and DMF-annealed mesoporous channels as an efficient solid base catalyst
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Tailoring free spaces around catalytic sites and constructing inter-connected channels between them are highly attractive for achieving easy accessibility of reactants to catalytic sites. In this study, a strategy for constructing free space around base s
- Li, Shan,Ma, Xuebing,Wei, Shuai,Zhang, Jianing,Zhang, Li
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- Hydroquinone and benzoquinone-catalyzed aqueous Knoevenagel condensation
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A Knoevenagel condensation of various aldehydes with malononitrile effectively proceeded in the presence of hydroquinone/benzoquinone mixed catalysts at room temperature in H2O. Furthermore, γ-deuterium-labeled α,β-unsaturated nitrile derivatives were als
- Koyama, Kaho,Kuwata, Marina,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya,Yamada, Tsuyoshi
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supporting information
p. 6594 - 6597
(2020/09/21)
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- Introduction of a new bis-derivative of succinimide (Bis-Su) as a sustainable and efficient basic organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives under green conditions
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Organo-catalysts have been under great consideration for many years because of their performance and selectivity in the reactions. In this work, a new bis-succinimide (Bis-Su) compound is prepared, identified and used as a green and efficient basic organo
- Hassanzadeh, Fariba,Daneshvar, Nader,Shirini, Farhad,Mamaghani, Manouchehr
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p. 4971 - 4984
(2020/09/02)
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- Photoredox-Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4-Dihydropyridine Approach
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Functionalization with C1-building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C1-molecule, carbon dioxide, makes alternative carboxylation reactions with CO2-surrogates especially important. We report a photoredox-catalyzed protocol for alkene carbamoylations. Readily accessible 4-carboxamido-Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light-mediated single-electron transfer. Addition to various alkenes proceeded with high levels of regio- and chemoselectivity.
- Cardinale, Luana,Konev, Mikhail O.,Jacobi von Wangelin, Axel
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supporting information
p. 8239 - 8243
(2020/06/20)
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- Controllable one-pot synthesis for scaffold diversity: Via visible-light photoredox-catalyzed Giese reaction and further transformation
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This study presents a controllable one-pot synthesis for constructing valuable scaffolds (alcohols, 2,3-dihydrofurans, α-cyano-γ-butyrolactones, and γ-butyrolactones) via a visible-light photoredox-catalyzed Giese reaction and further transformation. This
- Nam, Su Been,Khatun, Nilufa,Kang, Young Woo,Park, Boyoung Y.,Woo, Sang Kook
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supporting information
p. 2873 - 2876
(2020/03/19)
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- Manganese-organic framework assembled by 5-((4′-(tetrazol-5″-yl)benzyl)oxy)isophthalic acid: A solvent-free catalyst for the formation of carbon–carbon bond
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A new three-dimensional manganese-based metal–organic framework Mn4L2(HL)(H2O)5, (1), based on semi-rigid 5-((4′-(tetrazol-5′’-yl)benzyl)oxy)isophthalic acid ligand (H3L) have been prepared and charac
- Jiang, Yansong,Xu, Jianing,Zhu, Ziqian,Jiang, Changwei,Ma, Lin,Wang, Hui,Wang, Li,Fan, Yong
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- Visible-Light Photoredox-Catalyzed α-Regioselective Conjugate Addition of Allyl Groups to Activated Alkenes
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The α-regioselective conjugate addition of allyl groups to activated alkenes is a poorly explored area of research. Herein, we report an α-adduct and (E)-isomer selective conjugate addition of allylsilanes to activated alkenes by visible-light photoredox catalysis. The reaction involves allylic radicals that can be generated from allylsilanes through a photoinduced single-electron transfer mechanism. (Figure presented.).
- Gontala, Arjun,Woo, Sang Kook
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supporting information
p. 3223 - 3228
(2020/07/06)
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- Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides
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An efficient, safe, and environmentally friendly tertiary butyl hydrogen peroxide (TBHP)-mediated rearrangement of aryl/alkylidene malononitrile with anilines has been developed with in situ generation of HCN as the cyanide source for the synthesis of sub
- Bhoite, Shubhangi P.,Bansode, Ajay H.,Suryavanshi, Gurunath
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supporting information
p. 14858 - 14865
(2020/12/02)
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- Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides
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A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.
- Zhang, Dapeng,Lian, Mingming,Liu, Jia,Tang, Shukun,Liu, Guangzhi,Ma, Cunfei,Meng, Qingwei,Peng, Haisheng,Zhu, Daling
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supporting information
p. 2597 - 2601
(2019/04/17)
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- Design and Construction of a Chiral Cd(II)-MOF from Achiral Precursors: Synthesis, Crystal Structure and Catalytic Activity toward C-C and C-N Bond Forming Reactions
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Using achiral components, a V-shaped dicarboxylic acid (H2L) and a conformationally flexible bidentate linker (bpp), a thermally stable chiral metal organic framework {[Cd(bpp)(L)(H2O)]·DMF}n (1), where H2L = 4,
- Gupta, Vijay,Mandal, Sanjay K.
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p. 3219 - 3226
(2019/03/28)
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- Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
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A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit
- Liu, Yingtian,Dang, Xinxin,He, Yu,Bai, Hudong,Chen, Xuehong,Li, Jun-Long,Fan, Junting,Jiang, Hezhong,Li, Jiahong
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p. 662 - 671
(2019/02/20)
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- Amino functionalized Zn/Cd-metal-organic frameworks for selective CO2 adsorption and Knoevenagel condensation reactions
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Two amino functionalized Metal-Organic Frameworks (MOFs), {[Zn(Py2TTz)(2-NH2-BDC)]·(DMF)}n (1) and {[Cd(Py2TTz)(2-NH2-BDC)]·(DMF)·0.5(H2O)}n (2) (where Py2TTz = 2,5-bis(4-pyridyl)thiazolo[5,4-d]thiazole, 2-NH2-BDC = 2-amino-1,4-benzenedicarboxylate, and DMF = N,N-dimethylformamide), were synthesized and characterized using the primary ligand 2-amino-1,4-benzenedicarboxylic acid (2-NH2-H2BDC) and the auxiliary ligand 2,5-bis(4-pyridyl)thiazolo[5,4-d]thiazole (Py2TTz). They possess similar 2-fold interpenetrated three-dimensional bipillared-layer framework structures composed of typical binuclear metal nodes, 2-NH2-BDC two-dimensional layers and Py2TTz bipillars. Notably, thiazole nitrogen atoms and pendant -NH2 groups are present in channels in the two frameworks. Given their good chemical stabilities, high thermal stabilities, and exposed nitrogen sites, gas adsorption and catalytic experiments of the two MOFs were performed. The results demonstrate that MOF 2 can selectively adsorb carbon dioxide gas; moreover, the two MOFs can be employed as recyclable heterogeneous catalysts for Knoevenagel condensation reactions under solvent-free conditions.
- Zhai, Zhi-Wei,Yang, Shuang-Hua,Lv, Ya-Ru,Du, Chen-Xia,Li, Lin-Ke,Zang, Shuang-Quan
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p. 4007 - 4014
(2019/03/26)
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- Access to thiomorpholin-3-one derivatives: [3 + 3]-cycloadditions of α-chlorohydroxamates and 1,4-dithiane-2,5-diol
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A protocol of [3 + 3]-cycloaddition was proposed for the synthesis of 2H-1,4-thiazin-3(4H)-ones and thiomorpholine-3,5-diones from α-chlorohydroxamates and 1,4-dithiane-2,5-diol. This direct and practical method provides a novel and rapid approach for the
- He, Zhao-Lin,Chen, Yi,Wang, Xiaohua,Ni, Mingwang,Wang, Gang
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- Molybdenum carbide as an efficient and durable catalyst for aqueous Knoevenagel condensation
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By following green chemistry principles, various molybdenum compounds as cost-effective, commercially available, heterogeneous, and benign catalysts were used for the Knoevenagel condensation reaction. Among the compounds (Mo2C, MoS2, MoB, MoSi2), molybdenum carbide showed efficient performance for the Knoevenagel condensation in aqueous media at room temperature, affording the corresponding products in high yields within a short reaction time. Notably, using this commercially available heterogeneous catalyst, the deacetalization-Knoevenagel condensation of benzaldehyde dimethyl acetal and malononitrile at room temperature could successfully proceed in excellent yield. Molybdenum carbide could be recovered five times without loss of activity with an operationally simple procedure.
- Tavakolian, Mina,Najafpour, Mohammad Mahdi
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p. 16437 - 16440
(2019/11/11)
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- Asymmetric Organocatalytic Michael Addition-Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles
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An asymmetric organocatalytic cascade reaction between cyclopentane-1,2-diones and alkylidene malononitriles affords highly substituted 4 H-pyrans in moderate to high enantiomeric excess. The selective reduction of a bridged double bond leads to the forma
- J?rving, Ivar,Kaabel, Sandra,Kanger, T?nis,Silm, Estelle
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p. 4198 - 4204
(2019/11/14)
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- Nitrogen enriched polytriazine as a metal-free heterogeneous catalyst for the Knoevenagel reaction under mild conditions
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A nitrogen enriched (52 wt%) nanoporous polytriazine with a high specific surface area up to 850 m2 g-1 was synthesized by an ultra-fast (30 min reaction time) microwave assisted route using the inexpensive precursors cyanuric chlori
- Chaudhary, Monika,Mohanty, Paritosh
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p. 12924 - 12928
(2018/08/01)
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- Rapid and efficient uncatalyzed knoevenagel condensations from binary mixture of ethanol and water
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This paper presents a new green protocol for Knoevenagel condensations of aldehydes and compounds with an active methylene group in a binary mixture of ethanol/water (3:7, v/v). This medium favored the uncatalyzed Knoevenagel reactions and easy workup pro
- Ferreira, Jo?o M. G. O.,De Resende Filho, Jo?o B. M.,Batista, Poliane K.,Teotonio, Ercules E. S.,Vale, Juliana A.
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p. 1382 - 1387
(2018/06/12)
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- Layered double hydroxide anchored ionic liquids as amphiphilic heterogeneous catalysts for the Knoevenagel condensation reaction
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In recent years, great attention has been dedicated to the development of heterogeneous base catalysts providing a green and sustainable process in benign aqueous media. Herein, the ionic liquid modified layered double hydroxide (LDH) based catalysts of L
- Li, Tengfei,Zhang, Wei,Chen, Wei,Miras, Haralampos N.,Song, Yu-Fei
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p. 3059 - 3067
(2018/03/06)
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- Protic Ionic Liquid Promoted One Pot Synthesis of 2-amino-4-(phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile Derivatives in Water and Their Antimycobacterial Activity
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One pot three component reaction of 4-hydroxy-6-methylpyran-2-one, 3-methoxy benzaldehyde, and malononitrile in water using protic ionic liquid as a catalyst at room temperature afforded pyrano[4,3-b]pyran derivatives. Protic ionic liquid has been proved
- Mohire, Priyanka P.,Chandam, Dattatray R.,Patil, Reshma B.,Kumbhar, Digambar R.,Jadhav, Sunetra J.,Patravale, Ajinkya A.,Godase, Vijaya P.,Ghosh, Jai S.,Deshmukh, Madhukar B.
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p. 1010 - 1023
(2018/04/24)
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- Water assisted and choline chloride-dimethylurea deep eutectic salts as catalyst towards the attractive reaction of indole, benzaldehyde, and malononitrile
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The condensation of indole, benzaldehyde, and malononitrile was relatively rigorous compared with other Yonemitsu type reaction. We described a strategy using catalytic amount of choline chloride-dimethylurea deep eutectic salts as cheap and safe accelerator. We also found that introducing right amount of water in reaction system was crucial. This method tolerates variations in all three components to get desired 3-substituted indoles in satisfactory yields.
- Ruan, Hongli,Lv, Yue,Yu, Shijun,Lv, Chengwei,An, Yue
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p. 1266 - 1274
(2018/08/06)
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- Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents
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A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids,-butyrolactones, and complex aryl alkyl ethers.
- Khatun, Nilufa,Kim, Myeong Jun,Woo, Sang Kook
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supporting information
p. 6239 - 6243
(2018/09/27)
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- Preclinical Evaluation of the First Adenosine A1 Receptor Partial Agonist Radioligand for Positron Emission Tomography Imaging
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Central adenosine A1 receptor (A1R) is implicated in pain, sleep, substance use disorders, and neurodegenerative diseases, and is an important target for pharmaceutical development. Radiotracers for A1R positron emission t
- Guo, Min,Gao, Zhan-Guo,Tyler, Ryan,Stodden, Tyler,Li, Yang,Ramsey, Joseph,Zhao, Wen-Jing,Wang, Gene-Jack,Wiers, Corinde E.,Fowler, Joanna S.,Rice, Kenner C.,Jacobson, Kenneth A.,Kim, Sung Won,Volkow, Nora D.
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p. 9966 - 9975
(2018/11/23)
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- Synthesis and characterization of bromine source immobilized on diethylenetriamine-functionalized magnetic nanoparticles: A novel, versatile and highly efficient reusable catalyst for organic synthesis
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Bromine source immobilized on magnetic nanoparticles functionalized with diethylenetriamine was successfully synthesized and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, vibrating sample magnetometry, thermogravimetric analysis and X-ray diffraction. The catalytic activity in the synthesis of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives and in Knoevenagel condensation was studied. The bromine catalyst can be magnetically recovered and reused several times without significant loss of its catalytic activity. All products were obtained in high to excellent yields.
- Shiri, Lotfi,Rahmati, Sadegh,Ramezani Nejad, Zahra,Kazemi, Mosstafa
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- Fe3O4–cysteamine hydrochloride magnetic nanoparticles: New, efficient and recoverable nanocatalyst for Knoevenagel condensation reaction
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Fe3O4 magnetic nanoparticles (MNPs) were obtained using a reduction–precipitation method. These MNPs were modified with cysteamine hydrochloride. This catalyst was characterized using a number of physicochemical measurements. The Fe
- Maleki, Razieh,Kolvari, Eskandar,Salehi, Mehdi,Koukabi, Nadiya
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- Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions
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The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.
- Xu, Gang,Wang, Lu,Li, Mengmeng,Tao, Minli,Zhang, Wenqin
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supporting information
p. 5818 - 5830
(2017/12/26)
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- Preparation of a superior liquid catalyst by hybridization of three solids of nanoZnO, urea, and choline chloride for Knoevenagel-based reactions
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Abstract: The complex catalyst of [ZnClO.urea]?[Ch.urea]+ has been prepared by dissolving of nanoZnO in choline chloride:2urea at 50 °C. The concentration of [ZnClO.urea]? in the given liquid is 19,987 ppm and 10.5 times h
- Tamaddon, Fatemeh,Azadi, Davood
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p. 2077 - 2086
(2017/09/13)
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- Magnetic Fe3O4 nanoparticles supported amine: a new, sustainable and environmentally benign catalyst for condensation reactions
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Abstract: Diethylenetriamine immobilized on magnetic Fe3O4 nanoparticles (DETA-Fe3O4) was successfully prepared as a new and well dispersed magnetically separable amine catalyst. The structure of the resulting catalyst was well characterized by a series of analysis techniques such as FT-IR, SEM, EDX, VSM, TGA and XRD. The catalytic activity of DETA-Fe3O4 was evaluated with Knoevenagel condensation of active methylene compounds with aromatic aldehydes. Interestingly, the cyclocondensation of anthranilamide and aldehydes were effectively catalyzed by DETA-Fe3O4 in water, and the desired products (2,3-dihydroquinazoline-4(1H)-ones) were afforded in admirable yields. Catalysis research under aqueous medium (water) also makes this synthetic protocol ideal and fascinating from the environmental point of view. The amine catalyst can be magnetically recovered after the reaction and can be reused many times without appreciable decrease in activity.
- Shiri, Lotfi,Kazemi, Mosstafa
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p. 4813 - 4832
(2017/07/22)
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- Synthesis and characterization of bromine source supported on magnetic Fe3O4 nanoparticles: A new, versatile and efficient magnetically separable catalyst for organic synthesis
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Tribenzylammonium tribromide supported onto magnetic nanoparticles (Br3-TBA-Fe3O4) as a bromine source was successfully synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy and vibrating sample magnetometry. The synthesized catalyst is shown to be a versatile and highly efficient heterogeneous catalyst for the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-one and polyhydroquinoline derivatives. To the best of the authors' knowledge, this is the first report of the use of a bromine source immobilized on Fe3O4 nanoparticles as a magnetically separable catalyst for these reactions. The nanosolid catalyst can be magnetically recovered and reused readily several times without significant loss in catalytic efficiency.
- Shiri, Lotfi,Ghorbani-Choghamarani, Arash,Kazemi, Mosstafa
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- Effective and Green One-Pot Multicomponent Synthesis of Novel Derivatives of 4H-Pyrans in the Presence of Hexamethylenetetramine as Catalyst in Water Medium
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Hexamethylenetetramine catalyzes synthesis of new polyfunctionalized 4H-pyrans by the reaction of aromatic aldehyde, malononitrile, and β-keto esters via one-pot three-component procedure in water medium. Addition of reactants was performed by two methods
- Habibi, Maysam,Habibi, Azizollah,Hakimi Nasab, Saber,Dolati, Hadi,Mahdavi, Seyedeh Mahbobeh
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p. 1598 - 1603
(2017/03/27)
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- RETRACTED ARTICLE: Effective and Green One-Pot Multicomponent Synthesis of Novel Derivatives of 4H-Pyrans in the Presence of Hexamethylenetetramine as Catalyst in Water Medium
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Hexamethylenetetramine (HMTA) catalyzes synthesis of new polyfunctionalized 4H-pyrans by reaction of aromatic aldehyde, malononitrile, and β-keto esters via one-pot three-component procedure in water medium. Addition of reactants was performed by two meth
- Habibi, Maysam,Habibi, Azizollah,Hakimi Nasab, Saber,Dolati, Hadi,Mahdavi, Seyedeh Mahbobeh
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p. 1880 - 1886
(2017/05/29)
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- Metal-free visible light driven synthesis of tetrahydroquinoline derivatives utilizing Rose Bengal
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The visible-light driven reaction for the synthesis of tetrahydroquinoline derivatives via tandem radical cyclization of N,N-dimethylanilines with 2-benzylidenemalononitriles has been developed. Corresponding products were obtained with yields of up to 74
- Xin, Jing-Rui,Guo, Jun-Tao,Vigliaturo, Dominic,He, Yan-Hong,Guan, Zhi
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p. 4627 - 4633
(2017/07/11)
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- N-heterocyclic carbene-promoted [3+2] cycloaddition of allenyl sulfone and arylidenemalononitriles
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N-Heterocyclic carbenes promote the [3+2] cycloaddition of allenyl sulfone and arylidenemalononitriles, accompanied by 1,2-migration of the sulfonyl group. This reaction provides a new route to highly substituted cyclopentenes.
- Kuwano, Satoru,Masuda, Toshinobu,Yamaguchi, Koki,Arai, Takayoshi
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p. 232 - 242
(2017/07/28)
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- Electrochemical approach for synthesis of 3-substituted indole derivatives
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An efficient and economical method was developed for synthesis of 3-substituted indole by using electrochemically induced condensation of various aldehyde, indole and malononitrile.
- Singh, Vinay K.,Dubey, Rahul,Upadhyay, Abhishek,Sharma, Laxmi Kant,Singh, Rana Krishna Pal
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supporting information
p. 4227 - 4231
(2017/10/12)
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- Pd(0)@UiO-68-AP: Chelation-directed bifunctional heterogeneous catalyst for stepwise organic transformations
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A bifunctional heterogeneous catalyst Pd(0)@UiO-68-AP based on a chelation-directed post-synthetic approach is reported. It exhibits typical heterogeneous catalytic behaviour and can promote benzyl alcohol oxidiation-Knoevenagel condensation in a stepwise way.
- Li, Yan-An,Yang, Song,Liu, Qi-Kui,Chen, Gong-Jun,Ma, Jian-Ping,Dong, Yu-Bin
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p. 6517 - 6520
(2016/06/01)
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- Au@Cu(II)-MOF: Highly Efficient Bifunctional Heterogeneous Catalyst for Successive Oxidation-Condensation Reactions
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A new composite Au@Cu(II)-MOF catalyst has been synthesized via solution impregnation and full characterized by HRTEM, SEM-EDS, XRD, gas adsorption-desorption, XPS, and ICP analysis. It has been shown here that the Cu(II)-framework can be a useful platform to stabilize and support gold nanoparticles (Au NPs). The obtained Au@Cu(II)-MOF exhibits a bifunctional catalytic behavior and is able to promote selective aerobic benzyl alcohol oxidation-Knoevenagel condensation in a stepwise way.
- Wang, Jing-Si,Jin, Fa-Zheng,Ma, Hui-Chao,Li, Xiao-Bo,Liu, Ming-Yang,Kan, Jing-Lan,Chen, Gong-Jun,Dong, Yu-Bin
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p. 6685 - 6691
(2016/07/16)
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- The synthesis of a bifunctional copper metal organic framework and its application in the aerobic oxidation/Knoevenagel condensation sequential reaction
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A novel one-pot aerobic oxidation/Knoevenagel condensation reaction system was developed employing a Cu(ii)/amine bifunctional, basic metal-organic framework (MOF) as the catalyst. The sequential aerobic alcohol oxidation/Knoevenagel condensation reaction was efficiently promoted by the Cu3TATAT MOF catalyst in the absence of basic additives. The benzylidenemalononitrile product was produced in high yield and selectivity from an inexpensive benzyl alcohol starting material under an oxygen atmosphere. The role of the basic functionality was studied to demonstrate its role in the aerobic oxidation and Knoevenagel condensation reactions. The reaction progress was monitored in order to identify the reaction intermediate and follow the accumulation of the desired product. Lastly, results showed that the yield was not significantly compromised by the reuse of a batch of catalyst, even after more than five cycles.
- Miao, Zongcheng,Luan, Yi,Qi, Chao,Ramella, Daniele
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supporting information
p. 13917 - 13924
(2016/09/09)
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