- Synthesis and anticancer activity of novel tetrahydroquinoline and tetrahydropyrimidoquinoline derivatives
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A series of new tetrahydroquinolines with different substituents at C-2 and C-4 positions in addition to several tetrahydropyrimidoquinolin-4-amines and tetrahydropyrimidoquinoline-2,4-diamines were synthesized. The in vitro anticancer activity of all new
- Gedawy, Ehab M.,Kassab, Asmaa E.,El-Malah, Afaf A.
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- Seven new Zn(II)/Cd(II) coordination polymers with 2-(hydroxymethyl)-1H-benzo[d]imidazole-5-carboxylic acid: Synthesis, structures and properties
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Using a new simi-rigid multitopic ligand 2-(hydroxymethyl)-1H-benzo[d]imidazole-5-carboxylic acid (H2L), seven new coordination polymers [Zn3(L)2(μ2-OH)2]n (1), {[Zn2(HL)2/
- Wang, Xin-Fang,Zhou, Sheng-Bin,Du, Ceng-Ceng,Wang, Duo-Zhi,Jia, Dianzeng
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- Catalyst-free one-pot synthesis and antioxidant evaluation of highly functionalized novel 1,4-dihydropyridine derivatives
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A catalyst-free greener protocol for the most effective one-pot synthesis of 2,6-diamino-4-aryl-1-propyl/cyclohexyl-1,4-dihydropyridine-3,5-dicarbonitrile derivatives has been developed using a simple three-component reaction of structurally diverse aldeh
- Ramesh, Rathinam,Maheswari, Subramani,Murugesan, Senniappan,Sandhiya, Raman,Lalitha, Appaswami
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- Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes with cyano and amino groups
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The first synthesis of 5,12-diamino-7,14-bis(aryl)-1,4,8,11-tetrathiacyclotetradeca-5,12-diene-6,13-dicarbonitriles was performed as a multicomponent macroheterocyclization of malononitrile, aryl aldehydes, and 1,2-ethanedithiol in the presence of a catal
- Akhmadiev, Nail S.,Akhmetova, Vnira R.,Ibragimov, Askhat G.,Mescheryakova, Ekaterina S.
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- Mixed Metal-Organic Framework as a Heterogeneous Catalyst
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The synthesis of a new mixed metal-organic framework (M′MOF) has been accomplished by the metalloligand approach. [NaCu(2,4-HPdc)(2,4-Pdc)] (2,4-H2Pdc = pyridine-2,4-dicarboxylic acid) has been obtained from the hydrothermal reaction of the metalloligand [Cu(2,4-HPdc)2(H2O)2] NaOH, and a transition metal salt. [NaCu(2,4-HPdc)(2,4-Pdc)] is isostructural to [CuMn(2,4-Pdc)2] and crystallizes in the triclinic space group Pβar {1}$. The 3D structure is built up from [Cu(2,4-HPdc)2(H2O)2] metalloligands and [NaO6] octahedra in a pcu α-Po-like uninodal six-connected net. The compound is stable to 290 °C, and its crystal structure undergoes a 3 % volume expansion between room temperature and thermal decomposition. The unsaturated CuII centers at the surface act as a heterogeneous Lewis acid catalyst for the cyanosilylation of aldehydes and Knoevenagel C-C bond-forming reactions. The catalytic activity has been compared with those of other copper(II) porous metal-organic frameworks such as HKUST-1 and MOF-74.
- Larrea, Edurne S.,Fernández De Luis, Roberto,Orive, Joseba,Iglesias, Marta,Arriortua, María I.
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- Green approach for Knoevenagel condensation of aromatic aldehydes with active methylene group
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An ecofriendly and economical method of Knoevenagel condensation of aromatic aldehydes with malononitrile catalyzed by lemon juice, a natural catalyst, in the absence of any solvent is described. Copyright Taylor & Francis Group, LLC.
- Deshmukh,Patil, Suresh S.,Jadhav,Pawar
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- Significant Gas Adsorption and Catalytic Performance by a Robust CuII-MOF Derived through Single-Crystal to Single-Crystal Transmetalation of a Thermally Less-Stable ZnII-MOF
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By using a bent tetracarboxylic acid ligand that incorporates a pendent -NH2 functional group, a 3D ZnII-framework (1) based on Zn2(CO2)4 secondary building units and Zn12(CO2)s
- Pal, Tapan K.,De, Dinesh,Neogi, Subhadip,Pachfule, Pradip,Senthilkumar,Xu, Qiang,Bharadwaj, Parimal K.
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- Multistep Synthesis of Fluorine-Substituted Pyrazolopyrimidine Derivatives With Higher Antibacterial Efficacy Based on In Vitro Molecular Docking and Density Functional Theory
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Some new fluorine-substituted pyrazolopyrimidine derivatives (1.3–1.5) have been synthesized by the multistep reactions, starting from reaction of 4-fluorophenyl malanonitrile (1) with guanidine, followed by ring closure reaction with hydrazine to give 2,
- Khan, Salman A.,Asiri, Abdullah M.,Rahman,Elroby, Shaaban A.,Aqlan, Faisal M. S.,Wani, Mohmmad Y.,Sharma, Kamlesh
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- Synthesis of two metal-porphyrin frameworks assembled from porphyrin building motifs, 5, 10, 15, 20-tetrapyridylporphyrin and their base catalyzed property
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Opening catalytically active sites in metal organic frameworks is an issue of fundamental importance for the development of effective and efficient catalysts. In this work, we first reported two metal metalloporphyrin-organic frameworks (MMPFs) with unocc
- Zhang, Weijie,Jiang, Pingping,Wang, Ying,Zhang, Jian,Zhang, Pingbo
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- Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO2and deacetalization-Knoevenagel condensation
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Herein, the rare combination of BaII (5s) and ZnII (3d) in the presence of the structure-oriented TDP6- ligand generated the nanochannel-based hybrid material {[(CH3)2NH2]2[BaZn(TDP)(H2O)]·DMF·5H2O}n (NUC-51, H6TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochemical characteristics such as nanoscopic channels, high porosity, large specific surface area, and high heat/water-resistance. To the best of our knowledge, this is the first 3D [BaIIZnII(CO2)6(H2O)]-based nano-porous host framework, whose activated state possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn2+ ions, 7-coordinated Ba2+ ions, uncoordinated carboxyl oxygen atoms, and Npyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO2 at 55 °C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70 °C.
- Chen, Hongtai,Fan, Liming,Gao, Yanpeng,Lv, Hongxiao,Zhang, Xiutang
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p. 3546 - 3556
(2022/03/14)
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- Nanochannel {InZn}-Organic Framework with a High Catalytic Performance on CO2Chemical Fixation and Deacetalization-Knoevenagel Condensation
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The rare combination of InIII 5p and ZnII 3d in the presence of a structure-oriented TDP6- ligand led to a robust hybrid material of {(Me2NH2)[InZn(TDP)(OH2)]·4DMF·4H2O}n (NUC-42) with the interlaced hierarchical nanochannels (hexagonal and cylindrical) shaped by six rows of undocumented [InZn(CO2)6(OH2)] clusters, which represented the first 5p-3d nanochannel-based heterometallic metal-organic framework. With respect to the multifarious symbiotic Lewis acid-base and Br?nsted acid sites in the high porous framework, the catalytic performance of activated NUC-42a upon CO2 cycloaddition with styrene oxide was evaluated under solvent-free conditions with 1 atm of CO2 pressure, which exhibited that the reaction could be well completed at ambient temperature within 48 h or at 60 °C within 4 h with high yield and selectivity. Moreover, because of the acidic function of metal sites and a central free pyridine in the TDP6- ligand, deacetalization-Knoevenagel condensation of acetals and malononitrile could be efficiently facilitated by an activated sample of NUC-42a under lukewarm conditions.
- Chen, Hongtai,Zhang, Zhengguo,Hu, Tuoping,Zhang, Xiutang
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p. 16429 - 16438
(2021/11/01)
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- A ru-complex tethered to a N-rich covalent triazine framework for tandem aerobic oxidation-knoevenagel condensation reactions
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Herein, a highly N-rich covalent triazine framework (CTF) is applied as support for a RuIII complex. The bipyridine sites within the CTF provide excellent anchoring points for the [Ru(acac)2(CH3CN)2]PF6 complex. The obtained robust RuIII@bipy-CTF material was applied for the selective tandem aerobic oxidation-Knoevenagel condensation reaction. The presented system shows a high catalytic performance (>80% conversion of alcohols to α, β-unsaturated nitriles) without the use of expensive noble metals. The bipy-CTF not only acts as the catalyst support but also provides the active sites for both aerobic oxidation and Knoevenagel condensation reactions. This work highlights a new perspective for the development of highly efficient and robust heterogeneous catalysts applying CTFs for cascade catalysis.
- Abednatanzi, Sara,Der Voort, Pascal Van,Derakhshandeh, Parviz Gohari,Leus, Karen,Schmidt, Johannes,Watson, Geert
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- Biguanide-functionalized hierarchical porous covalent organic frameworks for efficient catalysis of condensation reactions
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Covalent organic frameworks (COFs) can be rationally designed with desired physicochemical properties for a far-ranging application in catalytic systems. Herein, a biguanide-functionalized covalent organic framework was designed and prepared via N-alkylat
- Feng, Huiru,Gong, Kai,Li, Cunhao,Li, Haoran,Wang, Yunyun,Zhang, Daquan,Zhang, Huimin
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- Ferrocene-Functionalized Dithiocarbamate Zinc(II) Complexes as Efficient Bifunctional Catalysts for the One-Pot Synthesis of Chromene and Imidazopyrimidine Derivatives via Knoevenagel Condensation Reaction
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Four new mononuclear/coordination polymeric (CP) zinc(II) complexes (1-4) of ferrocenyl/pyridyl-functionalized dithiocarbamate ligands, N-ferrocenylmethyl-N-butyl dithiocarbamate (L1), N-ferrocenylmethyl-N-ethylmorpholine dithiocarbamate (L2), N-ferroceny
- Anamika,Drew, Michael G. B.,Kumar, Kamlesh,Singh, Nanhai,Yadav, Chote Lal
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p. 6446 - 6462
(2021/05/31)
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- Knoevenagel condensation in aqueous media promoted by 2,2′-bipyridinium dihydrogen phosphate as a green efficient catalyst
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A 2,2′-Bipyridine-based ionic compound named 2,2′-bipyridinium dihydrogen phosphate was synthesized by addition of phosphoric acid to a solution of 2,2′-Bipyridine in dichloromethane. After the characterization using FT-IR, mass, 1H, 13C and 31P NMR techniques, it was used as a Bronsted dicationic acidic catalyst for the promotion of the synthesis of 2-arylidene malononitrile and 5-arylidene barbituric acid derivatives via Knoevenagel condensation reaction in water. Some of the advantages of this method are the utilization of an easy preparable, cost-effective and eco-friendly organic salt as a catalyst within high rates and yields of the reactions, simple and quick work-up and acceptable reusability of the catalyst.
- Darvishzad, Shila,Daneshvar, Nader,Shirini, Farhad,Tajik, Hassan
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p. 2973 - 2984
(2021/04/19)
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- Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds
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First copper(I) chalcogenones catalysed Knoevenagel Condensation reactions have been reported. No illustration of the utilization of this copper-chalcogenone complex class in Knoevenagel Condensation catalysis can be found. Thus, copper(I) bis(benzimidazole-2-chalcogenone) catalysts [Cu(L1)4]+BF4? (1) and [Cu(L2)4]+BF4? (2) (L1 = bis(1-isopropyl-benzimidazole-2-selone)-3-ethyl; L2 = bis(1-isopropyl-benzimidazole-2-thione)-3-ethyl) have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent catalytic activity has been depicted for various types of substrates with either electron-rich or deficient aryl aldehydes. The present investigation features relatively mild reaction conditions with good functional group tolerance and excellent yields. Graphic Abstract: The first copper(I)-chalcogenone complexes catalysed Knoevenagel Condensation reactions?have also been investigated, and revealed the best catalytic activities. [Figure not available: see fulltext.]
- Mannarsamy, Maruthupandi,Prabusankar, Ganesan
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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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- Introduction of bis-imidazolium dihydrogen phosphate as a new green acidic ionic liquid catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives
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In this work, [H2-Bisim][H2PO4]2 as a novel bis-imidazole-based acidic ionic liquid has been synthesized and characterized with a variety of techniques including FT-IR, 1H, 13C, 31/su
- Rahmatizadeh-Pashaki, Zahra,Daneshvar, Nader,Shirini, Farhad
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p. 2135 - 2149
(2021/02/01)
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- A 2D-layered Cd(II) MOF as an efficient heterogeneous catalyst for the Knoevenagel reaction
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A Cd(II) coordination polymer based on a polytopic compartmental ligand was synthesized, and used as an efficient heterogeneous catalyst for the Knoevenagel reaction between benzaldehyde and malononitrile under mild reaction conditions. The solid catalyst
- Tom, Lincy,Kurup
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- One-pot oxidant-free dehydrogenation-Knoevenagel tandem reaction catalyzed by a recyclable magnetic base-metal bifunctional catalyst
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A new base-metal bifunctional catalyst NH-Pd(0)@MNP was prepared via a facile procedure and fully characterized. The as-prepared catalyst was used as an efficient relay catalyst for the one-pot oxidant-free dehydrogenation-Knoevenagel condensation tandem reaction from benzyl alcohol in H2O under mild conditions and generated benzalmalononitriles with yield up to 96%. Meanwhile, the catalyst could be easily recovered from the reaction system by an external magnetic field, and is reusable with little loss of activity up to 6 runs (5%).
- Yuan, Xiaofeng,Wan, Zijuan,Ning, Jinfeng,Zhang, Qiang,Luo, Jun
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- Synthesis, crystal structure and catalytic property of a highly stable 3D Cu(II)-organic framework
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A three-dimensional (3D) Cu(II)-based MOF, [CuL·Cl]n (namely complex 1), was successfully generated through the in-situ reaction of CuCl2, NaN3, and 4-(4-cyanostyryl)pyridine. Notably, –CN and N3 ? ca
- Chen, Chunyan
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- An excellently stable heterovalent copper–organic framework based on Cu4I4 and Cu(COO)2N2 SBUs: The catalytic performance for CO2 cycloaddition reaction and Knoevenagel condensation reaction
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A novel 3D heterovalent Cu-based MOF, [Cu2Cu4I4(ANA)4(DMF)4]n (denoted as complex 1), was successfully designed and synthesized by the self-assembly of CuI and 5-aminonicotinic acid (HANA)
- Jin, Feng
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- Assembly of Two Self-Interpenetrating Metal-Organic Frameworks Based on a Trigonal Ligand: Syntheses, Crystal Structures, and Properties
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Two self-interpenetrating metal-organic frameworks (MOFs) 1 and 2 were designed and constructed through the coordination self-assembly of transition metal nodes and a trigonal ligand. They both exhibit interesting three-dimensional constructions with the
- Fan, Yuhang,Guo, Feng,Shi, Wenbing,Su, Changhua,Zhang, Xiuling
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- Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes
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Five novel zinc(II) and cadmium(II) β-oxodithioester complexes, [Zn(L1)2] (1), [Zn(L2)2]n (2), [Zn(L3)2]n (3) [Cd(L1)2]n (4), [Cd(L2)2]n (5), with β-oxodithioester ligands, where L1 = 3-(methylthio)-1-(thiophen-2-yl)-3-thioxoprop-1-en-1-olate, L2 = 3-(methylthio)-1-(pyridin-3-yl)-3-thioxoprop-1-en-1-olate, and L3 = 3-(methylthio)-1-(pyridin-4-yl)-3-thioxoprop-1-en-1-olate, were synthesized and characterized by elemental analysis, IR, UV-vis, and NMR spectroscopy (1H and 13C{1H}). The solid-state structures of all complexes were ascertained by single-crystal X-ray crystallography. The β-oxodithioester ligands are bonded to Zn(II)/Cd(II) metal ions in an Oa§S and N chelating/chelating-bridging fashion leading to the formation of 1D (in 2-4) and 2D (in 5) coordination polymeric structures, but complex 1 was obtained as a discrete tetrahedral molecule. Complex 4 crystallizes in the C2 chiral space group and has been studied using circular dichroism (CD) spectroscopy. The multidimensional assemblies in these complexes are stabilized by many important noncovalent C-H···π(ZnOSC3, chelate), ?···?, C-H···?, and H···H interactions. The catalytic activities of 1-5 in reactions involving C-C and C-O bond formation have been studied, and the results indicated that complex 3 can be efficiently utilized as a heterogeneous bifunctional catalyst for the Knoevenagel condensation and multicomponent reactions to develop biologically important organic molecules. The luminescent properties of complexes were also studied. Interestingly, zinc complexes 1-3 showed strong lumniscent emission in the solid state, whereas cadmium complexes 4 and 5 exhibited bright luminescent emission in the solution phase. The semiconducting behavior of the complexes was studied by solid-state diffuse reflectance spectra (DRS), which showed optical band gaps in the range of 2.49-2.62 eV.
- Anamika,Drew, Michael G. B.,Kumar, Kamlesh,Rajput, Gunjan,Singh, Nanhai,Yadav, Chote Lal
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supporting information
(2020/09/09)
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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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- 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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- COMPOUNDS AND METHODS FOR TREATING OR PREVENTING HEART FAILURE
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The present invention relates to the discovery of novel compounds that can be used to treat and/or prevent heart failure in a subject. In certain embodiments, the compounds of the invention are sulfide: quinone oxidoreductase (SQOR) inhibitors. In other e
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Page/Page column 104
(2020/07/25)
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- Method for catalyzing benzal malononitrile compound by SBA-15 supported ionic liquid
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The invention provides a method for catalyzing a benzal malononitrile compound by SBA-15 supported ionic liquid. The method comprises the following steps: putting malononitrile, aryl aldehyde and an SBA-15 supported ionic liquid catalyst into a reaction c
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Paragraph 0049-0050
(2020/07/02)
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- Catalysis through Dynamic Spacer Installation of Multivariate Functionalities in Metal-Organic Frameworks
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We demonstrate herein a facile strategy to engineer versatile catalytically active coordination interspace in the same primitive metal-organic framework (MOF) for variable heterogeneous catalysis. Different functional ligands can be reversibly inserted into and removed from proto-LIFM-28 individually or successively to bring in single or binary catalytic sites for specific reactions and switch the parent MOF to multipurpose catalysts. Alcohol-oxidation, Knoevenagel-condensation, click, acetal, and Baylis-Hillman reactions are achievable through simple exchange of a single catalytic spacer, while sequential or stepwise reactions are designable via selective combination of two catalytic spacers with different functionalities, thus making proto-LIFM-28 a multivariate MOF for multiuse and economic catalysis.
- Cao, Chen-Chen,Chen, Cheng-Xia,Wei, Zhang-Wen,Qiu, Qian-Feng,Zhu, Neng-Xiu,Xiong, Yang-Yang,Jiang, Ji-Jun,Wang, Dawei,Su, Cheng-Yong
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p. 2589 - 2593
(2019/03/04)
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- Method used for preparing substituted 1, 3-malononitrile
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The invention belongs to the field of fine chemical product preparation and medicine intermediate synthesis, and relates to a method used for preparing substituted 1, 3-malononitrile. According to themethod, an aldehyde or a ketone and malononitrile are subjected to condensation reaction to prepare substituted 1, 3-malononitrile, wherein water is taken as a solvent, the aldehyde or the ketone andmalononitrile are subjected to Knoevenagel condensation under catalytic effect of zinc proline so as to obtain the corresponding substituted 1, 3-malononitrile. The method conditions are mild; operation is convenient; water is taken as a reaction solvent, so that the method is friendly to the environment; and the application prospect is promising.
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Paragraph 0030-0031
(2019/08/07)
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- New magnetic nanocatalyst containing a bis-dicationic ionic liquid framework for Knoevenagel condensation reaction
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Bis[(3-aminopropyl)triethoxysilane]dichloride immobilized on magnetic nano-γ-Fe2O3@SiO2 has been prepared. After characterization, the reagent was used for efficient promotion of the Knoevenagel reaction, achieving high re
- Karimi-Chayjani, Reyhaneh,Daneshvar, Nader,Shirini, Farhad,Tajik, Hassan
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p. 2471 - 2488
(2019/02/24)
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- Synthesis, structure, and catalytic properties of a copper(II) coordination polymer material constructed from 5-nitro-1,2,3-benzenetricarboxylic acid and bis(4-pyridylformyl)piperazine mixed ligands
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One three-dimensional coordination polymer material, {[Cu3(nbta)2(bpfp)2(H2O)2](H2O)2}n (H3nbta = 5-nitro-1,2,3-benzenetricarboxylic acid, bpfp = bis(4-pyri
- Li, Zhao-Hao,Xue, Li-Ping,Qin, Qiu-Pei,Zhao, Yi-Jing
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- Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature
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Abstract: Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with malononitrile and ethyl cyanoacetate. The reaction proceeds at room temperature without using any organic solvent and is very fast with good to excellent yield. Additionally, the catalyst is easily separable and recyclable without loss of activity. Graphic Abstract: [Figure not available: see fulltext.].
- Burate, Pralhad A.,Javle, Balasaheb R.,Desale, Pranjal H.,Kinage, Anil K.
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p. 2368 - 2375
(2019/06/17)
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- The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions
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The Knoevenagel condensation between active methylene compounds and aromatic carobonyl compounds has been developed using quinine as an organocatalyst to afford various electrophilic alkenes in excellent yields (up to 90%). In the presence of a catalytic amount of quinine (15 mol%), the reaction proceeded at room temperature (RT) under solvent-free conditions. In this green approach, the organocatalyst was recovered and recycled for up to four cycles without appreciable loss of activity.
- Jain, Kavita,Chaudhuri, Saikat,Pal, Kuntal,Das, Kalpataru
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supporting information
p. 1299 - 1304
(2019/01/21)
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- Janus Interphase Organic-Inorganic Hybrid Materials: Novel Water-Friendly Heterogeneous Catalysts
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In this work, amphiphilic silica-based Janus-type acid and base catalysts are introduced as heterogeneous analogues of surfactants. The new interphase organic-inorganic hybrid catalysts comprise of two different groups (?C8H17, ?Csu
- Vafaeezadeh, Majid,Breuninger, Paul,L?sch, Philipp,Wilhelm, Christian,Ernst, Stefan,Antonyuk, Sergiy,Thiel, Werner R.
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p. 2304 - 2312
(2019/04/17)
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- Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes
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A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 molpercent PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
- Mangaonkar, Saeesh R.,Singh, Fateh V.
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p. 4473 - 4486
(2019/11/21)
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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 and anticholinesterase activity of novel non-hepatotoxic naphthyridine-11-amine derivatives
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Abstract: In the present study, 14 novel naphthyridine-11-amine derivatives were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 12-(4-Fluorophenyl)-1,2,3,4,7,8,9,10-octahydrodibenz
- Zengin Kurt, Belma
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p. 625 - 638
(2018/12/11)
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- Synthesis and characterization of sulfamic acid supported on Fe3O4 nanoparticles: A green, versatile and magnetically separable acidic catalyst for oxidation reactions and Knoevenagel condensation
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Sulfamic acid immobilized on diethylenetriamine functionalized Fe3O4 nanoparticles (SA-DETA-Fe3O4) was successfully prepared and characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), vibrating sample magnetometer (VSM), thermo gravimetric analysis (TGA), X-Ray diffraction (XRD) and scanning electron microscopy (SEM). The sulfamic acid was found as a magnetically separable and highly active catalyst for the oxidative coupling thiols, oxidation of sulfides. Furthermore, the SA-DETA-Fe3O4 showed the high catalytic activity in Knoevenagel condensation of aromatic aldehydes with active methylene compounds (malononitrile and ethyl cynoacetate). The nanosolid catalyst could be easily recovered by a simple magnetic separation and reused for many cycles without deterioration in catalytic activity.
- Shiri, Lotfi,Narimani, Hojatollah,Kazemi, Mosstafa
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- Synthesis method of alkenyl dinitrile compounds
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The invention discloses a synthesis method of alkenyl dinitrile compounds. The preparation method comprises the following steps: taking substituted aldehyde and malononitrile as raw materials, takingRu/C as a catalyst, carrying out a reaction at 20-60 DEG
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Paragraph 0071-0074
(2018/09/08)
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- Knoevenagel reaction catalyzed by a reusable Br?nsted acid based on 1-alkyl-1, 2, 4-triazolium tetrafluoroborate
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The Knoevenagel reaction is one of the most useful methods for the synthesis of α, β- unsaturated nitriles. We disclose an efficient protocol for the Knoevenagel reaction of aldehydes with malononitrile catalyzed by 1-alkyl-1, 2, 4-triazolium salts to aff
- Kandasamy, Elango,Nagarajan, Sankaranarayanan,Shaikh, Tanveer M.
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supporting information
p. 133 - 138
(2018/03/06)
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- Construction of two Zn(ii)/Cd(ii) multifunctional coordination polymers with mixed ligands for catalytic and sensing properties
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With the purpose of exploring the catalytic and sensing properties of crystalline materials, two coordination polymers were rationally constructed by the reactions of Zn(ii)/Cd(ii) ions with methyl-3-hydroxy-5-carboxy-2-thiophenecarboxylate (H2
- Xue, Li-Ping,Li, Zhao-Hao,Zhang, Ting,Cui, Jia-Jia,Gao, Yue,Yao, Jia-Xin
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p. 14203 - 14209
(2018/08/28)
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- TEDETA@BNPs as a basic and metal free nanocatalyst for Knoevenagel condensation and Hantzsch reaction
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In this work, Boehmite nanoparticles (BNPs) were synthesized in water using commercially available materials and further N,N,N′,N′-tetraethyldiethylentriamin (TEDETA) was supported on the surface of BNPs, and used as organo-basic catalyst in four-componen
- Ghorbani-Choghamarani, Arash,Heidarnezhad, Zahra,Tahmasbi, Bahman,Azadi, Gouhar
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p. 2281 - 2293
(2018/08/28)
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- Sulfuric acid heterogenized on magnetic Fe3O4 nanoparticles: A new and efficient magnetically reusable catalyst for condensation reactions
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Immobilized sulfuric acid on magnetic Fe3O4 nanoparticles (Fe3O4 MNPs-OSO3H) as a new solid acid nanocomposite was successfully synthesized and its catalytic activity in a series of condensation reactions was studied. High catalytic activity, simple separation from reaction mixture by an external magnet and good reusability are several eco-friendly advantages of this catalytic system. It is noteworthy that this catalytic system is applicable to a wide range of spectrum of aromatic aldehydes, and the desired products were obtained in good to excellent yields under mild conditions. The use of ecofriendly solvents makes also this synthetic protocol ideal and fascinating from the environmental point of view.
- Shiri, Lotfi,Zarei, Setare,Kazemi, Mosstafa,Sheikh, Davood
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- Ultrasound-assisted rapid synthesis of β-cyanoepoxides using hypervalent iodine reagents
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An elegant approach for the rapid synthesis of β-cyanoepoxides 3 by the epoxidation of β-cyanostyrenes 1 with PIDA 2a is described. The epoxidation of β-cyanostyrenes 1 was performed with 1.2 equiv. of PIDA 2a in MeCN-H2O (1:1) at room temperature in ultrasonic bath. The epoxidation reactions were completed in short reaction time and β-cyanoepoxides 3 were isolated in 69–94% yields.
- Singh, Fateh V.,Mangaonkar, Saeesh R.,Kole, Priyanka B.
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supporting information
p. 2169 - 2176
(2018/07/21)
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- One-pot synthesis of [1,2,4]Triazolo[1,5-a]pyridines from azines and benzylidenemalononitriles via copper-catalyzed tandem cyclization
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A simple and efficient copper-catalyzed tandem radical cyclization reaction has been discovered for the synthesis of triaryl [1,2,4]triazolo[1,5-a]pyridines from easily accessible azines and benzylidenmalononitriles. The new transformation involves multip
- Lv, Jianguang,He, Zhiqing,Zhang, Jianmin,Guo, Yuwei,Han, Ziwei,Bao, Xinhua
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supporting information
p. 3996 - 4004
(2018/06/20)
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- Syntheses, crystal structures and knoevenagel condensation reactions of three coordination polymers assembled with Lewis basic ligand
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Three functional coordination polymers (CPs), [(CH3)2NH2]2[Cd3L2(H2O)2]·6H2O (1), [Ba4L2(H2O)8]·H2O (
- Ma, Li,Wu, Hua,Yang, Jin,Liu, Ying-Ying,Ma, Jian-Fang
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- A novel bifunctional Pd-ZIF-8/rGO catalyst with spatially separated active sites for the tandem Knoevenagel condensation-reduction reaction
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A novel bifunctional catalyst with spatially separated active sites was prepared by the immobilization of Pd nanoparticles (NPs) via covalent interaction and coordination of a zeolitic imidazolate framework (ZIF-8) on the surface of graphene oxide (GO), respectively, which was used as an efficient catalyst for the Knoevenagel condensation-reduction tandem reaction. The results of Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), Raman spectroscopy, UV-vis spectroscopy, X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) demonstrated that Pd and ZIF-8 were successfully immobilized on the surface of GO, and the GO was reduced to reduced graphene oxide (rGO) using NaBH4 as the reductant in the preparation of Pd-ZIF-8/rGO. The textural properties and morphology of Pd-ZIF-8/rGO were characterized by N2 adsorption-desorption, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Pd-ZIF-8/rGO shows excellent catalytic performance in the tandem reaction with 100% benzaldehyde conversion and 98.3% selectivity to benzylmalononitrile. The excellent catalytic performance of Pd-ZIF-8/rGO in the tandem reaction is due to the high catalytic activities of spatially separated Pd NPs and ZIF-8 active sites and concentrated reactants on the surface of Pd-ZIF-8/rGO due to the π-π interaction between rGO and the reactants. The anchoring and stabilization effects of oxygenated groups of GO inhibit the aggregation and leakage of active sites, leading to good catalytic recyclability with almost unchanged catalytic activity for more than eight cycles in the tandem reaction.
- Wang, Hefang,Wang, Yansu,Jia, Aizhong,Wang, Cunyue,Wu, Luming,Yang, Yongfang,Wang, Yanji
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p. 5572 - 5584
(2017/12/07)
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- H3PW12O40/mpg-C3N4 as an efficient and reusable bifunctional catalyst in one-pot oxidation-Knoevenagel condensation tandem reaction
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A single-site bifunctional catalyst for the oxidation-Knoevenagel condensation tandem reaction was prepared by the immobilization of phosphotungstic acid (HPW) on mesoporous graphitic carbon nitride (mpg-C3N4) via electrostatic interaction (HPW/mpg-C3N4). The results of Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), solid-state 31P nuclear magnetic resonance (solid-state 31P NMR), zeta potentials, X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) demonstrated that HPW was successfully immobilized on the protonated mpg-C3N4 by electrostatic interaction. The acid amounts of the catalysts were determined by NH3 temperature programmed desorption (NH3-TPD). The textural properties and morphology of HPW/mpg-C3N4 were characterized by N2 adsorption-desorption, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). 30% HPW/mpg-C3N4 shows the best catalytic performance in the tandem reaction with 98.4% benzyl alcohol conversion and 96.2% selectivity to benzylidene malononitrile. The excellent catalytic performance of 30% HPW/mpg-C3N4 in the tandem reaction is due to the good catalytic performance of HPW in the oxidation and Knoevenagel condensation, respectively. Furthermore, protonated mpg-C3N4 not only acts as a support to facilitate good dispersion of HPW but also promotes the Knoevenagel condensation reaction effectively. Moreover, the HPW/mpg-C3N4 catalyst could be recycled easily without significant loss of catalytic activity.
- Wang, Hefang,Wang, Cunyue,Yang, Yongfang,Zhao, Meng,Wang, Yanji
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p. 405 - 417
(2017/08/14)
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- Knoevenagel condensation catalyzed by novel Nmm-based ionic liquids in water
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A series of novel N-methyl morpholine (Nmm) based ionic liquids with 1,2-propanediol group were synthesized and used as catalysts for Knoevenagel condensation at room temperature in water. Under the effect of the catalyst, various aldehydes or aliphatic ketones could react with a wide range of activated methylene compounds well, including malononitrile, alkyl cyanoacetate, cyanoacetamide, β-diketone, barbituric acid, 2-arylacetonitrile and thiazolidinedione. Furthermore, most of the products could be separated just by filtrating and washing with water. Additionally, the catalyst is recyclable and applicable for the large-scale synthesis.
- Xu, Hao,Pan, Liyang,Fang, Xiaomin,Liu, Baoying,Zhang, Wenkai,Lu, Minghua,Xu, Yuanqing,Ding, Tao,Chang, Haibo
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supporting information
p. 2360 - 2365
(2017/05/29)
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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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- 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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- A Simple and straightforward synthesis of cinnamic acids and ylidene malononitriles via knoevenagel condensation employing dabco as catalyst
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An efficient method for the synthesis of substituted cinnamic acid and ylidene malanonitriles is developed via Knoevenagel condensation of aromatic aldehydes with malonic acid and malononitrile in the presence of catalytic amounts of DABCO. This method has many advantages, such as mild reaction conditions, excellent yields, short reaction times and no furthur purification required.
- Nagalakshmi,Diwakar,Govindh,Gopal Reddy,Venu,Bhargavi,Prasanna Devi,Murthy,Siddaiah
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p. 1561 - 1564
(2017/05/29)
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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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- Knoevenagel condensation reaction catalysed by Al-MOFs with CAU-1 and CAU-10-type structures
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The metal-organic frameworks (MOFs) CAU-1-NH2 ([Al4(OH)2(OCH3)4(p-BDC-NH2)3], (p-BDC-NH2)2- = 2-aminoterephthalate) and CAU-10-NH2 ([Al(OH)(m-BDC-NH2)], (m-BDC-NH2)2- = 5-aminoisophthalate) which possess two different pore sizes were studied for their catalytic activity as heterogeneous solid base catalysts in the Knoevenagel condensation reaction between benzaldehyde and malononitrile under mild reaction conditions (40 °C, 7 h, ethanol). For comparison, isoreticular MOFs containing a smaller amount of -NH2 groups (CAU-1-NH2/H) or no -NH2 groups (CAU-10-H) were synthesized. A two-step synthesis route including the synthesis of CAU-1-NH2 and its use as crystal seeds was developed to obtain the mixed-linker CAU-1-NH2/H compound. Only for CAU-1-NH2, up to 100% selectivity towards the desired Knoevenagel condensation product is observed. Hence, the catalytic activity of CAU-1-NH2 was tested between various benzaldehydes containing different substituents with malononitrile. By employing benzaldehyde and malononitrile as the starting materials, it is found that the mixed-linker MOF CAU-1-NH2/H catalyses the formation of the acetal (benzaldehyde diethyl acetal), while both CAU-10 materials lead to mixtures of the two products. Furthermore, the catalyst stability was also examined through reusability and leaching experiments and it is observed that the catalyst can be reused with no significant drop in its activity.
- Dhakshinamoorthy, Amarajothi,Heidenreich, Niclas,Lenzen, Dirk,Stock, Norbert
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p. 4187 - 4193
(2017/08/04)
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- Porous hierarchical magnesium oxide-based heterogeneous catalyst for the Knoevenagel condensation
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Herein, an operationally facile and efficient Knoevenagel reaction catalyzed by porous hierarchical MgO/Mg(OH)2 is presented. Condensation of various aldehydes with malononitrile proceeds under mild conditions and gives the target products with
- Deilami,Sayyahi
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p. 1085 - 1086
(2017/06/29)
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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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