- Photoacid as ICT probe for ground state proton transfer process from solute to solvents
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In present work, 2-(4-Hydroxybenzylidene)malononitrile (HyDC) acts as a photoacid and intramolecular charge transfer (ICT) probe for monitoring solvent specific ground state proton transfer (GSPT) process from solute to solvents. Presence of electron accepting group in HyDC, photoacidic nature and GSPT process are enhanced and observed by UV–Vis spectroscopy. HyDC shows microsolvation behavior with protic solvents at ground state. Microsolvated clusters of HyDC with solvents are formed and supported by experimental and theoretical results.
- Panja, Sumit Kumar
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Read Online
- Elementary and efficient catalyst process for the Knoevenagel condensation of araldehydes with arylmethylidene malononitrile
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A comparative study of the Knoevenagel condensation of an aromatic aldehyde with an active methylene compound (e.g., malononitrile or ethyl cyanoacetate), using solvent free grindstone conditions and microwave irradiation is reported. Our solvent free app
- Jlassi, Raja,Ribeiro, Ana P.C.,Tiago, Gon?alo A.O.,Wang, Jiawei,Krawczyk, Marta S.,Martins,Na?li, Houcine,Pombeiro, Armando J.L.,Rekik, Walid
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Read Online
- Supported copper on a diamide-diacid-bridged PMO: an efficient hybrid catalyst for the cascade oxidation of benzyl alcohols/Knoevenagel condensation
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In this study, a novel periodic mesoporous organosilica (PMO) containing diamide-diacid bridges was conveniently prepared using ethylenediaminetetraacetic dianhydride to support Cu(ii) species and affording supramolecular Cu@EDTAD-PMO nanoparticles efficiently. Fourier transform infrared (FT-IR) and energy dispersive X-ray (EDX) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), Brunauer-Emmett-Teller (BET) analysis, and high-resolution transmission electron microscopy (HRTEM) results confirmed the successful synthesis of Cu@EDTAD-PMO. The stabilized Cu(ii) nanoparticles inside the mesochannels of the new PMO provided appropriate sites for selective oxidation of different benzyl alcohol derivatives to their corresponding benzaldehydes and subsequent Knoevenagel condensation with malononitrile. Therefore, Cu@EDTAD-PMO can be considered as a multifunctional heterogeneous catalyst, which is prepared easily through a green procedure and demonstrates appropriate stability with almost no leaching of the Cu(ii) nanoparticles into the reaction medium, and easy recovery through simple filtration. The recycled Cu@EDTAD-PMO was reused up to five times without significant loss of its catalytic activity. The stability, recoverability, and reusability of the designed heterogeneous catalyst were also studied under various reaction conditions.
- Dekamin, Mohammad G.,Valiey, Ehsan
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p. 437 - 450
(2022/01/20)
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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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- 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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- Effect of supramolecular polymeric aggregation in room temperature ionic liquids (RTILs) on catalytic activity in the synthesis of 4H-chromene derivatives and Knoevenagel condensation
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RTILs exhibit supramolecular self-assembled polymeric aggregation due to noncovalent interactions. The influence of the aggregation behaviour of RTILs on catalytic activity is evident but still poorly understood. The present work focuses on establishing a
- Muhammad, Shoaib,Ali, Firdous Imran,Javed, Muhammad Naveed,Wasim, Agha Arsalan,Bari, Ahmed,Rafique, Faisal,Ilyas, Muhammad Amjad,Riaz, Kashif,Mahmood, Syed Junaid,Ahmed, Amir,Hashmi, Imran Ali
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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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- Magnetic core-shell dendritic mesoporous silica nanospheres anchored with diamine as an efficient and recyclable base catalyst
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In the present study, diamine-functionalized magnetic core-shell dendritic mesoporous silica nanospheres have been successfully synthesized by an oil-water biphasic stratification-coating strategy. The shape, size and morphology of the synthesized magnetic nanocatalyst could be characterized by various physicochemical techniques such as, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM). The characteristic information about the successful immobilization of various functionalities on the nanospheres could be obtained with the help of X-ray powder diffraction (XRD) patterns, Fourier transform-infrared spectroscopy (FT-IR), energy dispersive X-ray spectroscopy (EDX) and thermo-gravimetric analysis (TGA). The details about the magnetic behaviour and surface area of the nanocatalyst could be acquired by vibrating sample magnetometry (VSM) and BET surface analysis, respectively. The synthesized diamine-functionalized magnetic nanoparticles were then explored as a highly efficient catalyst for the Knoevenagel condensation and one-pot synthesis of polyhydroquinolines using aromatic/heteroaromatic aldehydes and aliphatic aldehydes with active methylene compounds under very mild conditions. The synthesized magnetic core-shell dendritic mesoporous silica nanospheres had large surface areas. This large surface area and pore volume could facilitate a proper interaction and penetration of the reactant molecules with the basic amine groups present on the dendritic mesoporous silica nanospheres. The supported nanocatalyst revealed no sign of leaching of the amine groups present inside the dendrimers and therefore, could be reused up to nine times without any noteworthy loss in catalytic activity.
- Surabhi,Shabir, Javaid,Gupta, Padmini,Sah, Digvijay,Mozumdar, Subho
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p. 21152 - 21166
(2020/12/31)
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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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- 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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- 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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- Synthesis of structurally enhanced magnetite cored poly(propyleneimine) dendrimer nanohybrid material and evaluation of its functionality in sustainable catalysis of condensation reactions
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The conventional method of dendrimer synthesis especially poly(propyleneimine) dendrimer (PPI) involves complicated reaction workup and tedious separation strategies. Since it has greater number of nitrogen atom in their structure, its applications are in
- Kannappan, Lakshmi,Rajmohan, Rangasamy
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- Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds
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In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.
- Falah, Saeid,Soleiman-Beigi, Mohammad,Kohzadi, Homa
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- Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives
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—An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chrome
- Zabihzadeh, Mehdi,Omidi, Atefeh,Shirini, Farhad,Tajik, Hassan,Langarudi, Mohaddeseh Safarpoor Nikoo
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- A facile microwave-assisted Knoevenagel condensation of various aldehydes and ketones using amine-functionalized metal organic frameworks
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An amine-functionalized metal organic framework (MOF) was used as highly efficient and recyclable heterogeneous catalyst for Knoevenagel condensation of various aromatic aldehydes and ketones in ethanol. The catalytic efficiency was demonstrated by the hi
- Lee, Ik-Mo,Lumbiny, Bilkis Jahan,Taher, Abu
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- Bismuth (III) Triflate: A Mild, Efficient Promoter for the Synthesis of Trisubstituted Alkenes through Knoevenagel Condensation
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In this work, smooth efficient and eco-friendly two component coupling method is reported for the synthesis of Knoevenagel Condensation product in presence of Bi(OTf)3 catalyst under solvent free condition. Catalyst has participated in condensation between substituted aldehydes (aromatic and hetero-aromatic) and active methylene compounds (ethyl cyanoacetate, malononitrile and cyanoacetamide) effectively to generate an excellent yield of the product. Bi(OTf)3 catalyst is stable, inexpensive and easily available was used for four times in this reaction without loss of catalytic activity. [Formula Presented]
- Datta, Arup
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p. 843 - 849
(2020/11/25)
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- Magnetically recoverable 2-(aminomethyl)phenols-modified nanoparticles as a catalyst for Knoevenagel condensation and carrier for palladium to catalytic Suzuki coupling reactions
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A class of magnetic nanoparticles modified by 2-(aminomethyl)phenols has been successfully designed and synthesized as a reusable catalyst for Knoevenagel reaction. What's more, such nanomaterial also proved as suitable carrier for immobilization of palladium nanoparticles and the obtained composite exerted potent catalytic activity in Suzuki coupling reactions. Both of the (aminomethyl)phenols-modified nanoparticles and its related palladium nanocatalyst could be easily separated and reused for several consecutive runs by magnetic decantation without significant loss of their catalytic efficiency.
- Wang, Gongshu,Ding, Zhiqiang,Meng, Lingxin,Yan, Guiyang,Chen, Zhangpei,Hu, Jianshe
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- An Efficient and Reusable Multifunctional Composite Magnetic Nanocatalyst for Knoevenagel Condensation
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A range of multifunctional magnetic metal-organic framework nanomaterials consisting of various mass ratios of the metal-organic framework MIL-53(Fe) and magnetic SiO 2 @NiFe 2 O 4 nanoparticles were designed, prepared, ch
- Yao, Nan,Tan, Jin,Liu, Yang,Hu, Yu Lin
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supporting information
p. 699 - 702
(2019/03/26)
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- Calcined Dolomite: An Efficient and Recyclable Catalyst for Synthesis of Α, Β-Unsaturated Carbonyl Compounds
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Abstract: Calcined dolomite was utilized as a low-cost and efficient catalyst for the Knoevenagel condensation of aldehydes with active methylene compounds such as malononitrile and ethyl cyanoacetate to afford substituted α, β-unsaturated carbonyl compou
- Yang, Hongyuan,Dong, Hao,Zhang, Tengfei,Zhang, Qi,Zhang, Guangwei,Wang, Peng,Liu, Qing
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p. 778 - 787
(2019/01/04)
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- Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations
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In the present work, 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) dichloride ([C4(MIm)2]·2Cl) and 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate ([C4(MIm)2]·2HSO4) were prepared via adequate, solvent-free methods and characterized using FT-IR, 1H NMR, 13C NMR, and potentiometric titration techniques. These reagents were investigated in the synthesis of 5-arylidene (thio)barbituric acids, 2-arylidene malononitriles, 4H-pyrans, and pyrano[2,3-d] pyrimidineones, and their catalytic activities were compared in the promotion of these reactions. Based on the obtained results, we found that [C4(MIm)2]·2Cl showed more catalytic efficiency where a basic or weak acidic media is needed. In contrast, [C4(MIm)2]·2HSO4 is a powerful catalyst in reactions needing acidic catalysts to enhance the reaction rate. Using these reagents, the products were formed under mild and eco-friendly conditions in excellent yields during short reaction times without needing column chromatography for work-up.
- Sharifi, Zahra,Daneshvar, Nader,Langarudi, Mohaddeseh Safarpoor Nikoo,Shirini, Farhad
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p. 4941 - 4958
(2019/07/03)
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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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- A Zn based metal organic framework as a heterogeneous catalyst for C-C bond formation reactions
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Herein, we report the synthesis and application of a Zn-Bp-BTC MOF (Bp-4,4′-bipyridine; BTC-1,3,5-benzene tricarboxylic acid; MOF-metal organic framework) as a heterogeneous catalyst for mediating organic reactions. Initially, conditions were optimized for the Knoevenagel condensation reaction using Zn-Bp-BTC as a heterogeneous catalyst by varying the solvent, temperature and catalyst loading. Although the reaction proceeded at room temperature using methanol as the solvent, 60 °C offered the best yield in a shorter duration. Under optimized reaction conditions, a wide range of α,β-unsaturated dicyano compounds were prepared from the corresponding carbonyl precursor and malononitrile, the active methylene counterpart. Systematic investigation was also carried out to assess the role of the ligand and metal salt in the Knoevenagel condensation reaction. It was found that the Zn-Bp-BTC MOF catalyzed the reaction efficiently in comparison to its analogue Zn-BTC MOF and precursor Zn(NO3)2·6H2O. Finally, catalytic recycling and stability studies showed that the catalyst is able to mediate the reaction for up to five consecutive cycles without undergoing any significant chemical or morphological changes. Further, the catalyst was tested for its efficacy in a multi-component reaction (MCR). A MCR with the Zn-Bp-BTC MOF as the catalyst afforded good yields and there was no reaction in the absence of the catalyst. Similarly, the catalyst was tested for its efficiency in benzimidazole synthesis.
- Madasamy, Kanagaraj,Kumaraguru, Shanmugasundaram,Sankar, Velayutham,Mannathan, Subramaniyan,Kathiresan, Murugavel
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p. 3795 - 3800
(2019/03/05)
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- Mechanically fabricated Metal–organic framework/resin composite nanoparticles for efficient basic catalysis
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Zeolitic imidazolate framework-8 (ZIF-8) was successfully composited with an anionic basic resin 201?×?7 (717-resin) to provide a novel ZIF-8/717-resin composite. Its catalytic activity toward the Knoevenagel condensation reaction was evaluated. Results s
- Zhang, Zhi-Hui,Qian, Bing-Bing,Sheng, Pan-Pan,Yang, Sen,Huang, Xian-Feng,Wang, Jin-Long,Chen, Qun,Wang, Liang,He, Ming-Yang
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- An efficient and recyclable acid-base bifunctional core-shell nano-catalyst for the one-pot deacetalization-Knoevenagel tandem reaction
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A novel magnetic nanoparticle supported acid-base bifunctional catalyst was synthesized by anchoring [3-(2-aminoethyl)aminopropyl]triethoxysilane and sulfonic acid successively onto the surface of silica-coated Fe3O4 nanoparticles. The as-prepared nanoparticle catalyst was used as a quasi-homogeneous and recyclable catalyst for the one-pot deacetalization-Knoevenagel tandem reaction of benzaldehyde dimethylacetals and malononitrile. It showed high catalytic activity because the reaction proceeded smoothly and afforded benzylidenemalononitriles in excellent yields. Besides, it showed synergistic effect and facilitated the mass transfer process during the tandem reaction because the two catalytic moieties were connected together on the same MNP. Moreover, the catalyst can be readily recovered under an external magnetic field and reused without any significant loss of the catalytic activity after six runs.
- Wang, Zitao,Yuan, Xiaofeng,Cheng, Qi'An,Zhang, Tichun,Luo, Jun
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p. 11610 - 11615
(2018/07/24)
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- Efficient and recyclable novel Ni-based metal–organic framework nanostructure as catalyst for the cascade reaction of alcohol oxidation–Knoevenagel condensation
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A novel Ni-based metal–organic framework (Ni-MOF) with a Schiff base ligand as an organic linker, Ni3(bdda)2(OAc)2?6H2O (H2bdda?=?4,4′-[benzene-1,4-diylbis(methylylidenenitrilo)]dibenzoic acid), was synthesized and characterized using powder X-ray powder diffraction, thermogravimetric analysis, Brunauer–Emmett–Teller measurements, inductively coupled plasma atomic emission spectroscopy, transmission electron microscopy, elemental analysis and Fourier transform infrared spectroscopy. The synthesized Ni-MOF exhibited a high catalytic activity in benzyl alcohol oxidation using tert-butyl hydroperoxide under solvent-free conditions. Also, the efficiency of the catalyst was investigated in the cascade reaction of oxidation–Knoevanagel condensation under mild conditions. The Ni-MOF catalyst could be recovered and reused four times without significant reduction in its catalytic activity.
- Aryanejad, Sima,Bagherzade, Ghodsieh,Farrokhi, Alireza
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- Efficient Synthesis of Branched Polyamine Based Thermally Stable Heterogeneous Catalyst for Knoevenagel Condensation at Room Temperature
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Abstract: In this paper, a new convenient strategy for the synthesis of polyethylenimine functionalized Si-MCM-41 grafted on surface modified graphene oxide has been developed. The as-synthesised catalyst exerts good catalytic activity and reusability tow
- Chaudhuri, Haribandhu,Gupta, Radha,Dash, Subhajit
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p. 1703 - 1713
(2018/04/02)
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- Development of Amine Functionalized Wrinkled Silica Nanospheres and Their Application as Efficient and Recyclable Solid Base Catalyst
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Abstract: Amine functionalized wrinkled silica nanospheres (WSiO2–NH2) were successfully synthesized by using a simple biphase sol–gel approach. The prepared silica nanospheres were characterized by using various techniques, such as
- Shabir, Javaid,Garkoti, Charu,Surabhi,Sah, Digvijay,Mozumdar, Subho
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p. 194 - 204
(2017/11/20)
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- An efficient Knoevenagel condensation of aldehydes with active methylene compounds over novel, robust CeZrO4?δ catalyst
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Abstract: In the present work, we explored novel CeZrO4?δ as a catalyst for Knoevenagel condensation of aldehydes with reactive methylene compounds like malononitrile and ethylcyanoacetate. For the present study, ceria, zirconia and CeZrO4
- Sahani, Amber J.,Burange, Anand S.,Jayaram, Radha V.
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p. 7805 - 7814
(2018/09/12)
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- Fe3O4-Methylene diphenyl diisocyanate-guanidine (Fe3O4–4,4′-MDI-Gn): A novel superparamagnetic powerful basic and recyclable nanocatalyst as an efficient heterogeneous catalyst for the Knoevenagel condensation a
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In this paper, guanidine groups (Gn) supported on modified magnetic nanoparticles (Fe3O4–4,4′-MDI) were synthesized for the first time. The catalyst synthesized was characterized by various techniques such as SEM (Scanning Electron M
- Maleki, Razieh,Koukabi, Nadiya,Kolvari, Eskandar
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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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- Bifunctional 2D Cd(II)-Based Metal-Organic Framework as Efficient Heterogeneous Catalyst for the Formation of C-C Bond
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A porous two-dimensional (2D) metal-organic framework (MOF), namely, [Cd(PBA)(DMF)]·DMF (Cd-PBA), has been solvothermally synthesized by the reaction of 5-(4-pyridin-3-yl-benzoylamino)-isophthalic acid ligand (H2PBA) and Cd(II) ions. Structural
- Hu, Lei,Hao, Gui-Xia,Luo, Hai-Dong,Ke, Chun-Xian,Shi, Guang,Lin, Jia,Lin, Xiao-Ming,Qazi, Umair Yaqub,Cai, Yue-Peng
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p. 2883 - 2889
(2018/05/09)
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- Tungstate-loaded triazine-based magnetic poly(Bis-imidazolium ionic liquid): An effective bi-functional catalyst for tandem selective oxidation/Knoevenagel condensation in water
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A novel bi-functional polymeric catalyst was synthesized by immobilization of tungstate anions onto the nitrogen rich poly(ionic liquid)/magnetic nanocomposite. The resulting catalyst has two types of catalytic sites: (i) immobilized WO4 anions with bis-imidazolium ionic liquid cation for selective oxidation of alcohols and (ii) basic amine groups for Knoevenagel condensation between produced aldehyde and malononitrile. Due to the polymeric nature of the catalyst, large amounts of tungstate and basic nitrogen groups were presented on the solid surface which led to a decrease in the applied catalyst mass for catalytic reaction. High catalytic activity and excellent selectivity of catalyst in water medium make this protocol a green way for production of fine chemicals.
- Zohreh, Nasrin,Tavakolizadeh, Maryam,Hosseini, Seyed Hassan,Pourjavadi, Ali,Bennett, Craig
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p. 342 - 350
(2017/02/19)
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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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- 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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- 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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- 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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- Mn-MOF@Pi composite: synthesis, characterisation and an efficient catalyst for the Knoevenagel condensation reaction
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We have synthesised new Mn-MOF@Pi composite by encapsulation of piperidine in desolvated Mn-MOF and investigated its catalytic performance in Knoevenagel condensation reaction. The newly developed composite is compatible with various aromatic aldehydes an
- Rambabu, Darsi,Ashraf, Mohammad,Pooja,Gupta, Ankush,Dhir, Abhimanew
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supporting information
p. 4691 - 4694
(2017/11/17)
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- Green synthesis of a nano salt and its application as multifunctional organocatalyst for Knoevenagel condensation
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1,2-Ethanediammonium 3-hydroxypropane-1-sulfonate [(EDA)(HPS)] as a novel nano multifunctional organosalt was synthesized via a simple and green chemical route and characterized using various techniques such as proton nuclear magnetic resonance (1/s
- Honarmand, Moones
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p. 6421 - 6432
(2017/10/05)
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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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- New facile, eco-friendly and rapid synthesis of trisubstituted alkenes using bismuth nitrate as lewis acid
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Background: For the synthesis of tri and tetra-substituted alkenes, Knoevenagel condensations have previously been performed in solvents like dichloromethane, DMF, toluene, acetonitrile, DMSO etc. These conditions suffer from certain limitations like long
- Muhammad, Munira T.,Khan, Khalid M.,Taha, Muhammad,Khan, Tariq,Hussain, Shafqat,Fakhri, Muhammad I.,Perveen, Shahnaz,Voelter, Wolfgang
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p. 231 - 235
(2016/03/01)
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- Synthesis and biocatalytic ene-reduction of Knoevenagel condensation compounds by the marine-derived fungus Penicillium citrinum CBMAI 1186
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The chemoselective bioreduction of α,β-unsaturated compounds is an important synthetic tool that can have applications in the synthesis of many fine chemicals and pharmaceutical molecules. The synthesis of aromatic malononitrile derivatives through Knoevenagel condensation by microwave radiation under green chemistry conditions using methanol like solvent, free base and free catalyst is here reported. In addiction the biocatalytic reduction of the C–C double bond of aromatic malononitrile derivatives by whole cells of the marine-derived fungal Penicillium citrinum CBMAI 1186 was also tested. The products catalyzed by the fungus ene-reductase were obtained in very good yields (up to >98%).
- Jimenez, David E.Q.,Ferreira, Irlon M.,Birolli, Willian G.,Fonseca, Luis P.,Porto, André L.M.
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p. 7317 - 7322
(2016/10/29)
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- Tailoring a magnetically separable NiFe2O4nanoparticle catalyst for Knoevenagel condensation
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A magnetically separable NiFe2O4nanoparticle catalyst was prepared readily via a simple one-step hydrothermal process. The catalytic performance of this hetero-nanostructure was investigated by Kneovenagel condensation with aldehydes
- Li, Qichen,Wang, Xiaozhong,Yu, Yanyun,Chen, Yingqi,Dai, Liyan
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p. 8358 - 8363
(2016/12/02)
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- Introduction of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst for the promotion of organic reactions under green conditions
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Taurine (2-aminoethanesulfonic acid), a semi-essential amino acid that exists in the human body and numerous other living creatures, is used as a green bio-organic catalyst for the promotion of the Knoevenagel reaction between aldehydes and malononitrile. In the same way, tetraketones can also be produced through a Knoevenagel reaction, followed by Michael addition. 2-Amino-3-cyano-4H-pyran derivatives are simply prepared via a three-component reaction in the presence of taurine as the catalyst. All these reactions are performed in water, a green solvent. The advantages of using of taurine as the catalyst are it is environmentally friendly, low cost, commercially available, easy to separate from the reaction mixture, and has high reusability. Use of this catalyst results in acceptable reaction times, high yields and high purities of the obtained products without utilizing any organic solvents.
- Shirini, Farhad,Daneshvar, Nader
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p. 110190 - 110205
(2016/11/30)
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- Amine-functionalized Metal-Organic Frameworks: An Efficient and Recyclable Heterogeneous Catalyst for the Knoevenagel Condensation Reaction
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A highly efficient and reusable catalyst based on metal-organic frameworks (MOF) has been synthesized by post-functionalization and applied in Knoevenagel condensations of various aldehydes and ketones. The catalytic efficiency was demonstrated by the hig
- Taher, Abu,Lee, Dong-Jin,Lee, Byoung-Ki,Lee, Ik-Mo
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supporting information
p. 1433 - 1437
(2016/06/01)
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- Betti base-modified magnetic nanoparticles as a novel basic nanocatalyst in Knoevenagel condensation and its related palladium nanocatalyst in Suzuki coupling reactions
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Betti base-modified Fe3O4 nanoparticles have been successfully designed and synthesized for the first time through the condensation of Fe3O4 magnetic nanoparticles coated by (3-aminopropyl)triethoxysilane with β
- Heidari, Payam,Cheraghali, Ramin,Veisi, Hojat
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p. 991 - 997
(2016/11/23)
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- Potassium fluoride/K10-montmorillonite nanostructure as a green and reusable catalyst under mild reaction conditions for the knovenagel condensation
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Potassium fluoride (KF)/montmorillonite (K10-MMT) nanostructure acts as an active heterogeneous base catalyst for Knovenagel condensation. Here we have described the catalytic activities of KF/K10 nanostructure in the condensation reaction of various subs
- Ghanei, Mercedeh,Khalilzadeh, Mohammad A.,Hashemi, Mohammad M.
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p. 665 - 669
(2016/05/09)
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- Fluorous bispidine: A bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water
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Fluorous bispidine-type ligands have been developed to facilitate its recovery and reusability and to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/Knoevenagel condensation in water under mild conditions. Application of the fluorous ligand was also extended to the surfactant-free copper-catalyzed allylic and benzylic sp3 C-H oxidation reaction in water. The fluorous ligands could be recovered using F-SPE with recovery ranging from 91-97% and could be reused five times with little loss of activity.
- Ang, Wei Jie,Chng, Yong Sheng,Lam, Yulin
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p. 81415 - 81428
(2015/10/06)
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- Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.
- Kiyani, Hamzeh,Ghorbani, Fatemeh
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p. 7847 - 7882
(2015/02/19)
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- 3-Aminopropyl-triethoxysilane Functionalized Graphene Oxide: A Highly Efficient and Recyclable Catalyst for Knoevenagel Condensation
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A solid base catalyst has been prepared by covalent functionalization of graphene oxide with 3-aminopropyl-triethoxysilane. The catalyst exhibits a superior catalytic performance in Knoevenagel condensation (over 90 % yield and at least seven times reusab
- Huang, Jie,Ding, Shunmin,Xiao, Weiming,Peng, Yadan,Deng, Shengjun,Zhang, Ning
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p. 1000 - 1007
(2015/09/01)
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- Ultrasound-promoted knoevenagel condensation catalyzed by KF-clinoptilolite
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Potassium fluoride-clinoptilolite, which is prepared from commercially available and cheap starting materials, was used as an efficient and recyclable catalyst for Knoevenagel condensation of aromatic aldehydes with active methylene compounds under ultras
- Keipour, Hoda,Hosseini, Abolfazl,Khalilzadeh, Mohammad A.,Ollevier, Thierry
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p. 645 - 650
(2015/11/09)
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