- Modulating the basicity of Zn-MOF-74: Via cation exchange with calcium ions
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The fine-tuning of metal-based molecular building blocks in Zn-MOF-74 through post-synthetic cation exchange with Ca2+ significantly enhances its basicity and corresponding catalytic performance. The resulting material, exemplified by Ca/Zn-MOF-74, is sho
- Zhang, Zhuxiu,Xiao, Yue,Cui, Mifen,Tang, Jihai,Fei, Zhaoyang,Liu, Qing,Chen, Xian,Qiao, Xu
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- Knoevenagel condensation in aqueous micellar media using EDAHS as a new Bronsted acidic ionic liquid
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The Knoevenagel condensation between aromatic aldehydes and malononitrile, barbituric acid or 1,3-dimethylbarbituric acid with ethane-1,2-diammonium hydrogen sulfate (EDAHS) in aqueous micellar media, using sodium dodecyl sulfate is described. EDAHS was found to be a highly active and stable Bronsted acidic ionic liquid catalyst under the reaction conditions. Graphical Abstract: [Figure not available: see fulltext.].
- Bahrami, Kiumars,Khodaei, Mohammad M.,Babajani, Nasrin,Naali, Fardin
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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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- 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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- 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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- A Cationic Zinc-Organic Framework with Lewis Acidic and Basic Bifunctional Sites as an Efficient Solvent-Free Catalyst: CO2 Fixation and Knoevenagel Condensation Reaction
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A novel two-dimensional cationic framework [Zn2(TCA)(BIB)2.5]·(NO3) (1) (H3TCA = tricarboxytriphenyl amine, BIB = 1,3-bis(imidazol-1-ylmethyl)benzene) was successfully achieved. Compound 1 not only presents a mo
- Yao, Cheng,Zhou, Shaolin,Kang, Xiaojing,Zhao, Yang,Yan, Rui,Zhang, Yan,Wen, Lili
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- An efficient and environment friendly procedure for the synthesis of arylmethylenemalononitrile catalyzed by strong base anion-exchange resin in water
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Knoevenagel condensation of malononitrile with aromatic aldehydes catalyzed by strong base anion-exchange resin in water results aryl- methylenemalononitrile in 74-98% yield at room temperature.
- Jin, Tong-Shou,Zhang, Jian-She,Wang, Ai-Qing,Li, Tong-Shuang
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- An efficient method for knoevenagel condensation catalyzed by tetrabutylammonium hexatungstate [TBA]2[W6O19] as novel and reusable heterogeneous catalyst
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Tetrabutylammonium hexatungstate [TBA]2[W6O 19] has been efficiently used as catalyst for the synthesis of electrophilic alkenes via the Knoevenagel condensation reaction of aromatic aldehydes with malononitrile. The catal
- Davoodnia, Abolghasem
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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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- Fast method for synthesis of ylidenemalononitriles
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Ylidenemalononitrile can be prepared from aromatic aldehydes and malononitrile by grinding at room temperature, catalyzed by potassium carbonate under solvent-free conditions. Copyright Taylor & Francis Group, LLC.
- Zhang, Ming,Zhang, Ai-Qin,Chen, Huan-Huan,Chen, Jun,Chen, Hai-Yan
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- Synthesis and characterization of Al2O3-SiO2-MgO nanocomposite prepared by sol-gel process as an efficient catalyst for the Knoevenagel condensation of aldehydes with malononitrile
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Abstract The composite of Al2O3-SiO2 and Al2O3-SiO2-MgO nanocomposite were synthesized by sol-gel method and FT-IR, XRD, FE-SEM, EDAX, TEM, and BET surface area analysis were used to charac
- Mobarakeh, Mahmood Iranpour,Saffar-Teluri, Ali,Tabrizi, S. A. Hassanzadeh
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- The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile by grinding in the absence of solvents and catalysts
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An improved Knoevenagel condensation reaction of aldehydes and malononitrile can be achieved by grinding at room temperature in the absence of solvents and catalysts. This process is simple, efficient, economical, and environmentally benign. Compared to r
- Ren, Zhongjiao,Cao, Weigud,Tong, Weiqi
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- 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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- A readily accessible porous organic polymer facilitates high-yielding Knoevenagel condensation at room temperature both in water and under solvent-free mechanochemical conditions
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A novel nitrogen-rich amorphous porous organic polymer has been synthesized using a microwave-assisted process. Its high chemical stability, reusability and poor solubility enable the use of the porous polymer as a metal-free heterogeneous catalyst for C–
- Sarma, Parishmita,Sarmah, Kashyap Kumar,Kakoti, Dharittri,Mahanta, Sanjeev Pran,Adassooriya, Nadeesh Madusanka,Nandi, Goutam,Das, Pranab Jyoti,Bu?ar, Dejan-Kre?imir,Thakuria, Ranjit
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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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- Highly active zinc oxide-supported lithium oxide catalyst for solvent-free Knoevenagel condensation
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Li2O/ZnO catalyst was prepared by wet impregnation method and characterized by XRD, SEM, EDX, FTIR, BET surface area and UV-Vis diffuse reflectance spectroscopy. This study revealed a decrease in average particle size and change in the shape of
- Basude, Manohar,Bhongiri, Yadagiri,Masula, Keshavulu,Pasala, Vijay Kumar,Puppala, Veerasomaiah,Sunkara, Prasad
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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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- Cu-metal-organic framework supported on chitosan for efficient condensation of aromatic aldehydes and malononitrile
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In this study, a novel copper-based metal-organic framework (Cu-MOF)-immobilized modified chitosan (CS-CA), CS-CA/Cu-MOF, has been constructed easily and applied as an extremely efficient and economic mesoporous catalyst for the Knoevenagel condensation between aromatic aldehydes with malononitrile under mild reaction conditions. The resultant catalyst is characterized via various techniques including FTIR, XRD, FE-SEM, EDX, TEM, BET and STA analyses. The CS-CA/Cu-MOF was reused eight times without a noteworthy decrease in the catalytic activity. The use of CS-CA/Cu-MOF results in outstanding catalytic activity, high recyclability, very short reaction time at 25 °C, and an easy work-up process for the Knoevenagel condensation.
- Yousefian, Mahnaz,Rafiee, Zahra
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- Cellulose stabilized Fe3O4 and carboxylate-imidazole and Co-based MOF growth as an exceptional catalyst for the Knoevenagel reaction
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In this study, Fe3O4 nanoparticles were functionalized with cellulose, and then hybridized with cobalt (II)-based metal-organic framework (Co-MOF) containing carboxylate and imidazole functionalities. FTIR, XRD, FE-SEM, TEM, BET, EDX
- Zare, Elham,Rafiee, Zahra
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- Amine-functionalized hollow mesoporous nano-bowl with bulky acid-imprinted free space around base sites and DMF-annealed mesoporous channels as an efficient solid base catalyst
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Tailoring free spaces around catalytic sites and constructing inter-connected channels between them are highly attractive for achieving easy accessibility of reactants to catalytic sites. In this study, a strategy for constructing free space around base s
- Li, Shan,Ma, Xuebing,Wei, Shuai,Zhang, Jianing,Zhang, Li
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- Hydroquinone and benzoquinone-catalyzed aqueous Knoevenagel condensation
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A Knoevenagel condensation of various aldehydes with malononitrile effectively proceeded in the presence of hydroquinone/benzoquinone mixed catalysts at room temperature in H2O. Furthermore, γ-deuterium-labeled α,β-unsaturated nitrile derivatives were als
- Koyama, Kaho,Kuwata, Marina,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya,Yamada, Tsuyoshi
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supporting information
p. 6594 - 6597
(2020/09/21)
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- Application of GO/COF as a novel, efficient and recoverable catalyst in the Knoevenagel reaction
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Hybrid composite based on graphene oxide (GO) and covalent organic framework (COF) [GO/COF] was developed via a simple solvothermal method, at which GO was applied as a platform to load COF based on melamine and terephthaldehyde. The synthesized hybrid na
- Monehzadeh, Fatemeh,Rafiee, Zahra
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- Organocatalytic Cascade Knoevenagel–Michael Addition Reactions: Direct Synthesis of Polysubstituted 2-Amino-4H-Chromene Derivatives
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Abstract: In this report, we documented novel strategy for the synthesis of bioactive polysubstituted 2-amino-4H-chromine derivatives under a heterogeneous Al-MCM-41-LDH@APTES (ALAM) catalysis. A synthetic procedure is developed to prepare Al-MCM-41-LDH@APTES (ALAM) heterogeneous basic catalysts. Mesoporous Al-MCM-41 is functionalized by known grafting chemistry via layered double hydroxide (LDH) nanosheets and (3-aminopropyl)triethoxysilane (APTES) moiety as a basic organocatalyst. The resulting catalysts contain amino group functionality on the external surface as well as inside the layers and the basicity can be tuned by the loading of APTES. The samples were fully characterized by 29Si and 13C CP/MAS NMR, infrared absorption spectroscopy, TEM, XPS, EDX, TGA, XRD, CO2-TPD, N2 adsorption isotherms measurements, and they were successfully examined for the cascade type Knoevenagel–Michael addition reactions. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The present catalytic method is simple and robust for diversity oriented synthesis which proceeds good to excellent yields without generating any hazards waste. The broad substrate scope, excellent functional group compatibility makes this protocol highly useful towards synthesis of polysubstituted α-cyanoacrylates, α-cyanoacrylonitriles and 2-amino-4H-chromenes with an electron-donating or electron-withdrawing group. We have also successfully established a flow reaction system, gram-scale synthesis as well as catalyst recyclability up to six catalytic cycles without appreciable loss of its activity. Graphic Abstract: [Figure not available: see fulltext.].
- Jadhav, Sanjay N.,Patil, Seema P.,Sahoo, Dipti Prava,Rath, Dharitri,Parida, Kulamani,Rode, Chandrashekhar V.
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p. 2331 - 2351
(2020/02/25)
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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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- 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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- Mercaptopyridine resorcinol calix [4] arene zinc complex as well as preparation method and application thereof
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The invention discloses a mercaptopyridine resorcinol calix [4] arene zinc complex and a preparation method thereof. The chemical formula of the complex is [Zn2(m-bdc)2(L)],8DMF.2CH3OH, wherein DMF represents N, N-dimethyl formamide. The preparation method comprises steps as follows: 0.04 mmol of Zn(NO3)2.6H2O with weight of 0.012 g, 0.04 mmol of isophthalic acid with weight of 0.007 g and 0.10 mmol of a ligand L with weight of 0.012 g are added to a reaction kettle, 5 mL of DMF and 3 mL of methanol are taken as reaction solvents, and all components are heated for 3 days at the temperature of100 DEG C. The complex has a layered structure and is high in synthetic repeatability and stable in product performance; as a heterogeneous catalyst, the complex has high catalytic efficiency; the complex can selectively detect Cr2O7 anions and Fe metal cations.
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Paragraph 0016; 0017
(2019/05/08)
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- Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)
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Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.
- Rupanawar, Bapurao D.,Veetil, Sruthi M.,Suryavanshi, Gurunath
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p. 6232 - 6239
(2019/11/05)
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- Synthesis of multifunctional polymer containing Ni-Pd NPs via thiol-ene reaction for one-pot cascade reactions
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Recently, acid–base bifunctional catalysts have been considered due to their abilities, such as the simultaneous activation of electrophilic and nucleophilic species and their high importance in organic syntheses. However, the synthesis of acid–base catalysts is problematic due to the neutralization of acidic and basic groups. This work reports a facial approach to solve this problem via the synthesis of a novel bifunctional polymer using inexpensive materials and easy methods. In this way, at the first step, heterogeneous poly (styrene sulfonic acid-n-vinylimidazole) containing pentaerythritol tetra-(3-mercaptopropionate) (PETMP) and trimethylolpropane trimethacrylate (TMPTMA) cross-linkers were synthesized in the pores of a mesoporous silica structure using click reaction as a novel bifunctional acid–base catalyst. After that, Ni-Pd nanoparticles supported on poly (styrenesulfonic acid-n-vinylimidazole)/KIT-6 as a novel trifunctional heterogeneous acid–base-metal catalyst was prepared. The prepared catalysts were characterized by various techniques like FT-IR, TGA, ICP-AES, DRS-UV, TEM, FE-SEM, EDS-Mapping, and XRD. The synthesized catalysts were efficiently used as bifunctional/trifunctional catalysts for one-pot, deacetalization-Knoevenagel condensation and one-pot, three-step and a sequential reaction containing deacetalization-Knoevenagel condensation-reduction reaction. It is important to note that the synthesized catalyst showing high chemo-selectivity for the reduction of nitro group, alkenyl double bond and ester group in the presence of nitrile. Moreover, it was found that the different nanoparticles including Ni, Pd, and alloyed Ni-Pd showing different chemo-selectivity and catalytic activity in the reaction.
- Javad Kalbasi, Roozbeh,Mesgarsaravi, Niloofar,Gharibi, Reza
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- Co2+ immobilized on highly ordered mesoporous graphitic carbon nitride (ompg-C3N4/Co2+) as an efficient and recyclable heterogeneous catalyst for one-pot tandem selective photo-oxidation/Knoevenagel condensation
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Design and synthesis of efficient heterogeneous photocatalysts is an important task for practical applications due to the increasing environmental challenges and energy crisis. In this work, Co2+ modified highly ordered mesoporous graphitic carbon nitride (ompg-C3N4/Co2+) was prepared through a simple procedure involving sonication treatment. The obtained catalyst was characterized using FT-IR, XRD, ICP-OES, FE-SEM, UV–vis DRS, N2 adsorption-desorption, and TGA. It was found that the ompg-C3N4/Co2+ can function as a multifunctional heterogeneous photocatalyst for the one-pot tandem selective photo-oxidation/ Knoevenagel condensation. More interestingly, the obtained ompg-C3N4/Co2+ represented a high photocatalytic activity in benzyl alcohol oxidation without any oxidant under air atmosphere and visible light irradiation.
- Ghafuri, Hossein,Jafari, Ghazaleh,Rashidizadeh, Afsaneh,Manteghi, Faranak
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- Calix[4]arene-based polyoxometalate organic-inorganic hybrid and coordination polymer as heterogeneous catalysts for azide-alkyne cycloaddition and Knoevenagel condensation reaction
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Based on a neutral pyridyl-functional calix[4]arene ligand (L = tetrakis [(3-pyridylmethyl)oxy]-p-tertbutylcalix[4]arene), one polyoxometalate-based organic-inorganic hybrid [Cu2L(SiW12O40)0.5]·CH3CN·
- Yue, Liu-Juan,Liu, Ying-Ying,Xu, Guo-Hai,Ma, Jian-Fang
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p. 15871 - 15878
(2019/10/22)
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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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- 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 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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- Cadmium Naphthalenedisulfonate Complex as Heterogeneous Catalyst in the Knoevenagel Condensation
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The reaction of naphthalene-1,5-disulfonate (1,5-nds), 2,4,5-tris(pyridin-4-yl)imidazole (tpim), and cadmium(II) acetate dihydrate Cd(OAc)2·2H2O afforded a 2D coordination polymer, [Cd(tpim)(1,5-nds)]n (1). Crystal structu
- Deng,Guo,He,Ji
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p. 117 - 121
(2019/04/13)
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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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- 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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- 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 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 0061-0064
(2018/09/08)
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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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- 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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- 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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- 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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- Binary copper and iron oxides immobilized on silica-layered magnetite as a new reusable heterogeneous nanostructure catalyst for the Knoevenagel condensation in water
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Abstract: In this study, a novel heterogeneous and reusable nanostructure catalyst was synthesized through the immobilization of bimetallic Cu–Fe mixed oxides on silica-layered magnetite. The prepared nanomagnetic Fe3O4@SiO2/su
- Gilanizadeh, Masumeh,Zeynizadeh, Behzad
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p. 6053 - 6070
(2018/05/26)
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- Synthesis and characterization of the immobilized Ni-Zn-Fe layered double hydroxide (LDH) on silica-coated magnetite as a mesoporous and magnetically reusable catalyst for the preparation of benzylidenemalononitriles and bisdimedones (tetraketones) under
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Herein, novel magnetic Fe3O4@SiO2@Ni-Zn-Fe layered double hydroxide (LDH) intercalated with water molecules and carbonate anions as interlayer contents was prepared as a new heterogeneous and separable nanocatalyst. The me
- Gilanizadeh, Masumeh,Zeynizadeh, Behzad
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p. 8553 - 8566
(2018/06/08)
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- Nmp-based ionic liquids: Recyclable catalysts for both hetero-Michael addition and Knoevenagel condensation in water
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A series of novel N-methyl piperidine (Nmp)-based ionic liquids with 1,2-propanediol group are synthesized and used as catalysts for both hetero-Michael addition of α,β-unsaturated amides and Knoevenagel condensation at room temperature in water; and all the examined substrates could be transformed into corresponding products in good to excellent yields. Meanwhile IL-catalyzed hetero-Michael addition of α,β-unsaturated amides in water has not been reported in the previous literatures. Additionally, the catalyst is recyclable for the two reactions. This finding provides a green catalyst for both hetero-Michael addition of α,β-unsaturated amides and Knoevenagel condensation in water.
- Yang, Pengkun,Liu, Yawei,Chai, Ling,Lai, Zhenzhen,Fang, Xiaomin,Liu, Baoying,Zhang, Wenkai,Lu, Minghua,Xu, Yuanqing,Xu, Hao
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supporting information
p. 1060 - 1067
(2018/05/23)
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- Synthesis and characterization of bromine source immobilized on diethylenetriamine-functionalized magnetic nanoparticles: A novel, versatile and highly efficient reusable catalyst for organic synthesis
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Bromine source immobilized on magnetic nanoparticles functionalized with diethylenetriamine was successfully synthesized and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, vibrating sample magnetometry, thermogravimetric analysis and X-ray diffraction. The catalytic activity in the synthesis of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives and in Knoevenagel condensation was studied. The bromine catalyst can be magnetically recovered and reused several times without significant loss of its catalytic activity. All products were obtained in high to excellent yields.
- Shiri, Lotfi,Rahmati, Sadegh,Ramezani Nejad, Zahra,Kazemi, Mosstafa
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- Fe3O4–cysteamine hydrochloride magnetic nanoparticles: New, efficient and recoverable nanocatalyst for Knoevenagel condensation reaction
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Fe3O4 magnetic nanoparticles (MNPs) were obtained using a reduction–precipitation method. These MNPs were modified with cysteamine hydrochloride. This catalyst was characterized using a number of physicochemical measurements. The Fe
- Maleki, Razieh,Kolvari, Eskandar,Salehi, Mehdi,Koukabi, Nadiya
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- 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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- 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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- 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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- Ultrasound promoted synthesis of arylmethylenemalonitriles catalyzed by melamine
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Arylmethylenemalonitriles were synthesized in the presence of melamine through the Knoevenagel condensation of aldehydes with malononitrile in ethanol. Two strategies such as the conventional stirring and ultrasound-assisted method were performed in this
- Liu, Qing,Ai, Hong Mei
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p. 565 - 569
(2016/08/26)
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- Organic-inorganic hybrid polyoxometalate and its graphene oxide-Fe3O4 nanocomposite, synthesis, characterization and their applications as nanocatalysts for the Knoevenagel condensation and the synthesis of 2,3-dihydroquinazolin-4(1: H)-ones
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The simple and high yield synthesis of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O (PPD = p-phenylenediamine) as a new organic-inorganic hybrid polyoxometalate is reported. The new compound consists of trimetal-substitution polyoxometalate of A-β-SiW9Cu3O3710-, water molecules and coordinated and noncoordinated PPD molecules. H6Cu2[PPD]6[SiW9Cu3O37]·12H2O was firmly grafted on graphene oxide decorated with Fe3O4 nanoparticles. These nanocomposites were characterized by elemental analyses, thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), X-ray photoelectron spectrum (XPS), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), and alternating gradient force magnetometer (AGFM). The results indicate that the size range of the nanoparticles are between 20 and 60 nm. The catalytic activity of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O and the magnetically reusable nanocomposite of GO@Fe3O4@H6Cu2[PPD]6[SiW9Cu3O37]·12H2O were investigated in the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
- Khoshnavazi, Roushan,Bahrami, Leila,Havasi, Forugh
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p. 100962 - 100975
(2016/11/09)
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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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- 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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