- Β-Cyclodextrin as a Biomimetic Catalyst for the Efficient Synthesis of 4-Oxo-pyrido[1,2-a] Pyrimidine-3-Carbonitrile in Aqueous Medium
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Abstract: Supramolecular β-cyclodextrin as a highly efficient, biodegradable, and reusable catalyst for the synthesis of 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonitrile derivatives (4a–s) is investigated via a cascade reaction of aldehydes, malanonitrile
- Ghorad, Akash,Mahalle, Sagar,Khillare, Lalit D.,Sangshetti, Jaiprakash N.,Bhosle, Manisha R.
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- Synthesis of novel spiro-oxazino-quinoline derivatives and study of their photophysical properties
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A convenient route was successfully developed for the synthesis of novel heterocycles such as spiro-oxazino-quinoline derivatives from 2-aminoquinoline-3-carbonitrile (4) in good yield. The Spiro-quinoline derivatives (6, 8 and 10) were synthesized and fu
- Rane, Bhupendra S.,Kazi, Muddassar A.,Bagul, Sandeep M.,Shelar, Deepak P.,Toche, Raghunath B.,Jachak, Madhukar N.
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- Tuning regioisomer reactivity in catalysis using bifunctional metal-organic frameworks with mixed linkers
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The activity of two bifunctional metal-organic frameworks (MOFs) with IRMOF-9 topology that contain amino, phosphine oxide and methyl groups is described. The amino group acts as an active site for the Knoevenagel condensation of ortho, meta or para nitro
- Xu, Xiaoying,Van Bokhoven, Jeroen A.,Ranocchiari, Marco
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- Successive oxidation-condensation reactions using a multifunctional gold-supported nanocomposite (Au/MgCe-HDO)
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The application of gold-supported nanocomposites is useful in clinical diagnostics because of their ability to provide bio-compatible and sensitive detection systems. A gold-supported magnesium hydroxide and cerium oxide nanocomposite framework (Au/MgCe-HDO) was synthesized and characterized via XRD, XPS, SEM, DLS, TEM, and TGA techniques. The nanocomposite was used as a selective catalyst for the aerobic oxidation of alcohols under mild reaction conditions followed by successive condensation reactions, like Knoevenagel and Claisen-Schmidt condensation. Substituted benzyl alcohols were converted into the corresponding carbonyl compounds in the presence of the Au/MgCe-HDO nanocomposite with O2 gas and toluene as a solvent. We observed that, upon the addition of malononitrile/ethyl cyanoacetate/acetophenone to the catalyst in the aerobic oxidation reaction, the reaction proceeds to produce the corresponding desired condensation product with up to 95% yield.
- Chandra, Ramesh,Kumar, Loveneesh,Kumar, Rupesh,Sehrawat, Hitesh,Tomar, Ravi,Verma, Nishant
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p. 3472 - 3481
(2022/02/21)
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- 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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- Engineering cellulose into water soluble poly(protic ionic liquid) electrolytes in the DBU/CO2/DMSO solvent system as an organocatalyst for the Knoevenagel condensation reaction
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The facile design and preparation of polyelectrolytes is a frontier topic in the fields of polymer science, energy storage devices and catalysis. Herein, linear water soluble cellulosic poly(protic ionic liquid) (CPIL) electrolytes were facilely and atom economically prepared after the dissolution of cellulose in the newly developed DBU/CO2/DMSO solvent system, followed by the simple addition of succinic anhydride under mild conditions. The DBU not only participated in the dissolution of cellulose as a solvent component, but also acted as an organocatalyst for the acylation reaction of cellulose with succinic anhydride, as well as a cation component in the targeted CPIL electrolytes. The reaction was optimized, and the effect of the reaction conditions on the chemical and physical properties of the CPILs was investigated. And then, as a proof of concept, the CPIL electrolyte aqueous solution was successfully used as the catalytic reaction media for the Knoevenagel condensation reaction. It was found that the reaction was homogeneous at the beginning, and the products could precipitate out from the media with the proceeding of the reaction, thus affording satisfactory filtration yields ranging from 56.7% to 93.8%. The solution properties of the CPIL aqueous solution were primarily investigated towards an in-depth understanding of the catalytic mechanism, by which a synergetic catalytic mechanism of the CPILs was proposed, and the reaction started with a nucleophilic addition reaction, and was then followed by a fast dehydration reaction. Finally, the direct reusability potential of the CPIL aqueous solution after the product filtration was also primarily investigated for the Knoevenagel condensation reaction.
- Shen, Yuqing,Yuan, Chaoping,Zhu, Xianyi,Chen, Qin,Lu, Shenjun,Xie, Haibo
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p. 9922 - 9934
(2021/12/24)
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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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- 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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- 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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- 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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- 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 0059-0060
(2020/07/02)
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- Enhanced catalytic activity of bio-fabricated ZnO NPs prepared by ultrasound-assisted route for the synthesis of tetraketone and benzylidenemalonitrile in hydrotropic aqueous medium
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Abstract: Mushroom-like mesoporous and hexagonal ZnO nanoparticles were synthesized from plant extract and chemical method respectively, by co-precipitation method in aqueous medium. Different morphological forms of ZnO NPs were characterized by XRD, TGA, FESEM, EDX, FTIR, UV–Vis and BET. Neem (Azadirachta indica) leaf extract and ultrasound irradiation have a crucial role in the formation of different morphologies of ZnO NPs. ZnO NPs synthesized from plant extract and hydrotrope show a synergistic effect that leads to efficient synthesis of benzylidenemalonitrile and tetraketone derivatives at room temperature in water. Simple preparation of the catalyst, excellent yields, reusability of catalyst with consistent activity and ease of product isolation are the most significant advantages of this green protocol. Graphic abstract: [Figure not available: see fulltext.]
- Attar, Suraj R.,Kamble, Santosh B.,Shinde, Bipin
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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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- 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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- A luminescent inorganic-organic hybrid, [Cd(C16H10N2O8S)(H2O)], for the selective and recyclable detection of chromates and dichromates in aqueous solution
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A new inorganic-organic hybrid compound [Cd(H2L)(H2O)], 1, {where, H2L2- = 4,4′-sulfonylbis(phenylene)bis(oxamate)} has been prepared under solvothermal conditions. The compound has a three-dimensional structure
- Kundu, Tanaya,Manna, Krishna,Jana, Ajay K.,Natarajan, Srinivasan
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p. 13263 - 13270
(2019/08/30)
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- Two Hg(II)-based Macrocycles Offering Hydrogen Bonding Cavities: Influence of Cavity Structure on Heterogeneous Catalysis
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We present synthesis and characterization of two Hg-macrocycles offering H-bonding based cavities of varying dimensions. Both Hg-macrocycles illustrate noteworthy difference in their catalytic performance that has been related to their cavity structures.
- Pachisia, Sanya,Gupta, Rajeev
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p. 6039 - 6047
(2019/10/21)
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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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- 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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- 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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- 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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- Rapid and efficient uncatalyzed knoevenagel condensations from binary mixture of ethanol and water
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This paper presents a new green protocol for Knoevenagel condensations of aldehydes and compounds with an active methylene group in a binary mixture of ethanol/water (3:7, v/v). This medium favored the uncatalyzed Knoevenagel reactions and easy workup pro
- Ferreira, Jo?o M. G. O.,De Resende Filho, Jo?o B. M.,Batista, Poliane K.,Teotonio, Ercules E. S.,Vale, Juliana A.
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p. 1382 - 1387
(2018/06/12)
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- 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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- 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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- Nitrogen enriched polytriazine as a metal-free heterogeneous catalyst for the Knoevenagel reaction under mild conditions
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A nitrogen enriched (52 wt%) nanoporous polytriazine with a high specific surface area up to 850 m2 g-1 was synthesized by an ultra-fast (30 min reaction time) microwave assisted route using the inexpensive precursors cyanuric chlori
- Chaudhary, Monika,Mohanty, Paritosh
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supporting information
p. 12924 - 12928
(2018/08/01)
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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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- 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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- Synthesis of Polyfunctionalized Pyrroles via Green Chemical Methods
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Water was found to be an excellent solvent for the one-pot synthesis of tetrasubstituted pyrrole derivatives under ultrasound involving the standard Knoevenagel condensation followed by the Michael type reaction. A new catalyst free system, excellent atom
- Pagadala, Ramakanth,Anugu, Sreenivasa
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p. 181 - 186
(2017/10/30)
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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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- Layered double hydroxide anchored ionic liquids as amphiphilic heterogeneous catalysts for the Knoevenagel condensation reaction
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In recent years, great attention has been dedicated to the development of heterogeneous base catalysts providing a green and sustainable process in benign aqueous media. Herein, the ionic liquid modified layered double hydroxide (LDH) based catalysts of L
- Li, Tengfei,Zhang, Wei,Chen, Wei,Miras, Haralampos N.,Song, Yu-Fei
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p. 3059 - 3067
(2018/03/06)
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- Polyoxoniobates as a superior Lewis base efficiently catalyzed Knoevenagel condensation
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The outstanding basicity of negative charged Lindqvist type Polyoxoniobate K7HNb6O19·13H2O (Nb6) have been proved experimentally as well as by theoretical NBO calculations, the results insights high electron density on terminal and bridging oxygen atoms of niobate anion. The most negative Natural Bond Orbital charge (NBO) of oxygen in Nb6 is ?1.001, which is a much more negative value than those reported in other polyoxometalates, that corroborates its high basicity thus likely to be employed as a strong base catalyst. Experimental study suggests that Nb6 can efficiently catalyze Knoevenagel condensation of various carbonyl compounds with active methylene compounds neglecting the steric and electronic effect of aromatic aldehydes under mild conditions. Kinetic test shows that Knoevenagel condensation of benzaldehyde with ethyl cyanoacetate exhibits second-order kinetics in the presence of Nb6 and the calculated activation energy is 43.3 kJ mol?1. Meanwhile, a proper mechanism according to the NBO study speculates that the most negative charged terminal oxygens in Nb6 would be pivotal in this transformation.
- Xu, Qiaofei,Niu, Yanjun,Wang, Guan,Li, Yingguang,Zhao, Yuan,Singh, Vikram,Niu, Jingyang,Wang, Jingping
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- The clean synthesis and confirmatory structural characterization of new 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano based on Kojic acid
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Abstract: A valuable and clean method was developed for the synthesis of the group of different novel 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles containing a 2-aminopyran moiety by using of azido kojic acid and various 2-arylidinemalononitriles in the presence of NH4Cl as a catalyst in a green solvent (ethanol) with excellent yields. All structures were analyzed by FT-IR, 1H, 13C NMR spectroscopy, and representatively, one compound was analyzed by X-ray crystallography technique. Crystallographic analyses indicated that of this compound a dimer formed via two weak intermolecular hydrogen bonds with d(N···O) distances of 2.927?? and made a 14-membered ring with centrosymmetric (Ci) form. Graphical abstract: [Figure not available: see fulltext.].
- Aghbash, Khadijeh Ojaghi,Pesyan, Nader Noroozi,Notash, Behrouz
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p. 2059 - 2067
(2018/09/14)
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- Knoevenagel Condensation of Aldehydes and Ketones with Malononitrile Catalyzed by Amine Compounds-Tethered Fe3O4@SiO2 Nanoparticles
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Abstract: A new magnetic nanoparticle supported-catalyst was developed for the Knoevenagel condensation between malononitrile and several aldehydes. The Fe3O4@SiO2-3N (where 3N = N1-(3-trimethoxysilylpropyl)diet
- de Resende Filho, Jo?o Batista M.,Pires, Gilvan P.,de Oliveira Ferreira, Jo?o Marcos Gomes,Teotonio, Ercules E. S.,Vale, Juliana A.
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p. 167 - 180
(2017/02/10)
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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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- 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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- 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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- 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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- Calcium ferrite, an efficient catalyst for knoevenagel condensation(A green approach)
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Calcium ferrite NPs catalyst have been used as a cheaper and highly efficient catalyst for Knoevenagel condensation of active methylene substrate with various carbonyl compounds affording condensed products in excellent yields in shorter reaction time. Th
- Pippal, Parveen,Singh, Prabal Pratap
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p. 1736 - 1743
(2017/10/27)
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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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- 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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- “On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids
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A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using “on water” concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086?M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method.
- Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Kashinath, Dhurke
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supporting information
p. 2865 - 2871
(2017/06/27)
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- Electrochemical approach for synthesis of 3-substituted indole derivatives
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An efficient and economical method was developed for synthesis of 3-substituted indole by using electrochemically induced condensation of various aldehyde, indole and malononitrile.
- Singh, Vinay K.,Dubey, Rahul,Upadhyay, Abhishek,Sharma, Laxmi Kant,Singh, Rana Krishna Pal
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supporting information
p. 4227 - 4231
(2017/10/12)
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- Glucose-coated superparamagnetic nanoparticle-catalysed pyrazole synthesis in water
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A green, benign, heterogeneous, superparamagnetic catalyst (Glu.@Fe3O4) was synthesized and characterized using Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy and vibrating sample magnetometry. The prepared catalyst was used to achieve a high-efficiency, low-cost, eco-friendly and easy-to-handle protocol for synthesizing substituted pyrazole derivatives from aldehydes, malononitrile and phenylhydrazine. The catalyst was also used in chromene synthesis. Glucose coated on magnetic nanoparticles provided excellent catalytic activity. The catalyst could be recycled for up to four runs without significant loss in catalytic activity.
- Esfandiary, Naghmeh,Nakisa, Athar,Azizi, Kobra,Azarnia, Jamshid,Radfar, Iman,Heydari, Akbar
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- Molecular modeling of drug-pathophysiological Mtb protein targets: Synthesis of some 2-thioxo-1, 3-thiazolidin-4-one derivatives as anti-tubercular agents
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Twenty novel 2-thioxo-1, 3-thiazolidin-4-one derivatives (5a-5t) were synthesized and evaluated for their antitubercular activity. The structure of the compounds was confirmed by IR, NMR and Mass Spectroscopy methods. In addition, single-crystal X-ray diffraction was performed for compound 5a. All the synthesized compounds were screened for their in-vitro antimycobacterial activity against MTB (H37RV, ATCC No: 27294) by Alamar Blue assay method. Compounds 5r, 5k, 5t displayed most potent in-vitro activity with MICs of 0.05, 0.1, 0.2 μg/ml concentrations respectively which are comparatively potent than the standards. Molecular docking and dynamics simulations were performed to find out the plausible mechanism of the titled compounds.
- Noorulla,Suresh, Ayyadurai Jerad,Devaraji, Vinod,Mathew, Bijo,Umesh, Devi
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p. 682 - 696
(2017/07/13)
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- Microporous polyurethane material for size selective heterogeneous catalysis of the Knoevenagel reaction
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The first polyurethane material which is microporous (BET surface area of 312 m2 g-1) is prepared by solvothermal synthesis and acts as highly efficient and recyclable heterogeneous catalyst in the Knoevenagel condensation showing si
- Dey, Sandeep Kumar,De Sousa Amadeu, Nader,Janiak, Christoph
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supporting information
p. 7834 - 7837
(2016/07/06)
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- Highly stable naphthalene core based novel cleft-shaped strain molecule: Influence of intermolecular H-bonding architectures
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The significance of intermolecular classical and non-classical H-bonding interactions in the stabilization of a naphthalene core based conformationally rigid cleft-shaped 1,5-dioxocin (BNAP) is presented here. The importance of H-bonding interactions to a
- Panja, Sumit Kumar,Dwivedi, Nidhi,Saha, Satyen
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p. 59574 - 59581
(2016/07/06)
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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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- 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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- 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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- Ni–Al2O3 as reusable heterogeneous catalyst for expedient one-pot synthesis of naphthopyrans
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Abstract: Ni–Al2O3 is an efficient and reusable heterogeneous catalyst for the synthesis of naphthopyrans by one-pot three-component reaction of naphthols, aldehydes, and malononitrile in EtOH/H2O (1:1) solvent medium. A c
- Kalita, Subarna Jyoti,Saikia, Nilakhy,Deka, Dibakar Chandra,Mecadon, Hormi
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p. 6863 - 6871
(2016/08/25)
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- Efficient preparation of Zr(IV)-salen grafted mesoporous MCM-41 catalyst for chemoselective oxidation of sulfides to sulfoxides and Knoevenagel condensation reactions
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Zr(IV)-salen-MCM-41 was prepared by reaction of NH2-MCM-41 with salicylaldehyde to afford Schiff base ligands. Thereafter, ZrOCl2·8H2O was reacted with the Schiff base ligands for complex formation. The structural properti
- Hajjami, Maryam,Ghorbani, Farshid,Rahimipanah, Sedighe,Roshani, Safoora
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p. 1852 - 1860
(2015/11/17)
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