- Controlling ZIF-8 nano- and microcrystal formation and reactivity through zinc salt variations
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We report here a simple method for controlling the crystal size and morphology of zeolitic imidazolate framework-8 (ZIF-8) nanocrystals in methanol solution. ZIF-8 crystals were prepared by mixing 2-methylimidazole (Hmim) with various zinc salts for 1 h a
- Schejn, Aleksandra,Balan, Lavinia,Falk, Veronique,Aranda, Lionel,Medjahdi, Ghouti,Schneider, Raphael
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Read Online
- Structure-induced Lewis-base Ga4B2O9 and its superior performance in Knoevenagel condensation reaction
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Solid Lewis-base catalysis is important in the production of fine chemicals. A Lewis-base Ga4B2O9 was synthesized by high temperature solid state reactions. It exhibited a high yield (90 %) and a high stability in Knoevena
- Cong, Rihong,Gao, Wenliang,Jiang, Pengfei,Wang, Duo,Yang, Tao,Yang, Yao
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Read Online
- Functionalization of A3B-type porphyrin with Fe3O4 MNPs. Supramolecular assemblies, gas sensor and catalytic applications
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The aim of this study was to synthesize different multifunctional materials containing 5-(4-carboxyphenyl)-5,10,15-tris(4-phenoxyphenyl)-porphyrin and iron oxide magnetic nanoparticles (MNPs). Besides, a new type of polymeric material comprising the same
- Mak, Carmen A.,Pericas, Miquel A.,Fagadar-Cosma, Eugenia
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Read Online
- Biguanide-functionalized hierarchical porous covalent organic frameworks for efficient catalysis of condensation reactions
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Covalent organic frameworks (COFs) can be rationally designed with desired physicochemical properties for a far-ranging application in catalytic systems. Herein, a biguanide-functionalized covalent organic framework was designed and prepared via N-alkylat
- Feng, Huiru,Gong, Kai,Li, Cunhao,Li, Haoran,Wang, Yunyun,Zhang, Daquan,Zhang, Huimin
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- 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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- 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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- 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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- Ferrocene-Functionalized Dithiocarbamate Zinc(II) Complexes as Efficient Bifunctional Catalysts for the One-Pot Synthesis of Chromene and Imidazopyrimidine Derivatives via Knoevenagel Condensation Reaction
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Four new mononuclear/coordination polymeric (CP) zinc(II) complexes (1-4) of ferrocenyl/pyridyl-functionalized dithiocarbamate ligands, N-ferrocenylmethyl-N-butyl dithiocarbamate (L1), N-ferrocenylmethyl-N-ethylmorpholine dithiocarbamate (L2), N-ferroceny
- Anamika,Drew, Michael G. B.,Kumar, Kamlesh,Singh, Nanhai,Yadav, Chote Lal
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p. 6446 - 6462
(2021/05/31)
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- Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds
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First copper(I) chalcogenones catalysed Knoevenagel Condensation reactions have been reported. No illustration of the utilization of this copper-chalcogenone complex class in Knoevenagel Condensation catalysis can be found. Thus, copper(I) bis(benzimidazole-2-chalcogenone) catalysts [Cu(L1)4]+BF4? (1) and [Cu(L2)4]+BF4? (2) (L1 = bis(1-isopropyl-benzimidazole-2-selone)-3-ethyl; L2 = bis(1-isopropyl-benzimidazole-2-thione)-3-ethyl) have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent catalytic activity has been depicted for various types of substrates with either electron-rich or deficient aryl aldehydes. The present investigation features relatively mild reaction conditions with good functional group tolerance and excellent yields. Graphic Abstract: The first copper(I)-chalcogenone complexes catalysed Knoevenagel Condensation reactions?have also been investigated, and revealed the best catalytic activities. [Figure not available: see fulltext.]
- Mannarsamy, Maruthupandi,Prabusankar, Ganesan
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- Attempts to access a series of pyrazoles lead to new hydrazones with antifungal potential against candida species including azole‐resistant strains
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The treatment of benzylidenemalononitriles with phenylhydrazines in refluxing ethanol did not provide pyrazole derivatives, but instead furnished hydrazones. The structure of hydra-zones was secured by X‐ray analysis. The chemical proof was also obtained by direct reaction of 3,4,5‐trimethoxybenzaldehyde with 2,4‐dichlorophenylhydrazine. Newly synthesized hydrazones were tested against eight Candida spp. strains in a dose response assay to determine the minimum inhibitory concentration (MIC99). Five compounds were identified as promising antifungal agents against Candida spp. (C. albicans SC5314, C. glabrata, C. tropicalis, C. parapsilosis and C. glabrata (R azoles)), with MIC99 values ranging from 16 to 32 μg/mL and selective antifungal activity over cy-totoxicity.
- B?cu, Elena,Dubar, Faustine,Ghinet, Alina,Kamus, Laure,Negru, Georgiana,Sendid, Boualem,Shova, Sergiu
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- A ru-complex tethered to a N-rich covalent triazine framework for tandem aerobic oxidation-knoevenagel condensation reactions
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Herein, a highly N-rich covalent triazine framework (CTF) is applied as support for a RuIII complex. The bipyridine sites within the CTF provide excellent anchoring points for the [Ru(acac)2(CH3CN)2]PF6 complex. The obtained robust RuIII@bipy-CTF material was applied for the selective tandem aerobic oxidation-Knoevenagel condensation reaction. The presented system shows a high catalytic performance (>80% conversion of alcohols to α, β-unsaturated nitriles) without the use of expensive noble metals. The bipy-CTF not only acts as the catalyst support but also provides the active sites for both aerobic oxidation and Knoevenagel condensation reactions. This work highlights a new perspective for the development of highly efficient and robust heterogeneous catalysts applying CTFs for cascade catalysis.
- Abednatanzi, Sara,Der Voort, Pascal Van,Derakhshandeh, Parviz Gohari,Leus, Karen,Schmidt, Johannes,Watson, Geert
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- Triazole-directed fabrication of polyoxovanadate-based metal-organic frameworks as efficient multifunctional heterogeneous catalysts for the Knoevenagel condensation and oxidation of alcohols
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By introducing 4-amino-1,2,4-triazole (4-NH2-trz), three new polyoxovanadate-based metal-organic frameworks (PMOFs) [Ni3(4-NH2-trz)6][V6O18]·3H2O (1), [Co3(4-NH2-trz)6][V6O18]·3H2O (2) and [Cu3OH(4-NH2-trz)3H2O][VO3]5·H2O (3) have been synthesized and thoroughly characterized by single-crystal X-ray diffraction (SXRD), powder X-ray diffraction (PXRD), infrared spectroscopy (FT-IR), thermogravimetric (TG) analysis and elemental analysis (EA). Among them, PMOFs1and2had similar structures containing [V6O18]6?clusters; however, PMOF3was isolated as a structure containing a [VO3]55?cluster when the amount of the 4-NH2-trz ligand was reduced to half with the other synthesis conditions being the same as those of PMOFs1and2except for the transition-metal chlorides. Furthermore, the negative charges of polyoxovanadate [V6O18]6?and [VO3]55?anions were balanced by trinuclear complex cations [Ni3(4-NH2-trz)6]6?for1, [Co3(4-NH2-trz)6]6?for2and [Cu3OH(4-NH2-trz)3H2O]5?for3, respectively. PMOFs1-3were further used as heterogeneous catalysts in the Knoevenagel condensation under solvent-free conditions and showed high catalytic activity. PMOF1showed moderate catalytic activities in the oxidation of various aromatic alcohols using H2O2as an oxidant. Moreover, PMOF1could be reused at least three times without losing its activity.
- Cheng, Xueli,Han, Yinfeng,Hu, Changwen,Huang, Xianqiang,Li, Jikun,Mei, Yu,Wei, Chuanping
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p. 10082 - 10091
(2021/08/03)
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- Nanochannel {InZn}-Organic Framework with a High Catalytic Performance on CO2Chemical Fixation and Deacetalization-Knoevenagel Condensation
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The rare combination of InIII 5p and ZnII 3d in the presence of a structure-oriented TDP6- ligand led to a robust hybrid material of {(Me2NH2)[InZn(TDP)(OH2)]·4DMF·4H2O}n (NUC-42) with the interlaced hierarchical nanochannels (hexagonal and cylindrical) shaped by six rows of undocumented [InZn(CO2)6(OH2)] clusters, which represented the first 5p-3d nanochannel-based heterometallic metal-organic framework. With respect to the multifarious symbiotic Lewis acid-base and Br?nsted acid sites in the high porous framework, the catalytic performance of activated NUC-42a upon CO2 cycloaddition with styrene oxide was evaluated under solvent-free conditions with 1 atm of CO2 pressure, which exhibited that the reaction could be well completed at ambient temperature within 48 h or at 60 °C within 4 h with high yield and selectivity. Moreover, because of the acidic function of metal sites and a central free pyridine in the TDP6- ligand, deacetalization-Knoevenagel condensation of acetals and malononitrile could be efficiently facilitated by an activated sample of NUC-42a under lukewarm conditions.
- Chen, Hongtai,Zhang, Zhengguo,Hu, Tuoping,Zhang, Xiutang
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p. 16429 - 16438
(2021/11/01)
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- 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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- 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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- Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
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Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
- Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
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- Introduction of 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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- An Ionic Liquid on a Porous Organic Framework Support: A Recyclable Catalyst for the Knoevenagel Condensation in an Aqueous System
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Porous aromatic frameworks (PAFs) that feature a high density of phenyl rings in their robust frameworks are attractive platforms for catalysis because of their extremely high stability, high surface area, and adjustable pore size. In this paper, two PAF-
- Chen, Peng,Sun, Jin-Shi,Wu, Xian-Tao,Xiao, En-Kai,Zhang, Lei,Zhu, Guangshan
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p. 943 - 947
(2020/06/01)
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- A new type IV DES: a competent green catalyst and solvent for the synthesis of α,β-unsaturated diketones and dicyano compounds by Knoevenagel condensation reaction
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DESs are new and greener alternatives to ionic liquids formed by mixing components that are capable of forming hydrogen bonds between them. The strong hydrogen bond interactions between the constituents make a large depression in the melting points compared to pure constituents. They are emerging as green solvents and have loomed as adorable alternatives to conventional organic solvents and ionic liquids with unique properties. In the present article, four new CeCl3·7H2O-based DESs were developed and their physical properties were studied. Their activities were checked in the Knoevenagel condensation reaction of dimedone/malononitrile with various aldehydes. The recyclability of the catalyst/solvent was achieved up to five runs without much change in the activity.
- Shaibuna,Hiba,Theresa, Letcy V.,Sreekumar
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p. 14723 - 14732
(2020/09/21)
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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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- 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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- Tandem Condensation-Hydrogenation to Produce Alkylated Nitriles Using Bifunctional Catalysts: Platinum Nanoparticles Supported on MOF-Derived Carbon
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Tandem catalysis, which allows multiple steps of a reaction to take place without the need for separation and purification, is highly desired for the design of efficient and environmentally-friendly chemical processes. Herein, the pyrolysis of UiO-66-NHs
- Huang, Ao,Nie, Renfeng,Zhang, Biying,Pei, Yuchen,Chen, Minda,Behera, Ranjan,Yu, Jiaqi,Luan, Xuechen,Hunter, Nicholas T.,Ke, Ming,Huang, Wenyu
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p. 602 - 608
(2019/12/27)
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- Highly Active Bisamino Functionalized Zr(IV)-UiO-67 Metal-Organic Framework for Cascade Catalysis
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This work reports the synthesis and characterization of Zr(IV)-based UiO-67-(NH2)2 (called 1) metal-organic framework. Activated 1 (named 1') was shown to be an efficient tandem catalyst in the conversion of benzaldehydedimethyl acet
- Das, Aniruddha,Anbu, Nagaraj,Mostakim,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
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supporting information
p. 2830 - 2834
(2020/07/04)
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- Synthesis and catalytic activities of a Zn(ii) based metallomacrocycle and a metal-organic framework towards one-pot deacetalization-Knoevenagel tandem reactions under different strategies: A comparative study
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Solvothermal reactions between a pyridine based amide functionalized dicarboxylic acid, 4,4′-{(pyridine-2,6-dicarbonyl)bis(azanediyl)}dibenzoic acid (H2L), and zinc(ii) nitrate in the absence and presence of a base produced the binuclear metallomacrocyclic compound [Zn2(L)2(H2O)4]·2(H2O)·6(DMF) (1) and the metallomacrocyclic based two dimensional MOF [Zn5(L)4(OH)2(H2O)4]n·8n(DMF)·4n(H2O) (2), respectively. Compound 1 bears two tetrahedral Zn(ii) centres, whereas the 2D framework 2 includes a penta-nuclear Zn(ii) cluster as a secondary building block unit, with two of the metal cations assuming a tetrahedral type geometry and the remaining three an octahedral type geometry. The topological analyses reveal that compound 1 has a 2-connected uninodal net and framework 2 has a 2, 8-connected binodal net. These compounds heterogeneously catalyse the tandem deacetalization-Knoevenagel condensation reactions carried out under conventional heating, microwave irradiation or ultrasonic irradiation. Comparative studies show that ultrasonic irradiation (final product yield of 99percent after 2 h of reaction time) provides the most favourable method (e.g., microwave irradiation leads to a final product yield of 91percent after 3 h of reaction time). Moreover, the catalysts can be reused at least for five consecutive cycles without losing activity significantly.
- Guedes Da Silva, M. Fátima C.,Karmakar, Anirban,Pombeiro, Armando J. L.,Rúbio, Guilherme M. D. M.,Soliman, Mohamed M. A.
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p. 8075 - 8085
(2020/07/10)
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- Cascade reaction synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof
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The invention discloses a cascade reaction synthesis method of 2-(phenylmethylene)malononitrile or a derivative thereof. According to the invention, a dendritic acid-alkali catalyst based on cross-linked polystyrene is synthesized, and 2-(phenylmethylene) malononitrile or a derivative thereof is synthesized in batches by successfully applying a cascade reaction into fluid chemistry, so that the method of the invention has advantages of substantially reduced, yield increase and no separation process of a catalyst and a product compared with the traditional test tube reaction.
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Paragraph 0073-0077
(2020/03/12)
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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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- 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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- 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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- 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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- 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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supporting information
p. 3795 - 3800
(2019/03/05)
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- Heterogeneous basic catalyst and continuous flow preparing method for alpha, beta-unsaturated compound based on heterogeneous basic catalyst
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The invention discloses a preparing method for a heterogeneous basic catalyst. The preparing method includes the steps that chlorine balls, a nitrogen-containing compound and a solvent are put into areaction container, pH is adjusted, and the mixture reac
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Paragraph 0075-0079
(2019/07/16)
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- Design and Construction of a Chiral Cd(II)-MOF from Achiral Precursors: Synthesis, Crystal Structure and Catalytic Activity toward C-C and C-N Bond Forming Reactions
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Using achiral components, a V-shaped dicarboxylic acid (H2L) and a conformationally flexible bidentate linker (bpp), a thermally stable chiral metal organic framework {[Cd(bpp)(L)(H2O)]·DMF}n (1), where H2L = 4,
- Gupta, Vijay,Mandal, Sanjay K.
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p. 3219 - 3226
(2019/03/28)
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- Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes
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A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 molpercent PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
- Mangaonkar, Saeesh R.,Singh, Fateh V.
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p. 4473 - 4486
(2019/11/21)
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- Synthesis and anticholinesterase activity of novel non-hepatotoxic naphthyridine-11-amine derivatives
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Abstract: In the present study, 14 novel naphthyridine-11-amine derivatives were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 12-(4-Fluorophenyl)-1,2,3,4,7,8,9,10-octahydrodibenz
- Zengin Kurt, Belma
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p. 625 - 638
(2018/12/11)
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- Tandem synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof
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A tandem synthesis method of 2-(phenylmethylene)malononitrile or a derivative thereof is disclosed. The general structural formula of the 2-(phenylmethylene)malononitrile or a derivative thereof is shown in the description, wherein R1 is hydrogen, p-methoxy, 2-bromo, 3-bromo or 4-bromo, and R2 is a cyano or ester group. A chloromethylated polystyrene microsphere acid-base functionalized catalyst is synthesized, a tandem reaction is successfully applied to the flow chemistry, and the 2-(phenylmethylene)malononitrile or a derivative thereof is synthesized in a gram scale. Compared with traditional test tube reactions, the method greatly reduces the reaction time, improves the yield and product purity, and avoids a step of separating a product from the catalyst.
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Paragraph 0069-0073
(2019/10/01)
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- New Bifunctional Metal-Organic Frameworks and Their Utilization in One-Pot Tandem Catalytic Reactions
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Two new metal-organic framework (MOF) compounds were synthesized by a room temperature slow diffusion reaction. The compounds, [Cd3(C8H3SO7)2(C10H8N4)3(C3H7NO)2](C3H7NO)2·(CH3OH)4, I, and [Cd3(C8H3SO7)2(C12H10N4)3(C3H7NO)2](C12H10N4)·(C3H7NO)2, II, have comparable structures formed by Cd-sulfoisopthalate layers cross-linked by bipyridyl linkers forming three-dimensional structures. The compounds have both Lewis acidic (Cd metal centers) as well as basic (azine, free pyridine, and uncoordinated sulfo oxygens) sites, and they exhibited good catalytic activity for one-pot tandem deacetalization-Knoevenagel condensation reactions. The compounds exhibit catalytic activity both in the presence of a solvent as well as in solvent-free conditions. Compound I also exhibits good proton conductivity at room temperature.
- Mistry, Subhradeep,Sarkar, Anupam,Natarajan, Srinivasan
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p. 747 - 755
(2019/01/11)
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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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- Ordered mesoporous Γ-Al2O3 as highly efficient and recyclable catalyst for the Knoevenagel reaction at room temperature
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Coumarins are important class of organic compounds and intensively used in agricultural and pharmaceutical industries. We have developed a strategy for the synthesis of coumarin derivatives quantitatively via Knoevenagel condensation reaction of an ortho-hydroxyaryl aldehyde and an activated methylene compounds in the presence of ordered mesoporous γ-Al2O3 as a heterogeneous catalyst. The catalyst has been thoroughly characterized through powder X-ray diffraction, N2 sorption analysis, FTIR spectroscopy, TG/DTA, NH3-TPD and CO2-TPD (temperature programmed desorption) analysis. The material possesses periodicity in mesopores and both surface acidic and basic sites having strengths of 1.47 and 1.11 mmol g?1, respectively, which is highly favorable for carrying out the Knoevenagel condensation reaction for the synthesis of a wide range of condensation product (yields ～98%) under very mild conditions. This amphoteric catalyst exhibits good surface Lewis acidity/basicity and high recyclability up to sixth reaction cycles without any significant loss in the product yield.
- Bhanja, Piyali,Kayal, Utpal,Bhaumik, Asim
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p. 220 - 227
(2018/04/05)
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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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- Construction of two Zn(ii)/Cd(ii) multifunctional coordination polymers with mixed ligands for catalytic and sensing properties
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With the purpose of exploring the catalytic and sensing properties of crystalline materials, two coordination polymers were rationally constructed by the reactions of Zn(ii)/Cd(ii) ions with methyl-3-hydroxy-5-carboxy-2-thiophenecarboxylate (H2
- Xue, Li-Ping,Li, Zhao-Hao,Zhang, Ting,Cui, Jia-Jia,Gao, Yue,Yao, Jia-Xin
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p. 14203 - 14209
(2018/08/28)
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- TEDETA@BNPs as a basic and metal free nanocatalyst for Knoevenagel condensation and Hantzsch reaction
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In this work, Boehmite nanoparticles (BNPs) were synthesized in water using commercially available materials and further N,N,N′,N′-tetraethyldiethylentriamin (TEDETA) was supported on the surface of BNPs, and used as organo-basic catalyst in four-componen
- Ghorbani-Choghamarani, Arash,Heidarnezhad, Zahra,Tahmasbi, Bahman,Azadi, Gouhar
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p. 2281 - 2293
(2018/08/28)
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- Sulfuric acid heterogenized on magnetic Fe3O4 nanoparticles: A new and efficient magnetically reusable catalyst for condensation reactions
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Immobilized sulfuric acid on magnetic Fe3O4 nanoparticles (Fe3O4 MNPs-OSO3H) as a new solid acid nanocomposite was successfully synthesized and its catalytic activity in a series of condensation reactions was studied. High catalytic activity, simple separation from reaction mixture by an external magnet and good reusability are several eco-friendly advantages of this catalytic system. It is noteworthy that this catalytic system is applicable to a wide range of spectrum of aromatic aldehydes, and the desired products were obtained in good to excellent yields under mild conditions. The use of ecofriendly solvents makes also this synthetic protocol ideal and fascinating from the environmental point of view.
- Shiri, Lotfi,Zarei, Setare,Kazemi, Mosstafa,Sheikh, Davood
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- 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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- 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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- 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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- 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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- 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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- Ultrasound-assisted rapid synthesis of β-cyanoepoxides using hypervalent iodine reagents
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An elegant approach for the rapid synthesis of β-cyanoepoxides 3 by the epoxidation of β-cyanostyrenes 1 with PIDA 2a is described. The epoxidation of β-cyanostyrenes 1 was performed with 1.2 equiv. of PIDA 2a in MeCN-H2O (1:1) at room temperature in ultrasonic bath. The epoxidation reactions were completed in short reaction time and β-cyanoepoxides 3 were isolated in 69–94% yields.
- Singh, Fateh V.,Mangaonkar, Saeesh R.,Kole, Priyanka B.
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supporting information
p. 2169 - 2176
(2018/07/21)
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