- Preparation of a Pickering emulsion by modification of an amine-functionalized graphene oxide surface with organosilane: Efficient catalyst for the Knoevenagel condensation of malononitrile with aldehydes at mild temperature
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In this study, a series of Pickering emulsions for catalysis of Knoevenagel condensations of malononitrile with aldehydes were prepared by surface modification of amine-functionalized graphene oxide (GO-NH2) with trimethoxymethylsilane (MTMS).
- Qian, Bingxu,Wang, Fei,Li, Dongsheng,Li, Yongxin,Zhang, Bo,Zhu, Jie
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Read Online
- Synthesis, structure, and catalytic properties of a copper(II) coordination polymer material constructed from 5-nitro-1,2,3-benzenetricarboxylic acid and bis(4-pyridylformyl)piperazine mixed ligands
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One three-dimensional coordination polymer material, {[Cu3(nbta)2(bpfp)2(H2O)2](H2O)2}n (H3nbta = 5-nitro-1,2,3-benzenetricarboxylic acid, bpfp = bis(4-pyri
- Li, Zhao-Hao,Xue, Li-Ping,Qin, Qiu-Pei,Zhao, Yi-Jing
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- Unexpected polymorphism during a catalyzed mechanochemical Knoevenagel condensation
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The transformation of a base-catalyzed, mechano-assisted Knoevenagel condensation of mono-fluorinated benzaldehyde derivatives (p-, m-, o-benzaldehyde) with malonodinitrile was investigated in situ and in real time. Upon milling, the para-substituted prod
- Haferkamp, Sebastian,Paul, Andrea,Michalchuk, Adam A. L.,Emmerling, Franziska
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- Amine Functionalized Graphene Oxide Stabilized Pickering Emulsion for Highly Efficient Knoevenagel Condensation in Aqueous Medium
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Abstract: A Pickering emulsion catalytic system was developed using amphiphilic amine-functionalized graphene oxide (GO-NH2) for a Knoevenagel condensation in aqueous medium instead of organic solvent. The properties of GO-NH2 and th
- Zhu, Jie,Wang, Fei,Li, Dongsheng,Zhai, Jie,Liu, Ping,Zhang, Weihong,Li, Yongxin
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Read Online
- New Pyrano-4H-benzo[g]chromene-5,10-diones with Antiparasitic and Antioxidant Activities
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New pyranonaphthoquinone derivatives were synthesized and investigated for their activity against Trypanosoma brucei, Leishmania major, and Toxoplasma gondii parasites. The pentafluorophenyl derivative was efficacious against T. brucei with single digit m
- Al Nasr, Ibrahim S.,Jentzsch, Jana,Shaikh, Amin,Singh Shuveksh, Priti,Koko, Waleed S.,Khan, Tariq A.,Ahmed, Khursheed,Schobert, Rainer,Ersfeld, Klaus,Biersack, Bernhard
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- Phosphine-Catalyzed (4 + 2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives
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The δ-sulfonamido-substituted enones were employed as phosphine acceptor in phosphine-catalyzed (4 + 2) annulation of 1,1-dicyanoalkenes. They served as a four-membered synthon to react with 1,1-dicyanoalkenes under mild reaction conditions, producing pip
- Liu, Min,Zhou, Leijie,Shi, Wangyu,Hu, Yimin,Liao, Jianning,Duan, Zeqing,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
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supporting information
p. 7703 - 7707
(2021/10/20)
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- Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations
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Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.
- Kazia, Armands,Melngaile, Renate,Mishnev, Anatoly,Veliks, Janis
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supporting information
p. 1384 - 1388
(2020/03/03)
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- Manganese-organic framework assembled by 5-((4′-(tetrazol-5″-yl)benzyl)oxy)isophthalic acid: A solvent-free catalyst for the formation of carbon–carbon bond
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A new three-dimensional manganese-based metal–organic framework Mn4L2(HL)(H2O)5, (1), based on semi-rigid 5-((4′-(tetrazol-5′’-yl)benzyl)oxy)isophthalic acid ligand (H3L) have been prepared and charac
- Jiang, Yansong,Xu, Jianing,Zhu, Ziqian,Jiang, Changwei,Ma, Lin,Wang, Hui,Wang, Li,Fan, Yong
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- Synthesis, in vitro and in silico screening of 2-amino-4-aryl-6-(phenylthio) pyridine-3,5-dicarbonitriles as novel α-glucosidase inhibitors
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Inhibition of α-glucosidase enzyme is of prime importance for the treatment of diabetes mellitus (DM). Apart of many organic scaffolds, pyridine based compounds have previously been reported for wide range of bioactivities. The current study reports a series of pyridine based synthetic analogues for their α-glucosidase inhibitory potential assessed by in vitro, kinetics and in silico studies. For this purpose, 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles 1–28 were synthesized and subjected to in vitro screening. Several analogs, including 1–3, 7, 9, 11–14, and 16 showed many folds increased inhibitory potential in comparison to the standard acarbose (IC50 = 750 ± 10 μM). Interestingly, compound 7 (IC50 = 55.6 ± 0.3 μM) exhibited thirteen-folds greater inhibition strength than the standard acarbose. Kinetic studies on most potent molecule 7 revealed a competitive type inhibitory mechanism. In silico studies have been performed to examine the binding mode of ligand (compound 7) with the active site residues of α-glucosidase enzyme.
- Ali, Muhammad,Faramarzi, Mohammad Ali,Jabbar, Abdul,Khan, Khalid Mohammed,Larijani, Bagher,Mahdavi, Mohammad,Perveen, Shahnaz,Salar, Uzma,Shamim, Shahbaz,Taha, Muhammad
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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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- 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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- Stereoselective one-pot synthesis of polycyanosubstituted piperidines
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Abstract: An effective and facile multicomponent method for the synthesis of polysubstituted piperidines is described. The Michael–Mannich type cascade of benzylidenemalononitriles with aromatic aldehydes and ammonium acetate or aqueous ammonia provides c
- Vereshchagin, Anatoly N.,Karpenko, Kirill A.,Elinson, Michail N.,Gorbunov, Sergey V.,Gordeeva, Alexandra M.,Proshin, Pavel I.,Goloveshkin, Alexander S.,Egorov, Mikhail P.
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p. 1979 - 1989
(2018/09/21)
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- H3PW12O40/mpg-C3N4 as an efficient and reusable bifunctional catalyst in one-pot oxidation-Knoevenagel condensation tandem reaction
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A single-site bifunctional catalyst for the oxidation-Knoevenagel condensation tandem reaction was prepared by the immobilization of phosphotungstic acid (HPW) on mesoporous graphitic carbon nitride (mpg-C3N4) via electrostatic interaction (HPW/mpg-C3N4). The results of Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), solid-state 31P nuclear magnetic resonance (solid-state 31P NMR), zeta potentials, X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) demonstrated that HPW was successfully immobilized on the protonated mpg-C3N4 by electrostatic interaction. The acid amounts of the catalysts were determined by NH3 temperature programmed desorption (NH3-TPD). The textural properties and morphology of HPW/mpg-C3N4 were characterized by N2 adsorption-desorption, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). 30% HPW/mpg-C3N4 shows the best catalytic performance in the tandem reaction with 98.4% benzyl alcohol conversion and 96.2% selectivity to benzylidene malononitrile. The excellent catalytic performance of 30% HPW/mpg-C3N4 in the tandem reaction is due to the good catalytic performance of HPW in the oxidation and Knoevenagel condensation, respectively. Furthermore, protonated mpg-C3N4 not only acts as a support to facilitate good dispersion of HPW but also promotes the Knoevenagel condensation reaction effectively. Moreover, the HPW/mpg-C3N4 catalyst could be recycled easily without significant loss of catalytic activity.
- Wang, Hefang,Wang, Cunyue,Yang, Yongfang,Zhao, Meng,Wang, Yanji
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p. 405 - 417
(2017/08/14)
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- Zirconium-mediated multicomponent reactions of 1,3-butadiynes with ylidenemalononitriles to form functionalized 1,8-naphthyridine and cyclopenta[b]pyridine derivatives
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Zirconocene-mediated multicomponent reactions of 1,3-butadiynes with ylidenemalononitriles in the absence or presence of CuCl have been developed. In the absence of CuCl, 1,3-butadiyne couples with three molecules of ylidenemalononitriles to yield azazirconacycles bearing a hexahydro-1,8-naphthyridine skeleton with high stereoselectivity. In the presence of CuCl, cyclopenta[b]-pyridine or cyclopenta[ b ]quinolin-1-one derivatives are obtained via transmetalation of Zr-C bond to Cu-C bond as the key reaction step. These domino-type reactions proceed with high chemo-, regio- and/or stereoselectivities, and allowing the formation of multiple C-N and C-C bonds in a single operation.
- Yu, Shasha,Sun, Renhong,Chen, Haoyi,Xie, Xin,Liu, Yuanhong
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supporting information
p. 1420 - 1424
(2015/01/30)
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- A general post-synthetic modification approach of amino-tagged metal-organic frameworks to access efficient catalysts for the Knoevenagel condensation reaction
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In this manuscript, four common transition-metal derived metal-organic frameworks have been extensively investigated as heterogeneous catalyst supports for Knoevenagel condensation reactions. A simple post-synthetic modification strategy was employed for the rapid and facile introduction of a primary alkyl amino group. The resulting novel MOF-RNH2 catalysts showed greatly enhanced Knoevenagel condensation reactivities towards a variety of aldehyde electrophiles. IRMOF-3 proved to be an unsuitable heterogeneous catalyst support due to its fragile nature upon treatment with bases. The novel zirconium based UiO-66-NH-RNH2 and chromium based Cr-MIL-101-NH-RNH2 materials showed excellent catalytic reactivities, while being highly convenient to synthesize. The basic catalytic activity was further extended to the Henry reaction, and excellent catalytic reactivity was achieved. The size-selectivity was also studied to show that the Knoevenagel condensation occurred inside of the porous structure of the MOF catalyst. The recycling properties of zirconium, aluminum and chromium derived MOFs were evaluated and zirconium based UiO-66 and chromium based Cr-MIL-101 showed excellent catalytic efficiency after five reaction cycles.
- Luan, Yi,Qi, Yue,Gao, Hongyi,Andriamitantsoa, Radoelizo S.,Zheng, Nannan,Wang, Ge
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supporting information
p. 17320 - 17331
(2015/08/24)
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- Ultrasound-promoted an efficient method for one-pot synthesis of 2-amino-4,6-diphenylnicotinonitriles in water: A rapid procedure without catalyst
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A green and convenient approach to the synthesis of 2-amino-4,6- diphenylnicotinonitriles via four-component reaction of malononitrile, aromatic aldehydes, acetophenone derivatives and ammonium acetate in water under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this sonocatalyzed procedure.
- Safari, Javad,Banitaba, Sayed Hossein,Khalili, Shiva Dehghan
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experimental part
p. 1061 - 1069
(2012/07/03)
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- Design and an efficient synthesis of natural product-based cyclopenta[b]pyran derivatives with potential bioactivity
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A series of 4-aryl-cyclopenta[b]pyran derivatives, designed based on natural product scaffold, were synthesized efficiently via multi-component reaction under solvent-free and catalyst-free conditions. This chemistry provides a new compound library with potential activity for biomedical screening.
- Yao, Changsheng,Jiang, Bei,Li, Tuanjie,Qin, Bingbin,Feng, Xiaodong,Zhang, Honghong,Wang, Cuihua,Tu, Shujiang
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supporting information; experimental part
p. 599 - 601
(2011/02/27)
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- The synthesis of some derivatives based on the 4-Benzyl-1H-Pyrazole-3,5- Diamine core
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The three-step synthesis of 4-benzyl-1H-pyrazole-3,5-diamines 2 from commercially available aldehydes 3 is given. The Knoevenagel condensation was utilized to assemble the initial carbon framework, resulting in the benzylidenemalononitriles 4 which were d
- Jedinak, Lukas,Krystof, Vladimir,Cankara, Petr
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experimental part
p. 371 - 383
(2011/04/15)
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- A NHC-Involved, cascade, metal-free, and three-component synthesis of 2,3-diarylated fully substituted furans under solvent-free conditions
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An efficient synthesis of 2,3-diarylated fully substituted furans was performed through the sequential reactions of Knoevenagel reaction, Stetter reaction catalyzed by NHC, and intramolecular cyclization under solvent-free conditions. The protocol has the
- Yu, Chenxia,Lu, Jun,Li, Tuanjie,Wang, Donglin,Qin, Binbin,Zhang, Honghong,Yao, Changsheng
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supporting information; experimental part
p. 2420 - 2424
(2011/11/05)
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- (DIARYL-METHYL)-MALONONITRILES AND THEIR USE AS ESTROGEN RECEPTOR LIGANDS
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The present invention concerns compounds of formula (I) where R1, R2, R3 and R4 are defined in the specification.
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Page/Page column 15-16
(2010/02/15)
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- A novel eco-friendly process for the synthesis of 2- chlorobenzylidenemalononitrile and its analogues using water as a solvent
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A simple and novel eco-friendly process for the synthesis of 2-chlorobenzylidene malononitrile (CS) and their analogues in water using 1-methyl imidazole (catalyst) has been developed. The reaction conditions for the preparation of CS are optimized for la
- Pande, Ambuja,Ganesan, Kumaran,Jain, Asheesh Kumar,Gupta, Pradeep Kumar,Malhotra, Ramesh Chandra
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p. 133 - 136
(2012/12/24)
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- Medicine comprising dicyanopyridine derivative
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Compounds having a high conductance-type of calcium-activated K channel opening effect and a smooth muscle relaxant effect for bladder based on the K-channel opening effect, which can be used in treating pollakiuria and urinary incontinence, are provided.
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