- Highly active zinc oxide-supported lithium oxide catalyst for solvent-free Knoevenagel condensation
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Li2O/ZnO catalyst was prepared by wet impregnation method and characterized by XRD, SEM, EDX, FTIR, BET surface area and UV-Vis diffuse reflectance spectroscopy. This study revealed a decrease in average particle size and change in the shape of
- Basude, Manohar,Bhongiri, Yadagiri,Masula, Keshavulu,Pasala, Vijay Kumar,Puppala, Veerasomaiah,Sunkara, Prasad
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- New mononuclear and binuclear cu(Ii), co(ii), ni(ii), and zn(ii) thiosemicarbazone complexes with potential biological activity: Antimicrobial and molecular docking study
-
Herein, we report the synthesis of eight new mononuclear and binuclear Co2+, Ni2+, Cu2+, and Zn2+ methoxy thiosemicarbazone (MTSC) complexes aiming at obtaining thiosemicarbazone complex with potent biological a
- Gaber, Ahmed,Refat, Moamen S.,Belal, Arafa A.M.,El-Deen, Ibrahim M.,Hassan, Nader,Zakaria, Rozan,Alhomrani, Majid,Alamri, Abdulhakeem S.,Alsanie, Walaa F.,Saied, Essa M.
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- MOFs assembled from C 3symmetric ligands: Structure, iodine capture and role as bifunctional catalysts towards the oxidation-Knoevenagel cascade reaction
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Three new NiII/CoII-metal organic frameworks were self-assembled by the reaction of C3 symmetric 1,3,5-tribenzoic acid (H3BTC) and 2,4,6-tris(4-pyridyl)-1,3,5-triazine (4-TPT) ligands and NiII/CoII salts under solvothermal conditions. Isomorphous MOF1 and MOF2 exhibit a 3D pillar-layer framework based on binuclear M2(OH)(COO)2 units connected by tritopic BTC3- and 4-TPT ligands with a novel (3,5)-connected topology net. MOF3 displays a 3-fold interpenetrated 3D network exhibiting a (3,4)-connected topology net. The porous MOF3 can reversibly take up I2. The activated MOFs contain both Lewis acid (NiII center) and basic (uncoordinated pyridyl or carboxylic groups) sites, and act as bifunctional acid-base catalysts. The catalytic measurements demonstrate that the activated MOF3 exhibits good activities for benzyl alcohol oxidation and the Knoevenagel reaction and can be recycled and reused for at least four cycles without losing its structural integrity and high catalytic activity. Thus, the catalytic properties for the oxidation-Knoevenagel cascade reaction have also been studied.
- Zhang, Ying-Ying,Liu, Qing,Zhang, Lin-Yan,Bao, Yu-Mei,Tan, Jing-Yi,Zhang, Na,Zhang, Jian-Yong,Liu, Zhen-Jiang
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p. 647 - 659
(2021/01/28)
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- Ammonium chloride: An efficient and environmentally benign catalyst for knoevenagel condensation of carbonyl and active methylene compounds
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In the present study, a rapid, simple and an efficient procedure for the Knoevenagel condensation of various carbonyl and active methylene compounds in ethanol at a moderate temperature in the presence of a catalytic amount of an efficient, environmentall
- Tasqeeruddin,Asiri, Yahya I.,Mujahid Alam
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p. 3024 - 3028
(2021/01/06)
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- Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate: Via aza-Michael-Michael addition
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A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation
- Chen, Chinpiao,Lee, Gene-Hsian,Palanimuthu, Arunan
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p. 13591 - 13600
(2020/04/23)
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- A Simple and Highly Versatile Procedure for the Knoevenagel Condensation Promoted by an Efficient, Eco-Friendly, and Recyclable nano-ZnO Catalyst
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Abstract: A simple, highly versatile, and efficient protocol for the synthesis of substituted olefins from various aromatic aldehydes and active methylene compounds by Knoevenagel condensation using an efficient, eco-friendly, and recyclable nano-ZnO cata
- Alam, M. M.,Asiri, Ya. I.,Sulthana, S. Sh.,Tasqeeruddin, S.
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p. 315 - 321
(2020/04/17)
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- Highly efficient FeNP-embedded hybrid bifunctional reduced graphene oxide for Knoevenagel condensation with active methylene compounds
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We have synthesized atypical highly active bifunctional FeNPs implanted on amino-modified reduced graphene oxide (FeNPs/Am@rGO) [where FeNPs = Fe nanoparticles; Am = Primary aromatic amine derivatives such as p-phenylenediamine (PPD) and/or aniline (AN)]
- Patel, Dikin,Vithalani, Ravi,Modi, Chetan K.
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p. 2868 - 2881
(2020/03/03)
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- Overcoming acid–base copolymer neutralization using mesoporous carbon and its catalytic activity in the tandem deacetalization–Knoevenagel condensation reaction
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Abstract: Acid–base copolymer materials are of considerable interest because of their fundamental implications for acid–base bifunctional catalysis applications. However, quenching the acid and base sites of the copolymer with each other in free radical polymerizations is still challenging. Herein, we demonstrate that the polymerization of styrenesulfonic acid-co-4-vinylpyridine into the mesoporous carbon material (i.e., CMK-3) can control the chain growth polymerization and result in decreasing the interaction of the acid–base sites. The results showed that by using CMK-3, 40% of the acid and base sites of the copolymer remain in their original form while 60% of acid and base sites convert to the pyridinium and sulfonate forms. Furthermore, it is demonstrated that this material can be processed as a heterogeneous bifunctional acid–base catalyst in the tandem one-pot acid–base reaction (i.e., deacetalization–Knoevenagel condensation reaction) with a high catalytic activity in aqueous media. Graphic abstract: [Figure not available: see fulltext.].
- Javad Kalbasi, Roozbeh,Rahmati, Fatemeh,Mazaheri, Omid
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p. 3413 - 3430
(2020/05/16)
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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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- 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
- -
-
Paragraph 0090-0094
(2019/07/16)
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- Imine-bridged periodic mesoporous organosilica as stable high-activity catalytic for Knoevenagel reaction in aqueous medium
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An imine-functionalized mesoporous solid base catalyst (BA@BE-PMO) was prepared by template agent-directed self-assembly condensation of bis[3-(triethoxysilyl)propyl]amine and 1,2-bis(triethoxysilyl)ethane in acid solution. The imine groups with catalytic
- Sun, Zechun,Wang, Yiran,Zhang, Zhiruo,Zhu, Fengxia,Zhao, Pusu,Li, Guisheng,Shao, Fengfeng,Rui, Jiahui
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p. 3107 - 3121
(2019/03/13)
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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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- Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions
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A series of new prolinamide polyacrylonitrile fiber catalysts with tunable length of alkyl linker and different linker group were prepared by covalent bonding for the first time and well characterized by mechanical strength, FT-IR, XRD, EA, TGA, SEM and water contact angel. The catalytic activities of these fiber catalysts were evaluated in Knoevenagel condensation and one-pot Knoevenagel-Michael multicomponent tandem reactions to synthesize α, β-unsaturated nitrile and 2-amino-4H-chromene derivatives in water. The result show that the suitable linker length attaching amines to fiber matrix as well as the constructed hydrophobic microenvironment by linker group within the surface layers of fiber materials effectively promotes the reactions. In addition, the good swollen capacity of fiber in solvent ensure that the reaction proceed well. Fiber catalyst PANPA?2F modified by prolinamide with a C2 alkyl chain exhibited the best catalytic performance and can be easily recovered and reused for at least ten consecutive cycles without significant loss of catalytic activity and active sites leaching.
- Zhu, Hai,Xu, Gang,Du, Huimin,Zhang, Chenlu,Ma, Ning,Zhang, Wenqin
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p. 217 - 229
(2019/05/16)
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- Molecular Pivot-Hinge Installation to Evolve Topology in Rare-Earth Metal–Organic Frameworks
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Linker desymmetrization has been witnessed as a powerful design strategy for the discovery of highly connected metal–organic frameworks (MOFs) with unprecedented topologies. Herein, we introduce molecular pivot-hinge installation as a linker desymmetrization strategy to evolve the topology of highly connected rare-earth (RE) MOFs, where a pivot group is placed in the center of a linker similar to a hinge. By tuning the composition of pivot groups and steric hindrances of the substituents on various linker rotamers, MOFs with various topologies can be obtained. The combination of L-SO2 with C2v symmetry and 12-connected RE9 clusters leads to the formation of a fascinating (4,12)-c dfs new topology. Interestingly, when replacing L-SO2 with a tetrahedra linker L-O, the stacking behaviors of RE-organic layers switch from an eclipsed mode to a staggered stacking mode, leading to the discovery of an intriguing hjz topology. Additionally, the combination of the RE cluster and a linker [(L-(CH3)6)] with more bulky groups gives rise to a flu topology with a new 8-c inorganic cluster. The diversity of these RE-MOFs was further enhanced through post-synthetic installation of linkers with various functional groups. Functionalization of each linker with acidic and basic units in the mesoporous RE-based PCN-905-SO2 allows for efficient cascade catalytic transformation within the functionalized channels.
- Feng, Liang,Wang, Yutong,Zhang, Kai,Wang, Kun-Yu,Fan, Weidong,Wang, Xiaokang,Powell, Joshua A.,Guo, Bingbing,Dai, Fangna,Zhang, Liangliang,Wang, Rongming,Sun, Daofeng,Zhou, Hong-Cai
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supporting information
p. 16682 - 16690
(2019/11/11)
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- Amino- and sulfo-bifunctionalized hyper-crosslinked organic nanotube frameworks as efficient catalysts for one-pot cascade reactions
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In this paper, novel amino- and sulfo-bifunctionalized hyper-crosslinked organic nanotube frameworks (H-ONTFs) were directly prepared by templating core-shell bottlebrush copolymers via a Friedel-Crafts (F-C) alkylation reaction, in which the acidic sites were anchored into the wall of nanotubes and basic sites were introduced onto the inner layer wall of nanotubes through a rational molecular design strategy. The resulting acid-base bifunctionalized H-ONTFs showed excellent catalytic activities for one-pot deacetalization-Knoevenagel cascade reactions due to their open-ended structure, large surface area and good multi-porosity interconnectivity.
- Meng, Guojie,Gao, Shengguang,Liu, Ying,Zhang, Li,Song, Chunmei,Huang, Kun
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supporting information
p. 2269 - 2273
(2019/02/05)
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- Efficient Synthesis of Branched Polyamine Based Thermally Stable Heterogeneous Catalyst for Knoevenagel Condensation at Room Temperature
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Abstract: In this paper, a new convenient strategy for the synthesis of polyethylenimine functionalized Si-MCM-41 grafted on surface modified graphene oxide has been developed. The as-synthesised catalyst exerts good catalytic activity and reusability tow
- Chaudhuri, Haribandhu,Gupta, Radha,Dash, Subhajit
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p. 1703 - 1713
(2018/04/02)
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- Development of Amine Functionalized Wrinkled Silica Nanospheres and Their Application as Efficient and Recyclable Solid Base Catalyst
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Abstract: Amine functionalized wrinkled silica nanospheres (WSiO2–NH2) were successfully synthesized by using a simple biphase sol–gel approach. The prepared silica nanospheres were characterized by using various techniques, such as
- Shabir, Javaid,Garkoti, Charu,Surabhi,Sah, Digvijay,Mozumdar, Subho
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p. 194 - 204
(2017/11/20)
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- DABCO-catalyzed Knoevenagel condensation of aldehydes with ethyl cyanoacetate using hydroxy ionic liquid as a promoter
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N-(2-Hydroxy-ethyl)-pyridinium chloride ([HyEtPy]Cl) was synthesized and explored as a novel promoter for 1,4-diazabicyclo [2.2.2] octane (DABCO)-catalyzed Knoevenagel condensation reactions, which showed better catalytic activity compared to other ionic liquid (IL) that had no hydroxyl group attached to the IL scaffold. The effect of hydrogen bond formation between the hydroxyl group of [HyEtPy]Cl and the carbonyl group of aldehyde played an important role in the Knoevenagel condensation reaction. In the [HyEtPy]Cl-H2O-DABCO composite system, Knoevenagel condensation reactions proceeded smoothly and cleanly, and the corresponding Knoevenagel condensation products were obtained in good to excellent yields in all cases examined. This protocol provides a versatile solvent-catalyst system, which has notable advantages such as being eco-friendly, ease of work-up and convenient reuse of the ionic liquid.
- Meng, Dan,Qiao, Yongsheng,Wang, Xin,Wen, Wei,Zhao, Sanhu
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p. 30180 - 30185
(2018/09/11)
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- l-Lysine Functionalized Polyacrylonitrile Fiber: A Green and Efficient Catalyst for Knoevenagel Condensation in Water
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Abstract: The l-lysine functionalized polyacrylonitrile fiber (PANLF) was prepared by grafting the l-lysine into a commercially available polyacrylonitrile fiber and showed highly catalytic activity for Knoevenagel condensation reaction. With low temperature (45?°C) and short reaction time (1?h), the fiber catalyst was well applicable to Knoevenagel condensation of a wide range of aldehydes and the yields could reach up to 99%. Interestingly, only in water could the reaction take place smoothly (with a yield of 88%) and a polar micro-environment promoted reaction process had been proposed to explain this phenomenon. Besides, the fiber catalyst has advantages of easy preparation, high functional degree, strong mechanical strength and thermal stability, etc. And it can be reused at least 5 times without further treatment and performed well in scaled-up experiment (amplified 50 times) and flow chemistry experiment (no loss of catalytic activity after 48?h), which indicates its potential application in industry application. Graphical Abstract: [Figure not available: see fulltext.].
- Li, Pengyu,Liu, Yuanyuan,Ma, Ning,Zhang, Wenqin
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p. 813 - 823
(2018/01/27)
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- Hierarchically Pore Structure poly 2-(Dimethyl amino) ethyl methacrylate/Hi-ZSM-5: A Novel Acid–Base Bi-functional Catalyst as Heterogeneous Platform for a Tandem Reaction
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Abstract: A simple method is developed to prepare an efficient and low cost acid–base bifunctional catalyst by using poly 2-(dimethyl amino) ethyl methacrylate as a basic part and hierarchical ZSM-5 as an acidic part of the catalyst. Tandem reaction of deacetalization–Knoevenagel condensation was selected to evaluate the prepared catalyst and the outcomes were excellent. Graphical Abstract: [Figure not available: see fulltext.].
- Javad Kalbasi, Roozbeh,Khojastegi, Anahita
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p. 958 - 971
(2018/02/12)
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- Direct synthesis and application of bridged diamino-functionalized periodic mesoporous organosilicas with high nitrogen contents
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Bridged diamino-functionalized periodic mesoporous organosilicas [BD-PMO(Et), Et = ethyl] materials were synthesized directly by co-condensation of 2-bis (triethoxysilyl)ethane (BTEE) and 1,4-bis[3-(tirmethoxysilyl)-propyl]ethylenediamino (BTMSEN) under acidic conditions with pluronic triblock copolymer P123 as a template. The nitrogen content in BD-PMO(Et) could be adjusted up to 40% without disturbing the ordered mesoporous structure. These materials were proved to be effective heterogeneous catalysts for the liquid-phase reactions such as Knoevenagel and Henry condensations as well as in the intermolecular cross-double-Michael addition reaction between α-methyl-β-nitrostyrene and α, β-unsaturated ketone. They exhibited comparable catalytic activities with homogeneous catalyst piperazine and can be reused for several times without any negative environmental impact.
- Zhu, Feng-Xia,Zhao, Pu-Su,Sun, Xiao-Jun,An, Li-Tao,Deng, Yong,Wu, Jia-Min
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- Mn-MOF@Pi composite: synthesis, characterisation and an efficient catalyst for the Knoevenagel condensation reaction
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We have synthesised new Mn-MOF@Pi composite by encapsulation of piperidine in desolvated Mn-MOF and investigated its catalytic performance in Knoevenagel condensation reaction. The newly developed composite is compatible with various aromatic aldehydes an
- Rambabu, Darsi,Ashraf, Mohammad,Pooja,Gupta, Ankush,Dhir, Abhimanew
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supporting information
p. 4691 - 4694
(2017/11/17)
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- 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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- 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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- PhI(OAc)2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives
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A phenyliododiacetate (PhI(OAc)2) mediated an efficient and novel protocol for the Knoevenagel reaction has been successfully accomplished. A base free, simple and straightforward method afforded wide substrate scope and good functional group tolerance, having high yields (80–92%) under environmentally benign and mild reaction conditions.
- Khan, Danish,Mukhtar, Sayeed,Alsharif, Meshari A.,Alahmdi, Mohammed Issa,Ahmed, Naseem
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supporting information
p. 3183 - 3187
(2017/07/18)
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- Synthesis and structural investigation of 2-aminomethyl-3-(4-methoxy-phenyl)-propionic acid containing a peptide analogue of the amyloidogenic AS(6-7) sequence: Inhibition of fibril formation
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The incorporation of a single β-amino acid moiety in a highly amyloidogenic peptide sequence resulted in the complete inhibition of amyloid fibril formation. The Boc-l-Phe-l-Leu-OMe sequence 1, which has sequence identity with the N-terminal AS(6-7) of th
- Paikar, Arpita,Debnath, Mintu,Podder, Debasish,Sasmal, Supriya,Haldar, Debasish
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supporting information
p. 4218 - 4225
(2017/07/10)
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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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- Amine-functionalized ionic liquid-based mesoporous organosilica as a highly efficient nanocatalyst for the Knoevenagel condensation
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A novel amine-functionalized ionic liquid-based periodic mesoporous organosilica (PMO-IL-NH2) was prepared and characterized and its catalytic performance was investigated in the Knoevenagel reaction. PMO-IL-NH2 was prepared by simul
- Elhamifar, Dawood,Kazempoor, Somayeh,Karimi, Babak
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p. 4318 - 4326
(2016/07/06)
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- Synthesis and characterization of ionic liquid based bifunctional periodic mesoporous organosilica supported potassium carbonate as very efficient nanocatalyst for the Knoevenagel condensation
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A novel ionic liquid based bifunctional periodic mesoporous organosilica supported potassium carbonate (BPMO-IL-KCO3) is prepared, characterized and its catalytic efficiency is studied in the Knoevenagel reaction. The BPMO-IL-KCO3 wa
- Elhamifar, Dawood,Kazempoor, Somayeh
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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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- Organic-inorganic hybrid polyoxometalate and its graphene oxide-Fe3O4 nanocomposite, synthesis, characterization and their applications as nanocatalysts for the Knoevenagel condensation and the synthesis of 2,3-dihydroquinazolin-4(1: H)-ones
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The simple and high yield synthesis of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O (PPD = p-phenylenediamine) as a new organic-inorganic hybrid polyoxometalate is reported. The new compound consists of trimetal-substitution polyoxometalate of A-β-SiW9Cu3O3710-, water molecules and coordinated and noncoordinated PPD molecules. H6Cu2[PPD]6[SiW9Cu3O37]·12H2O was firmly grafted on graphene oxide decorated with Fe3O4 nanoparticles. These nanocomposites were characterized by elemental analyses, thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), X-ray photoelectron spectrum (XPS), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), and alternating gradient force magnetometer (AGFM). The results indicate that the size range of the nanoparticles are between 20 and 60 nm. The catalytic activity of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O and the magnetically reusable nanocomposite of GO@Fe3O4@H6Cu2[PPD]6[SiW9Cu3O37]·12H2O were investigated in the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
- Khoshnavazi, Roushan,Bahrami, Leila,Havasi, Forugh
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p. 100962 - 100975
(2016/11/09)
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- Polyoxometalate-Intercalated Layered Double Hydroxides as Efficient and Recyclable Bifunctional Catalysts for Cascade Reactions
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The polyoxometalate (POM) intercalated layered double hydroxides (LDHs) have been widely used as heterogeneous catalysts. However, the application of POM-LDHs as bifunctional catalysts for cascade reaction has seldom been studied compared to the noble-metal-based catalysts. Herein, a series of POM-LDHs catalysts of Tris-LDH-X4(PW9)2 (X=Mn, Fe, Co, Ni, Cu, and Zn; Tris=Tris(hydroxymethtyl)aminomethane) have been prepared. The efficacy of Tris-LDH-Zn4(PW9)2 as efficient bifunctional catalyst has been demonstrated for cascade reactions involving oxidation of benzyl alcohol to benzaldehyde followed by Knoevenagel condensation with ethyl cyanoacetate to produce benzylidene ethyl cyanoacetate. The combination of POM's redox/acidic sites and LDHs's basic sites led to a composite catalyst with excellent activity (99 %) and selectivity (≥99 %) under mild and soluble-base-free conditions. This work offers a new design strategy for the fabrication of efficient bifunctional catalysts for the promotion of one-pot cascade reactions.
- Liu, Kai,Xu, Yanqi,Yao, Zhixiao,Miras, Haralampos N.,Song, Yu-Fei
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p. 929 - 937
(2016/03/15)
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- Amines functionalized C60 as solid base catalysts for Knoevenagel condensation with high activity and stability
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Four kinds of amines functionalized C60 were prepared through an amination reaction of C60 with organic amines. Their surface structures and basic properties were studied by Fourier transform infrared spectrometry (FTIR), X-ray photoelectron spectroscopy (XPS) and temperature-programmed desorption (TPD) with CO2 as the probe molecule. When used as solid base catalysts, N-aminoethylpiperazine functionalized C60 (C60-AEP) showed the best catalytic activity in the Knoevenagel condensation reaction due to the highest basic strength. In addition, the C60-AEP catalyst also showed impressive catalytic stability. All these features endowed C60-AEP with characteristics of both homogeneous and heterogeneous catalysts. More interestingly, chiral l-lysine functionalized C60 (C60-L-L) can be used for asymmetric intermolecular aldol reactions.
- Sun, Yongbin,Cao, Changyan,Huang, Peipei,Yang, Shuliang,Song, Weiguo
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p. 86082 - 86087
(2015/11/03)
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- First report of the application of simple molecular complexes as organo-catalysts for Knoevenagel condensation
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A series of molecular complexes have been designed, synthesized and used as organo-catalysts for the first time for very efficient Knoevenagel condensation. Molecular complexes are thermally stable, easily recyclable, and have a low cost of preparation. T
- Panja, Sumit Kumar,Dwivedi, Nidhi,Saha, Satyen
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p. 65526 - 65531
(2015/08/18)
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- Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.
- Kiyani, Hamzeh,Ghorbani, Fatemeh
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p. 7847 - 7882
(2015/02/19)
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- Synthesis of KOH/SnO2 solid superbases for catalytic Knoevenagel condensation
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KOH/SnO2 solid superbases of specific morphology and uniform pore structure were synthesized. The SnO2 support was prepared by reflux digestion using graphene oxide as template and employed for the loading of KOH by means of grinding
- Xie, Jun,Chen, Lang,Au, Chak-Tong,Yin, Shuang-Feng
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- Facile One-Pot Synthesis of Amine-Functionalized Mesoporous Silica Nanospheres for Water-Medium Knoevenagel Reaction Under Microwave Irradiation
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Amine-functionalized mesoporous silica nanospheres (~80 nm) (NH2-MSNS) were prepared by a co-condensation method using tetraethyl orthosilicate and aminopropyltrimethoxysilane. The catalytic activities of the NH2-MSNS catalysts were
- Zhu, Fengxia,Sun, Xiaojun,Lou, Fengwen,An, Litao,Zhao, Pusu
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p. 1072 - 1079
(2015/02/05)
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- A mechanochemical approach for the construction of carbon-carbon double bonds: Efficient syntheses of aryl/heteroaryl/aliphatic acrylates and nitriles
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An efficient method for the construction of carbon-carbon double bond has been developed from aromatic aldehydes and compounds with active methylene moieties in the presence of catalytic amount of solid sodium ethoxide via mechanochemical approach. This c
- Jayalakshmi, Lakshmi Narayanan,Karuppasamy, Ayyanar,Stalindurai, Kesavan,Sivaramakarthikeyan, Ramar,Devadoss, Vellasamy,Ramalingan, Chennan
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p. 1322 - 1330
(2017/12/02)
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- Basic polymerized imidazolide-based ionic liquid: An efficient catalyst for aqueous Knoevenagel condensation
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A novel basic polymerized ionic liquid (BPIL): polymeric 1-[(4-ethenylphenyl)methyl]-3-propylimidazolium imidazolide was synthesized and characterized by Fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR) and electron spray ionization ma
- Ding, Libing,Li, Hansheng,Zhang, Yaping,Zhang, Kun,Yuan, Hong,Wu, Qin,Zhao, Yun,Jiao, Qingze,Shi, Daxin
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p. 21415 - 21421
(2015/03/18)
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- Direct Three-Component Synthesis of α-Cyano Acrylates Involving Cascade Knoevenagel Reaction and Esterification
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A direct three-component approach has been developed for the synthesis of α-cyano acrylates starting from aldehydes, alcohols and α-cyano acetamide by employing cyanuric chloride as an organocatalyst. A class of structurally diverse α-cyano acrylates have been provided with good to excellent yields via the cascade transformation of Knoevenagel condensation and amide esterification.
- Jing, Yanfeng,Meng, Jiaojiao,Liu, Yunyun,Wan, Jie-Ping
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p. 1194 - 1198
(2015/11/02)
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- Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst
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Solid phase synthesis of poly(propylene imine) dendrimer is described. An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amin
- Gopalakrishna Panicker, Rajesh Krishnan,Krishnapillai, Sreekumar
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supporting information
p. 2352 - 2354
(2014/05/06)
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- Synthesis, characterization and heterogeneous catalytic activity of diamine-modified silica-coated magnetite-polyoxometalate nanoparticles as a novel magnetically-recoverable nanocatalyst
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Magnetite-polyoxometalate hybrid nanomaterials, Fe3O 4@SiO2@NH-NH2-PW, was prepared by grafting of H3PW12O40 on the diamine-functionalized Fe 3O4 magnetite
- Shahbazi, Fomeida,Amani, Kamal
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- Nano-Fe3O4 encapsulated-silica particles bearing 3-aminopropyl group as a magnetically separable catalyst for efficient knoevenagel condensation of aromatic aldehydes with active methylene compounds
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Knoevenagel condensation of aromatic aldehydes with active methylene compounds such as malononitrile, ethylcyanoacetate, benzimidazol-2-acetonitrile and benzothiazole-2-acetonitrile proceeded very smoothly, catalyzed by nano-Fe3O4 encapsulated-silica particles supported primary amine. Both reaction time and yield are satisfying. The advantages of this catalyst are ease of preparation, non-toxicity, low cost, ease of handling and recyclability. Copyright
- Liu, Shuo,Ni, Yuxiang,Yang, Jianguo,Hu, Huanan,Ying, Anguo,Xu, Songlin
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p. 343 - 348
(2014/05/20)
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- One-pot synthesis of potassium-loaded MgAl oxide as solid superbase catalyst for Knoevenagel condensation
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We report a new strategy for one-pot synthesis of potassium-loaded MgAl oxides using KOH to adjust the pH value of the reaction system. The as-prepared solid superbases were studied by N2 physisorption method, energy-dispersive X-ray spectrosco
- Zhao, Jin,Xie, Jun,Au, Chak-Tong,Yin, Shuang-Feng
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- One-by-one hydrogenation, cross-coupling reaction, and Knoevenagel condensations catalyzed by PdCl2 and the downstream palladium residue
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A novel catalyst-economic strategy with a recovered palladium catalyst was successfully applied for multi-task and maximum reuse in different types of one-by-one downstream reactions, from catalytic hydrogenation to Suzuki and Sonogashira-type cross-coupling reactions, Knoevenagel condensations, and trans-Knoevenagel-like condensations.
- Wang, Hu,Li, Li,Bai, Xing-Feng,Deng, Wen-Hui,Zheng, Zhan-Jiang,Yang, Ke-Fang,Xu, Li-Wen
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supporting information
p. 2349 - 2355
(2013/09/12)
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- Novel magnetic nanoparticles Fe3O4-immobilized domino Knoevenagel condensation, Michael addition, and cyclization catalyst
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The synthesis, characterization and applications of guanidine supported on magnetic nanoparticles Fe3O4 (MNPs-Guanidine) as a novel magnetically separable base nanocatalyst are described. We have studied the application of this new c
- Rostami, Amin,Atashkar, Bahareh,Gholami, Hoshyar
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- Ammonium fluoride as an inexpensive catalyst for Knoevenagel condensation in solvent-free conditions under microwave irradiation
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Ammonium fluoride (NH4F) has been found to be an inexpensive catalyst for Knoevenagel condensation between aromatic aldehydes 1 and active methylene compounds 2 to afford arylidene derivatives 3 in excellent yields.
- Mogilaiah,Vinay Chandra,Jagadeeshwar,Kavitha
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p. 694 - 697
(2013/07/05)
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- A PEG bridged tertiary amine functionalized ionic liquid exhibiting thermoregulated reversible biphasic behavior with cyclohexane/isopropanol: Synthesis and application in Knoevenagel condensation
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A novel poly(ethylene glycol) bridged tertiary amine functionalized ionic liquid PEG800-DPIL(Cl) was synthesized. It can form a temperature driven reversible biphasic system with cyclohexane/isopropanol mixed solvent. This biphasic system was applied in Knoevenagel condensation up to 99%. PEG 800-DPIL(Cl) could be simply recovered and recycled for several runs.
- Luo, Jun,Xin, Tantan,Wang, Yinglei
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p. 269 - 273
(2013/02/25)
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- Further studies toward himandrine via sequential oxidative amidation-intramolecular Diels-Alder reactions
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Exploratory work toward the alkaloid himandrine evaluated the directing ability of a pyrrolidine C-3 substituent in a diastereotopic group elective intramolecular Diels-Alder reaction of a spirodienone obtained by the oxidative amidation of a phenol. The
- Kasahara, Takahito,Ciufolini, Marco A.
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supporting information
p. 82 - 90
(2013/03/14)
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- Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles
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A new metathesis reaction of azomethine imines is found. Catalytic or thermal diaziridine ring opening of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes leads to azomethine imines reacting further with het(aryl)methylidenemalononitriles to give in situ new azomethine imines inaccessible by common synthetic methods. New azomethine imines are detected as pyrazolines formed via a 1,4-H shift and trapped by the [3+2] cycloaddition with various dipolarophiles to yield 1,5-diazabicyclo[3.3.0]octane derivatives bearing pharmacophoric heterocycles, e.g. furan, nitrofuran, thiophene, and indole. The best results are achieved in the Et2O·BF3-catalyzed reactions in ionic liquids.
- Pleshchev,Petukhova,Kuznetsov,Khakimov,Pivina,Nelyubina,Makhova
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p. 1066 - 1075
(2014/03/21)
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