- 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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- Novel synthesis of 3-cyano-2-pyridones derivatives catalyzed by Au–Co/TiO2
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Abstract: The current work described a new and highly selective method for the synthesis of substituted 3-cyano-2-pyridones scaffolds using gold-cobalt supported on TiO2 as a robust and recyclable catalyst. The products were successfully obtained by one-pot, multicomponent manner. This procedure generated the desired products 2-pyridones derivatives in good yields, from simple and available starting materials using heterogeneous and reusable catalyst. The diversity of 3-cyano-2-pyridones derivatives was prepared and characterized by IR, 1H and 13C NMR data and confirmed by element analysis data. Graphic abstract: [Figure not available: see fulltext.].
- Mehiaoui, Nawel,Kibou, Zahira,Berrichi, Amina,Bachir, Redouane,Choukchou-Braham, Noureddine
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p. 5263 - 5280
(2020/09/21)
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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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- Asymmetric Reaction of p-Quinone Diimide: Organocatalyzed Michael Addition of α-Cyanoacetates
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Hitherto unknown catalytic enantioselective transformation of p-quinone diimides is achieved using chiral bifunctional organic molecules. Bifunctional thiourea compounds catalyze the Michael addition of cyanoacetates with excellent yields and enantioselec
- Reddy, Sivakumar N.,Reddy, Venkatram R.,Dinda, Shrabani,Nanubolu, Jagadeesh Babu,Chandra, Rajesh
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supporting information
p. 2572 - 2575
(2018/05/17)
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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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- 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, 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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- Kinetic insights of DNA/RNA segment salts catalyzed knoevenagel condensation reaction
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In this work, we demonstrated that (i) salts of RNA/DNA segments were capable of catalyzing Knoevenagel condensation at physiological pH 7.0 with efficiency comparable to one of the best enzymes, porcine pancreatic lipase (PPL); and (ii) a broad scope of
- Li, Weina,Fedosov, Sergey N.,Tan, Tianwei,Xu, Xuebing,Guo, Zheng
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p. 3294 - 3300
(2014/12/11)
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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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- Sodium benzoate as a green, efficient, and recyclable catalyst for knoevenagel condensation
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Sodium benzoate was utilized as a novel efficient and green catalyst for the Knoevenagel condensation of aldehydes with active methylene compounds such as ethyl cyanoacetate and malononitrile to afford substituted olefins through the conventional stirring
- Liu, Qing,Ai, Hong-Mei
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experimental part
p. 3004 - 3010
(2012/07/27)
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- Knoevenagel condensation catalyzed by sodium silicate under solvent-free conditions
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Sodium silicate pentahydrate has been utilized as an efficient catalyst for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds to afford substituted olefins in yields of 80.6%~98.9% under solvent-free conditions at room tem
- Liu, Qing,Han, Yinfeng
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experimental part
p. 2033 - 2037
(2011/11/30)
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- A simple, efficient, and green protocol for Knoevenagel condensation in a cost-effective ionic liquid 2-hydroxyethlammonium formate without a catalyst
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Knoevenagel condensation of aromatic aldehydes with active methylene compounds such as malononitrile, ethylcyanoacetate, and cyanoacetamide proceeded very smoothly in reusable and cheap ionic liquid 2-hydroxyethylammonium formate at room temperature in the absence of a catalyst. Compared to other reported ionic liquids, the ionic liquid 2-hydroxyethylammonium formate shows better potential in the applications on the industrial scale with its low cost and viscosity.
- Ying, Anguo,Liang, Huading,Zheng, Renhua,Ge, Changhua,Jiang, Huajiang,Wu, Chenglin
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experimental part
p. 579 - 585
(2012/05/05)
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- Synthesis of highly stable CoFe2O4 nanoparticles and their use as magnetically separable catalyst for Knoevenagel reaction in aqueous medium
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Synthesis of spinel cobalt ferrite magnetic nanoparticles (MNPs) with average sizes in the range 40-50 nm has been achieved using a combined sonochemical and co-precipitation technique in aqueous medium without any surfactant or organic capping agent. The nanoparticules form stable dispersions in aqueous or alcoholic medium. The uncapped nanoparticles were utilized directly as a reusable catalyst for Knoevenagel reaction in aqueous ethanol (1:3). Compartmentation and recovery of the catalyst from reaction medium was done with the aid of an external magnet. High yield of corresponding Knoevenagel products were obtained within a very short time in presence of just 5 mol% of the catalyst at 50 °C.
- Senapati, Kula Kamal,Borgohain, Chandan,Phukan, Prodeep
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experimental part
p. 24 - 31
(2011/05/17)
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- Simple, efficient, and green procedure for the knoevenagel condensation catalyzed by ethylenediammonium diacetate under solvent-free conditions
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A simple, efficient, and green procedure for Knoevenagel condensation of aromatic aldehydes with malononitrile and ethyl cyanoacetate catalyzed by ethylenediammonium diacetate under solvent-free conditions at room temperature is reported. This method give
- Zhou, Zhongqiang,Sun, Yong
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experimental part
p. 3162 - 3168
(2011/09/30)
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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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- Green and efficient Knoevenagel condensation catalysed by a DBU based ionic liquid in water
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An effi cient, clean and facile protocol for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalysed by task specifi c ionic liquid 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate in an aqueous medium has been developed. The reactions proceed at room temperature and high to excellent yields were afforded. The work-up procedure is very simple. The ionic liquid could be recycled for 10 runs without noticeably loss of its catalytic activity.
- Ying, An-Guo,Wang, Li-Min,Wang, Le-Le,Chen, Xin-Zhi,Ye, Wei-Dong
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experimental part
p. 30 - 33
(2010/05/19)
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- L-Histidine and L-arginine promote Knoevenagel reaction in water
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Histidine and arginine were applied to the synthesis of trisubstituted alkenes through a condensation of an aldehyde with an activated CH-acid such as ethyl cyanoacetate, malononitrile, acetyl acetone or ethyl ace-toacetate during 5-12 h in water at room
- Rahmati, Abbas,Vakili, Kobra
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experimental part
p. 911 - 916
(2010/11/05)
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- Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands
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Eight new 5-arylidene-3-benzyl-thiazolidine-2,4-diones with halide groups on their benzyl rings were synthesized and assayed in vivo to investigate their anti-inflammatory activities. These compounds showed considerable biological efficacy when compared to rosiglitazone, a potent and well-known agonist of PPARγ, which was used as a reference drug. This suggests that the substituted 5-arylidene and 3-benzylidene groups play important roles in the anti-inflammatory properties of this class of compounds. Docking studies with these compounds indicated that they exhibit specific interactions with key residues located in the site of the PPARγ structure, which corroborates the hypothesis that these molecules are potential ligands of PPARγ. In addition, competition binding assays showed that four of these compounds bound directly to the ligand-binding domain of PPARγ, with reduced affinity when compared to rosiglitazone. An important trend was observed between the docking scores and the anti-inflammatory activities of this set of molecules. The analysis of the docking results, which takes into account the hydrophilic and hydrophobic interactions between the ligands and the target, explained why the 3-(2-bromo-benzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-di one compound had the best activity and the best docking score. Almost all of the stronger hydrophilic interactions occurred between the substituted 5-arylidene group of this compound and the residues of the binding site.
- Barros, Cleiton Diniz,Amato, Angélica Amorim,Oliveira, Tiago Bento de,Iannini, Karime Bicas Rocha,Silva, Anekécia Lauro da,Silva, Teresinha Gon?alves da,Leite, Elisa Soares,Hernandes, Marcelo Zaldini,Lima, Maria do Carmo Alves de,Galdino, Suely Lins,Neves, Francisco de Assis Rocha,Pitta, Ivan da Rocha
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experimental part
p. 3805 - 3811
(2010/08/06)
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- A novel and green method for the synthesis of highly substituted isoquinoline derivatives in ionic liquid
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(Chemical Equation Presented) A series of new highly substituted isoquinoline derivatives was obtained from the reaction of 2-(1-substituted piperidin-4-ylidene)malononitrile, benzaldehyde and malononitrile or cyanoacetate in ionic liquid at 50°C. This no
- Wang, Xiang-Shan,Wu, Jian-Rong,Li, Qing,Zhang, Mei-Mei
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body text
p. 1355 - 1363
(2010/03/26)
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- 7-Methyl trimethoprim analogues as inhibitors of the folate metabolizing enzymes
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A series of 5-(1-phenylethyl)pyrimidines 2-10 (Table I) were designed and synthesized as potent and selective inhibitors of Pneumocystis carinii (P. carinii), Toxoplasma gondii (T. gondii) and Mycobacterium avium (M. avium) dihydrofolate reductases (DHFR)
- Gangjee, Aleem,Lin, Xin,Queener, Sherry F.
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p. 507 - 512
(2007/10/03)
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- The Knoevenagel condensation of aromatic aldehydes with malononitrile or ethyl cyanoacetate in the presence of CTMAB in water
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A new route of Knoevenagel condensation of aldehydes with malononitrile or ethyl cyanoacetate in the presence of CTMAB in water is described. CTMAB is the most effective catalyst to increase yield among CTMAB, BTEAC and TBAI.
- Wang,Ren,Cao,Tong
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p. 673 - 677
(2007/10/03)
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- Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans
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A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineeth anol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2 nM for inhibition of dopamine uptake.
- Bogeso
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p. 935 - 947
(2007/10/02)
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