- Selenotungstates incorporating organophosphonate ligands and metal ions: synthesis, characterization, magnetism and catalytic efficiency in the Knoevenagel condensation reaction
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Three sandwich-type TM-containing (TM = transition metal) organophosphonate-based polyoxotungstate clusters, [TM(H2O)4(SeW6O21)2{Co(OOCCH2NCH2PO3)2}3]12?(TM = Co, Ni), have been successfully synthesized, which are the first reported TM-containing organophosphonate-based selenotungstates. They were structurally characterized by PXRD analyses, IR spectroscopy, TGA analyses,etc. Magnetic measurements show that all three compounds exhibit antiferromagnetic interactions. Besides,Co1can be used as an efficient heterogeneous catalyst in the Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate under mild conditions (60 °C), and exhibits satisfactory conversion (93%) and high selectivity (99%).
- Ban, Ran,He, Peipei,Kong, Hui,Ma, Pengtao,Niu, Jingyang,Wang, Jiawei,Wang, Jingping,Xu, Qiaofei,Yang, Zongfei
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supporting information
p. 7420 - 7425
(2020/06/21)
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- Synthesis of multifunctional polymer containing Ni-Pd NPs via thiol-ene reaction for one-pot cascade reactions
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Recently, acid–base bifunctional catalysts have been considered due to their abilities, such as the simultaneous activation of electrophilic and nucleophilic species and their high importance in organic syntheses. However, the synthesis of acid–base catalysts is problematic due to the neutralization of acidic and basic groups. This work reports a facial approach to solve this problem via the synthesis of a novel bifunctional polymer using inexpensive materials and easy methods. In this way, at the first step, heterogeneous poly (styrene sulfonic acid-n-vinylimidazole) containing pentaerythritol tetra-(3-mercaptopropionate) (PETMP) and trimethylolpropane trimethacrylate (TMPTMA) cross-linkers were synthesized in the pores of a mesoporous silica structure using click reaction as a novel bifunctional acid–base catalyst. After that, Ni-Pd nanoparticles supported on poly (styrenesulfonic acid-n-vinylimidazole)/KIT-6 as a novel trifunctional heterogeneous acid–base-metal catalyst was prepared. The prepared catalysts were characterized by various techniques like FT-IR, TGA, ICP-AES, DRS-UV, TEM, FE-SEM, EDS-Mapping, and XRD. The synthesized catalysts were efficiently used as bifunctional/trifunctional catalysts for one-pot, deacetalization-Knoevenagel condensation and one-pot, three-step and a sequential reaction containing deacetalization-Knoevenagel condensation-reduction reaction. It is important to note that the synthesized catalyst showing high chemo-selectivity for the reduction of nitro group, alkenyl double bond and ester group in the presence of nitrile. Moreover, it was found that the different nanoparticles including Ni, Pd, and alloyed Ni-Pd showing different chemo-selectivity and catalytic activity in the reaction.
- Javad Kalbasi, Roozbeh,Mesgarsaravi, Niloofar,Gharibi, Reza
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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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- Layered double hydroxide anchored ionic liquids as amphiphilic heterogeneous catalysts for the Knoevenagel condensation reaction
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In recent years, great attention has been dedicated to the development of heterogeneous base catalysts providing a green and sustainable process in benign aqueous media. Herein, the ionic liquid modified layered double hydroxide (LDH) based catalysts of L
- Li, Tengfei,Zhang, Wei,Chen, Wei,Miras, Haralampos N.,Song, Yu-Fei
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supporting information
p. 3059 - 3067
(2018/03/06)
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- Fine tuning of catalytic and sorption properties of metal-organic frameworks via in situ ligand exchange
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Metal-organic frameworks (MOFs) are gaining considerable attention not only because of their diverse structures but also due to their interesting properties and potential applications. However, fabrication of MOFs with desired structures and properties re
- Wang, Peng,Chen, Kai,Liu, Qing,Wang, Huai-Wei,Azam, Mohammad,Al-Resayes, Saud I.,Lu, Yi,Sun, Wei-Yin
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supporting information
p. 11425 - 11430
(2017/09/07)
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- A carboxylate-rich metalloligand and its heterometallic coordination polymers: Syntheses, structures, topologies, and heterogeneous catalysis
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This work reports three heterometallic coordination polymers (HCPs), namely, [{(1′)2Zn8Na2(H2O)21}·20H2O]n (2), [{(1′)(1')Cd8(H2O)21}·32H2/
- Srivastava, Sumit,Kumar, Vijay,Gupta, Rajeev
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p. 2874 - 2886
(2016/06/01)
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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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- Discovery, stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinolines as novel selective κ opioid receptor agonists
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A novel series of 1-(pyrrolidin-1-ylmethyl)-2-[(3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinoline derivatives maj-3a-maj-3u were synthesized and evaluated in vitro for their binding affinity at κ-opioid receptors. Maj-3c displayed the highest affinity for κ-opioid receptors (Ki = 0.033 nM) among all the compounds evaluated. Furthermore, all four stereoisomers of compound 3c were prepared, and (1S,18S)-3c was identified as the most potent (Ki = 0.0059 nM) κ-opioid receptor agonist among the four stereoisomers. Maj-3c produced significant antinociception (ED50 = 0.000406 mg kg-1) compared to U-50,488H and original BRL 52580 in the acetic acid writhing assay, but its strong sedative effect (ED50 = 0.000568 mg kg-1) observed in the mouse rotation test reduced its druggability. To minimize the central nervous system side effects, a series of hydroxyl-containing analogs of maj-3c were synthesized, and maj-11a was found to be a potent κ-opioid receptor agonist (Ki = 35.13 nM). More importantly, the dose for the sedative effect (ED50 = 9.29 mg kg-1) of maj-11a was significantly higher than its analgesic dose (ED50 = 0.392 mg kg-1), which made it a promising peripheral analgesic candidate compound with weak sedative side effects.
- Gan, Zong-Jie,Wang, Yu-Hua,Xu, Yun-Gen,Guo, Ting,Wang, Jun,Song, Qiao,Xu, Xue-Jun,Hu, Shi-Yuan,Wang, Yu-Jun,Wang, De-Chuan,Sun, De-Zhu,Zhang, Di,Xi, Tao,Li, Hao-Dong,Zhang, Hai-Bo,Hang, Tai-Jun,Lu, Hong-Guo,Liu, Jing-Gen
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p. 5656 - 5673
(2015/05/27)
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- A simple, efficient and green procedure for knoevenagel condensation in hydroxy-functionalized ionic liquids
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An efficient and simple Knoevenagel condensation catalyzed by hydroxy-functionalized ionic liquids proceeded smoothly in high yields under ambient and solvent-free conditions. The condensation procedures of aryl aldehydes and 2,4-thiazolidinedione was involved in hydrogen bonding interactions between the hydroxy groups of the ILs and the carbonyl group of the aldehyde. The ionic liquids can be reused for five times without significant loss in activity.
- Liu, Yuting,Li, Rong,Xing, Yanjun
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p. 1385 - 1397
(2015/07/15)
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- Knoevenagel condensation reaction using ionic liquid [ADPQ][CF3SO3] as green and reusable catalyst
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Knoevenagel condensation reaction of aromatic aldehydes with some active methylene compounds proceeded efficiently without solvent using ionic liquids as catalyst. The experimental results show that these ionic liquids have good catalytic activities to th
- Gao, Xiaochong,Gao, Can,Gao, Ruichang
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p. 2145 - 2148
(2015/11/28)
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- Classical Keggin Intercalated into Layered Double Hydroxides: Facile Preparation and Catalytic Efficiency in Knoevenagel Condensation Reactions
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The family of polyoxometalate (POM) intercalated layered double hydroxide (LDH) composite materials has shown great promise for the design of functional materials with numerous applications. It is known that intercalation of the classical Keggin polyoxome
- Jia, Yueqing,Fang, Yanjun,Zhang, Yingkui,Miras, Haralampos N.,Song, Yu-Fei
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p. 14862 - 14870
(2015/10/20)
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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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- 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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- Tri-lacunary polyoxometalates of Na8H[PW9O 34] as heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation and the synthesis of benzoxazole derivatives
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We reported for the first time the development of tri-lacunary polyoxometalates (POMs) of Na8H[A-PW9O34] ·7H2O and Na8H[B-PW9O 34]·19H2O (Na-A-PW9 and Na-B-PW 9) as highly selective and efficient heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation of various aldehydes and ketones and the synthesis of benzoxazole derivatives at 25 C under mild conditions. Since both Na-A-PW9 and Na-B-PW9 display no characteristic porosity, it is proposed that the catalytic reactions proceed not only on the surface and interface, but also in the bulk phase. The catalysts can be easily recovered and reused for at least six times without obvious decrease of catalytic activities and the structures of the catalysts remain unchanged after recycling. The easy preparation, high efficiency, reusability of the heterogeneous catalysts of Na-A-PW9 and Na-B-PW9 exhibit great potential for further application.
- Zhao, Shen,Chen, Yang,Song, Yu-Fei
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p. 140 - 146
(2014/03/21)
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- Efficient and reusable amine-functionalized polyacrylonitrile fiber catalysts for Knoevenagel condensation in water
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A series of new fiber catalysts has been synthesized by aminating a commercially available polyacrylonitrile fiber with polyamines such as diethylenetriamine and triethylenetetramine. These fiber catalysts can efficiently catalyze the Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate in water (yields: 95-98%). The triethylenetetramine aminated fiber catalyst was used to catalyze the condensations of a wide range of aromatic aldehydes and active methylene compounds and in each case, this catalyst performed well with yields higher than 93%. This fiber catalyst also exhibited excellent reusability (up to 21 times) and photostability.
- Li, Guowei,Xiao, Jia,Zhang, Wenqin
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experimental part
p. 2234 - 2242
(2012/09/10)
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- Efficient asymmetric synthesis of 4H-chromene derivatives through a tandem michael addition-cyclization reaction catalyzed by a salen-cobalt(II) complex
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The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates. Moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee) were obtained with a chiral salen-cobalt(II) complex. This process was air tolerant and easily performed, which provides an efficient method for the synthesis of chiral 4H-chromene derivatives. The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates catalyzed by a chiral salen-cobalt(II) complex with moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee).
- Dong, Zhenhua,Liu, Xiaohua,Feng, Juhua,Wang, Min,Lin, Lili,Feng, Xiaoming
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supporting information; experimental part
p. 137 - 142
(2011/03/18)
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- PROCESS FOR THE PREPARATION OF 1-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVES
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A process for the preparation of 1-phenyl-3-dimethylaminopropane derivatives of formula (I) and its pharmaceutically acceptable salts thereof from cyano intermediate of formula (II), wherein R1 can be selected from -OR2, halo, -CH2OR2, -SR2, -SOR2, SO2R2, -SO3H, -NO2, -NR2R2', -CONR2R2', carboxylic esters, sulfonate esters or phosphate esters, R2 and R2' can be same or different, and can be selected from hydrogen, alkyl, aryl, aralkyl, heteroaryl, -COR2", -P03(R2")2 wherein R2" can be selected from alkyl, aryl, aralkyl, heteroaryl and the like.
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Page/Page column 35
(2011/07/30)
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- Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: Synthesis of multisubstituted cyclohexenes
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From our investigations on phosphine-catalyzed [4+2] annulations between α-alkyl allenoates and activated olefins for the synthesis of cyclohexenes, we discovered a hexamethylphosphorous triamide (HMPT)-catalyzed [4+2] reaction between α-alkyl allenoates
- Tran, Yang S.,Martin, Tioga J.,Kwon, Ohyun
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body text
p. 2101 - 2106
(2011/10/11)
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- Knoevenagel condensation catalyzed by a tertiary-amine functionalized polyacrylonitrile fiber
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A new fiber catalyst for Knoevenagel condensation has been prepared by aminating a commercially available polyacrylonitrile fiber with N,N-dimethyl-1,3-propanediamine. The fiber catalyst was characterized by elemental analysis, X-ray powder diffraction spectra (XRD), scanning electron microscopy (SEM) and Fourier-transfer infrared spectroscopy (FTIR). The Knoevenagel condensation proceeded smoothly in the presence of the fiber catalyst and the products were obtained in excellent yields. This catalyst is applicable to a wide range of aromatic aldehydes. Moreover, the reaction can be easily carried out in different solvents of varying polarities. The newly developed fiber catalyst was also found to exhibit excellent recyclability and reusability (up to 10 times) without any additional treatment.
- Li, Guowei,Xiao, Jia,Zhang, Wenqin
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experimental part
p. 1828 - 1836
(2011/09/16)
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- TETRAHYDRO ISOQUINOLINE DERIVATIVES, PREPARATION METHODS AND MEDICINAL USES THEREOF
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as κ-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 11
(2009/04/23)
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- Tetrahydro isoquinoline derivatives, preparation methods and medicinal uses thereof
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as kappa-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 8
(2009/12/02)
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- Discovery of 4-aryl-2-oxo-2H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay
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As a continuation of our efforts to discover and develop the apoptosis inducing 4-aryl-4H-chromenes as potential anticancer agents, we explored the removal of the chiral center at the 4-position and prepared a series of 4-aryl-2-oxo-2H-chromenes. It was f
- Kemnitzer, William,Jiang, Songchun,Zhang, Hong,Kasibhatla, Shailaja,Crogan-Grundy, Candace,Blais, Charles,Attardo, Giorgio,Denis, Real,Lamothe, Serge,Gourdeau, Henriette,Tseng, Ben,Drewe, John,Cai, Sui Xiong
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scheme or table
p. 5571 - 5575
(2009/05/30)
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- Solvent-free L-proline catalysed condensation of ethyl cyanoacetate with aldehydes
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Solvent-free Knoevenagel condensation of ethyl cyanoacetate with aromatic aldehydes, catalysed by environmentally friendly silica gel supported L-proline under microwave irradiation is studied.
- Oskooie, Hossein A.,Roomizadeh, Elham,Heravi, Majid M.
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p. 246 - 247
(2007/10/03)
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- Design, synthesis, and monoamine transporter binding site affinities of methoxy derivatives of indatraline
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A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline
- Gu,Yu,Jacobson,Rothman,Dersch,George,Flippen-Anderson,Rice
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p. 4868 - 4876
(2007/10/03)
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- Synthesis and antileishmanial activity of α-cyano ethyl propenoates - A new class of antileishmanials
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A number of α-cyano-β-substituted ethyl propenoates were synthesised by condensation of appropriate aldehydes with ethyl cyanoacetate in basic medium. These compounds have been studied for their antileishmanial activities in vivo in hamsters. Two compound
- Tiwari, Suman,Gupta, Suman,Tripathi, Rama P.,Khan, Abdul R.,Katiyar, Jagdish Chandra,Bhaduri, Amiya P.
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p. 144 - 148
(2007/10/03)
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- Solvent-free microwave enhanced Knoevenagel condensation of ethyl cyanoacetate with aldehydes
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A high yielding and fast method of Knoevenagel condensation of ethyl cyanoacetate with various aldehydes under microwave irradiation using environment-friendly ammonium acetate in the absence of any solvent is described.
- Mitra, Alok Kumar,De, Aparna,Karchaudhuri, Nilay
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p. 2731 - 2739
(2007/10/03)
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- Aldol and Knoevenagel condensations catalysed by modified Mg-Al hydrotalcite: a solid base as catalyst useful in synthetic organic chemistry
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Aldol and Knoevenagel condensations were performed with suitably activated Mg-Al hydrotalcite as catalyst in quantitative yields in the liquid phase under mild reaction conditions at a faster rate for the first time.
- Kantam, M. Lakshmi,Choudary, B. M.,Reddy, Ch. Venkat,Rao, K. Koteswara,Figueras, F.
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p. 1033 - 1034
(2007/10/03)
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- Palladium catalyzed regioselective β-acetonation-α-allylation of activated olefins in one shot
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The reaction of certain activated olefins 4 with allyl acetoacetate 5 in the presence of catalytic amounts of Pd(PPh3)4 (5 mol %) in THF at room temperature gave the corresponding β-acetonated α-allylated double addition products 6 regioselectively in good to excellent yields. The nature of the electron-withdrawing group in activated olefins affected significantly the reactivity of substrates; at least one of two electron-withdrawing groups of 4 should be a CN group. A proposed mechanism for this unprecedented three- component coupling reaction involves oxa-π-allyl-π-allylpalladium intermediate 3a (or its synthetic equivalents 3b-d). The in situ generation of activated olefins 4, from the aldehyde 11 and malononitrile 12, followed by the palladium-catalyzed reaction with allyl acetoacetate 5 also worked well, producing the corresponding three-component coupling products in good yields. Furthermore, allyltributylstannane 13 and α-chloro acetone 14 could be used as the α-allylation and β-acetonation components, respectively, instead of allyl acetoacetate 5. The scope and limitations of palladium- catalyzed regioselective β-acetonation-α-allylation reaction of activated olefins are described.
- Shim, Jae-Goo,Nakamura, Hiroyuki,Yamamoto, Yoshinori
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p. 8470 - 8474
(2007/10/03)
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- Synthesis of cis-4-methyl-3-phenylpyrrolidines as potential dopaminergic agonists
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cis-3-(3,4-Dihydroxyphenyl)-4-methyl-l-(n-propyl)pyrrolidine (23) was synthesized and evaluated for dopaminergic activity. The synthesis of 23 involved selective 4-acylation of the 3-phenylpyrrolidine-2,5-dione 15 and cis-addition of hydrogen to a 4-methy
- Crider,Sylvestri,Tschappat,Dick,Leader
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p. 1407 - 1412
(2007/10/02)
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