- Size control of catalytic reaction space by intercalation of alkylcarboxylate anions into Ni-Zn mixed basic salt interlayer: Application for knoevenagel reaction in water
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The interlayer space of layered Ni-Zn mixed basic salt (NiZn) can be controlled precisely by the intercalation of various carboxylate anions with long alkyl chains via simple anion exchange. Expansion of interlayer space in the anion-exchanged NiZn depend
- Hara, Takayoshi,Kurihara, Jun,Ichikuni, Nobuyuki,Shimazu, Shogo
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- Preparation of Mesoporous Basic Oxides through Assembly of Monodispersed Mg–Al Layered Double Hydroxide Nanoparticles
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Mesoporous basic Mg–Al mixed metal oxides (MMOs) with a high surface area and large pore size have been prepared through the assembly of monodispersed layered double hydroxide nanoparticles (LDHNPs) with block copolymer templates. The particle sizes of th
- Oka, Yuya,Kuroda, Yoshiyuki,Matsuno, Takamichi,Kamata, Keigo,Wada, Hiroaki,Shimojima, Atsushi,Kuroda, Kazuyuki
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- Nitrogen-containing porous cerium trimetaphosphimate as a new efficient base catalyst
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A new layer nitrogen-containing porous cerium trimetaphosphimate with pendant NH groups projecting into the channels has been synthesized and characterized. Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate is carried out with this complex a
- Yi, Jianglong,Fu, Zhiyong,Liao, Shijun,Song, Desheng,Dai, Jingcao
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- Amine-functionalized go as an active and reusable acid-base bifunctional catalyst for one-pot cascade reactions
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The amine-functionalized graphene oxide was prepared by a facile one-step silylation approach and used as an acid-base bifunctional catalyst in one-pot cascade reactions containing successive acetal hydrolysis and Knoevenagel condensation owing to the separate coexistence of original carboxylic acid on the edge of the GO sheet and the postgrafted amine groups on the GO basal surface. This catalyst exhibited much higher activity than either amine-functionalized active carbon, amine-functionalized SBA-15, or amine-functionalized Al2O3 due to the enriched surface acid sites and the diminished diffusion limitation as well as high catalyst dispersion in liquid solution due to the unique two-dimensional structure. More importantly, this catalyst could be easily recycled and used repetitively, showing potential application in industry.
- Zhang, Fang,Jiang, Huangyong,Li, Xiaoyan,Wu, Xiaotao,Li, Hexing
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- 2-pyrrolidinecarboxylic acid ionic liquid catalyzed knoevenagel condensation
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The pyrrolidinecarboxylic functionalized ionic liquid, 1-butyl-3- methylimidazolium-(S)-2-pyrrolidinecarboxylic acid salt ([bmim][Pro]), was prepared using an improved procedure. α,β-Unsaturated carbonyl compounds were selectively synthesized and high yie
- Song, Hongbing,Yu, Yinghao,Chen, Xuewei,Li, Xuehui,Xi, Hongxia
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- Synthesis of α-Dawson-type silicotungstate [α-Si 2W18O62]8- and protonation and deprotonation inside the aperture through intramolecular hydrogen bonds
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The design of structurally well-defined anionic molecular metal-oxygen clusters, polyoxometalates (POMs), leads to inorganic receptors with unique and tunable properties. Herein, an α-Dawson-type silicotungstate, TBA 8[α-Si2W18
- Minato, Takuo,Suzuki, Kosuke,Kamata, Keigo,Mizuno, Noritaka
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- Comparison of the alkalinity of hydroxypyridine anion-based protic ionic liquids and their catalytic performance for Knoevenagel reaction: The effect of the type of cation and the position of nitrogen atom of anion
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The design of acidity and alkalinity is an important characteristic of ionic liquids, and it also affects their application. For this reason, the alkalinity of six hydroxypyridine anion-based protic ionic liquids (PILs) was determined by potentiometric ti
- Xie, Bin,Xu, Yingjie,Tang, Xiaochen,Shu, Hegang,Chen, Tingting,Zhu, Xiao
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- Continuous flow ZIF-8/NaA composite membrane microreactor for efficient Knoevenagel condensation
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A ZIF-8/NaA composite membrane microreactor was fabricated on multi-channel stainless steel plate. NaA zeolite membrane was first introduced into the microchannel as a modification layer via a secondary growth. Subsequently, a layer of ZIF-8 membrane was
- Zhang, Guangcai,Zhang, Tong,Zhang, Xiongfu,Yeung, King Lun
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- Synthesis, structure, luminescence and catalytic properties of cadmium(ii) coordination polymers with 9H-carbazole-2,7-dicarboxylic acid
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Two Cd(ii) metal-organic frameworks were synthesized from the NH-functionalized dicarboxylate ligand 9H-carbazole-2,7-dicarboxylic acid (2,7-H2CDC). Compound 1, [Cd4(CDC)4(DMF) 4]·4DMF·4H2O, displays
- Yi, Xiu-Chun,Huang, Meng-Xuan,Qi, Yan,Gao, En-Qing
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- Ammonium chloride catalyzed Knoevenagel condensation in PEG-400 as ecofriendly solvent
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A simple and selective green methodology has been successfully developed for Knoevenagel condensation in polyethylene glycol-400 using 10 mol % ammonium chloride as catalyst. The method is applicable to a wide range of aromatic, heteroaromatic and α,β-unsaturated aldehydes. The reactions have been found to be clean and free from the formation of the Michael adduct.
- Waghmare, Smita R.
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p. 849 - 855
(2021/09/28)
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- Introduction of bis-imidazolium dihydrogen phosphate as a new green acidic ionic liquid catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives
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In this work, [H2-Bisim][H2PO4]2 as a novel bis-imidazole-based acidic ionic liquid has been synthesized and characterized with a variety of techniques including FT-IR, 1H, 13C, 31/su
- Rahmatizadeh-Pashaki, Zahra,Daneshvar, Nader,Shirini, Farhad
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p. 2135 - 2149
(2021/02/01)
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- trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines
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trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.
- Sch?mberg, Fritz,Peri?, Milica,Meyer, Maximilian,Vilotijevi?, Ivan
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- Physically mixed catalytic system of amino and sulfo-functional porous organic polymers as efficiently synergistic co-catalysts for one-pot cascade reactions
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In this article, acid/base bi-functional polymeric materials were prepared using physically mixed porous poly(divinylbenzene-co-4-vinylbenzenesulfonic acid) (P(DVB-VBS)) with sulfonic acid groups and poly(divinylbenzene-co-4-vinylbenzyl amine) (P(DVB-VBA)) with amino groups, which were synthesized by solvothermal polymerization of crosslinker DVB with either phenyl 4-vinylbenzenesulfonate (PVBS) or 4-vinylbenzyl amine hydrochloride (VBAH) functional monomers together with subsequent hydrolyzation or alkaline treatment. The bi-functional polymeric materials were utilized as a synergistic catalytic system for one-pot cascade reactions including deacetalization-Henry condensation reaction, deacetalization-Knoevenagel condensation reaction and the transformation of 3,4-dihydropyran derivatives to α-ester cyclohexenone compounds. The crosslinked polymeric frameworks effectively isolated sulfonic acid and primary amine groups to ensure their roles as both acid and base catalyst simultaneously in a one-pot system. The hierarchical porosity of a physically mixed acid/base co-catalyst system provided the possibility for the multi-step transformation of more complex substrates.
- Bian, Guomin,Huang, Xianpei,Liu, Fuyao,Qi, Yonglin,Sun, Zunming,Yang, Xinlin,Yang, Xinyue,Zhang, Mengmeng,Zhang, Wangqing
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p. 9546 - 9556
(2020/06/17)
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- Cascade reaction synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof
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The invention discloses a cascade reaction synthesis method of 2-(phenylmethylene)malononitrile or a derivative thereof. According to the invention, a dendritic acid-alkali catalyst based on cross-linked polystyrene is synthesized, and 2-(phenylmethylene) malononitrile or a derivative thereof is synthesized in batches by successfully applying a cascade reaction into fluid chemistry, so that the method of the invention has advantages of substantially reduced, yield increase and no separation process of a catalyst and a product compared with the traditional test tube reaction.
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Paragraph 0038-0042
(2020/03/12)
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- Highly Active Bisamino Functionalized Zr(IV)-UiO-67 Metal-Organic Framework for Cascade Catalysis
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This work reports the synthesis and characterization of Zr(IV)-based UiO-67-(NH2)2 (called 1) metal-organic framework. Activated 1 (named 1') was shown to be an efficient tandem catalyst in the conversion of benzaldehydedimethyl acet
- Das, Aniruddha,Anbu, Nagaraj,Mostakim,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
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supporting information
p. 2830 - 2834
(2020/07/04)
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- A facile, efficient and solvent-free titanium (IV) ethoxide catalysed knoevenagel condensation of aldehydes and active methylenes
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Titanium ethoxide has been employed as a novel and efficient reagent for the Knoevenagel condensation of aldehydes with active methylenes such as diethyl malonate and ethyl cyanoacetate under solvent free conditions to afford substituted olefins in high to excellent yields. The reaction is suitable for a variety of aromatic, aliphatic and heteroaromatic aldehydes with various active methylenes. Parallel to this, microwave irradiation has been utilized to achieve improved reaction rates and enhanced yields. Herein, we illustrated a convenient method for the preparation of α,β-unsaturated compounds using both conventional and microwave irradiation methods. An efficient and solvent free Knoevenagel condensation between aldehydes and active methylenes was developed using titanium ethoxide. The procedure proved to be successful with a wide range of substrates such as aromatic, aliphatic and heterocyclic aldehydes and various active methylenes to afford substituted olefins. The reaction was also carried out under microwave irradiation to accomplish the corresponding olefins with improved reaction rates, yields and cleaner reaction profiles.We have developed an efficient and novel methodology for the synthesis of olefinic compounds by Knoevenagel condensation under solvent-free conditions using titanium ethoxide, for the first time, as a reagent as well as a solvent. This method is appropriate for the synthesis of a variety of aromatic aldehydes containing various electron-donating and withdrawing groups, aliphatic and heteroaromatic aldehydes. The significant advantages offered by this methodology could be applied to various active methylenes in order to offer the corresponding Knoevenagel products. Thus, we believe that this method delivers high conversions, cleaner reaction profiles under solvent-free reaction conditions and shorter reaction times, all of which make it a very useful and attractive approach for the preparation of a wide range of substituted olefins.
- Ramaiah, Manjunatha M.,Shivananju, Nanjunda Swamy,Shubha, Priya Babu
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p. 107 - 115
(2020/02/04)
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- The Modified Clay as a New and Eco-Friendly Catalyst for the Knoevenagel Reaction
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Abstract: This work aims the synthesis of substituted alkenes via Knoevenagel condensation using the clay collected from the Agadir region and modified by KF as a heterogeneous catalyst (KF-modified clay). In this context, the influence of various paramet
- Bentahar, S.,Dbik, A.,Khomri, M. El,Lacherai, A.,Messaoudi, N. El,Sabour, A.,Taleb, M. Ait
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p. 1438 - 1444
(2020/10/29)
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- Tandem synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof
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A tandem synthesis method of 2-(phenylmethylene)malononitrile or a derivative thereof is disclosed. The general structural formula of the 2-(phenylmethylene)malononitrile or a derivative thereof is shown in the description, wherein R1 is hydrogen, p-methoxy, 2-bromo, 3-bromo or 4-bromo, and R2 is a cyano or ester group. A chloromethylated polystyrene microsphere acid-base functionalized catalyst is synthesized, a tandem reaction is successfully applied to the flow chemistry, and the 2-(phenylmethylene)malononitrile or a derivative thereof is synthesized in a gram scale. Compared with traditional test tube reactions, the method greatly reduces the reaction time, improves the yield and product purity, and avoids a step of separating a product from the catalyst.
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Paragraph 0034-0038
(2019/10/01)
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- Molybdenum oxide nanoparticles as recyclable heterogeneous catalyst for synthesis of arylidene ethyl cyanoacetates
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This work reports an adapted route to the highly efficient synthesis of arylidene ethyl cyanoacetate derivatives in the presence of catalytic amounts of molybdenum oxide nanoparticles (MoO3 NPs) under green conditions at ambient temperature. From the reaction, a wide range of novel arylidene ethyl cyanoacetates was successfully synthesized with high yields from the Knoevenagel condensation reaction between various aryl aldehydes and ethyl cyanoacetate in the presence of MoO3 nanoparticles. The capability of catalyst to separate from the reaction mixture and then reuse is another advantage of this reaction. Furthermore, obtained products belong to analogous of organic compounds that have shown biological activity, and can be used pharmaceutics.
- Pourshojaei, Yaghoub,Eskandari, Khalil,Elhami, Elaheh,Asadipour, Ali
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p. 5965 - 5973
(2019/06/14)
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- Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature
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Abstract: Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with malononitrile and ethyl cyanoacetate. The reaction proceeds at room temperature without using any organic solvent and is very fast with good to excellent yield. Additionally, the catalyst is easily separable and recyclable without loss of activity. Graphic Abstract: [Figure not available: see fulltext.].
- Burate, Pralhad A.,Javle, Balasaheb R.,Desale, Pranjal H.,Kinage, Anil K.
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p. 2368 - 2375
(2019/06/17)
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- The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions
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The Knoevenagel condensation between active methylene compounds and aromatic carobonyl compounds has been developed using quinine as an organocatalyst to afford various electrophilic alkenes in excellent yields (up to 90%). In the presence of a catalytic amount of quinine (15 mol%), the reaction proceeded at room temperature (RT) under solvent-free conditions. In this green approach, the organocatalyst was recovered and recycled for up to four cycles without appreciable loss of activity.
- Jain, Kavita,Chaudhuri, Saikat,Pal, Kuntal,Das, Kalpataru
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supporting information
p. 1299 - 1304
(2019/01/21)
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- A double basic Sr-amino containing MOF as a highly stable heterogeneous catalyst
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A novel metal-organic framework (MOF) based on strontium alkaline-earth metal and 2-amino-1,4-benzenedicarboxylic acid (NH2-bdc) has been developed. This material is formed by a linear succession of face-sharing strontium polyhedra bridged by a
- Leo, Pedro,Orcajo, Gisela,Briones, David,Rodríguez-Diéguez, Antonio,Choquesillo-Lazarte, Duane,Calleja, Guillermo,Martínez, Fernando
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p. 11556 - 11564
(2019/08/07)
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- Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes
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A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 molpercent PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
- Mangaonkar, Saeesh R.,Singh, Fateh V.
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p. 4473 - 4486
(2019/11/21)
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- Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)
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Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.
- Rupanawar, Bapurao D.,Veetil, Sruthi M.,Suryavanshi, Gurunath
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p. 6232 - 6239
(2019/11/05)
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- Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction
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A new enzymatic protocol based on lipase-catalyzed cascade toward (E)-α,β-unsaturated carboxylic esters is presented. The proposed methodology consists of elementary organic processes starting from acetals and cyanoacetic acid leading to the formation of desired products in a cascade sequence. The combination of enzyme promiscuous abilities gives a new opportunity to synthesize complex molecules in the one-pot procedure. Results of studies on the influence of an enzyme type, solvent, and temperature on the cascade reaction course are reported. The presented methodology provides meaningful qualities such as significantly simplified process, excellent E-selectivity of obtained products and recycling of a biocatalyst.
- Wilk, Monika,Trzepizur, Damian,Koszelewski, Dominik,Brodzka, Anna,Ostaszewski, Ryszard
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- Compartmentalization of Incompatible Polymers within Metal–Organic Frameworks towards Homogenization of Heterogeneous Hybrid Catalysts for Tandem Reactions
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New catalytic systems that contain incompatible catalytic sites were constructed by the in situ polymerization of acidic and basic polymers into metal–organic frameworks, which resulted in highly porous, recyclable, and durable catalytic composites with excellent compartmentalization, so that opposing agents were spatially isolated. These synthesized hybrid catalysts exhibited excellent catalytic activity for one-pot “wolf and lamb” reactions (deacetalization/Knoevenagel or Henry), which was attributed to their unique characteristic of having a locally homogeneous, but globally heterogeneous, structure.
- Zhao, Jin-Hao,Yang, Yong,Che, Jin-Xin,Zuo, Jun,Li, Xiao-Hua,Hu, Yong-Zhou,Dong, Xiao-Wu,Gao, Liang,Liu, Xin-Yuan
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supporting information
p. 9903 - 9909
(2018/07/25)
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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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- Ultrasound-assisted rapid synthesis of β-cyanoepoxides using hypervalent iodine reagents
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An elegant approach for the rapid synthesis of β-cyanoepoxides 3 by the epoxidation of β-cyanostyrenes 1 with PIDA 2a is described. The epoxidation of β-cyanostyrenes 1 was performed with 1.2 equiv. of PIDA 2a in MeCN-H2O (1:1) at room temperature in ultrasonic bath. The epoxidation reactions were completed in short reaction time and β-cyanoepoxides 3 were isolated in 69–94% yields.
- Singh, Fateh V.,Mangaonkar, Saeesh R.,Kole, Priyanka B.
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supporting information
p. 2169 - 2176
(2018/07/21)
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- 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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- Knoevenagel condensation catalyzed by novel Nmm-based ionic liquids in water
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A series of novel N-methyl morpholine (Nmm) based ionic liquids with 1,2-propanediol group were synthesized and used as catalysts for Knoevenagel condensation at room temperature in water. Under the effect of the catalyst, various aldehydes or aliphatic ketones could react with a wide range of activated methylene compounds well, including malononitrile, alkyl cyanoacetate, cyanoacetamide, β-diketone, barbituric acid, 2-arylacetonitrile and thiazolidinedione. Furthermore, most of the products could be separated just by filtrating and washing with water. Additionally, the catalyst is recyclable and applicable for the large-scale synthesis.
- Xu, Hao,Pan, Liyang,Fang, Xiaomin,Liu, Baoying,Zhang, Wenkai,Lu, Minghua,Xu, Yuanqing,Ding, Tao,Chang, Haibo
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supporting information
p. 2360 - 2365
(2017/05/29)
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- Microwave assisted urea-acetic acid catalyzed knoevenagel condensation of ethyl cyanoacetate and 1,3-Thiazolidine-2,4-dione with aromatic aldehydes under solvent free condition
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Knoevengel condensation reaction of various aromatic aldehydes with ethyl cyanoacetate and 1,3-thiazolidinone-2,4-diones catalyzed by urea-acetic acid under solvent free condition where olefinic products were obtained in high yield within short reaction time.
- Tryambake, Pravin. T.
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p. 2401 - 2405
(2017/10/31)
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- Covalently anchored tertiary amine functionalized ionic liquid on silica coated nano-Fe3O4 as a novel, efficient and magnetically recoverable catalyst for the unsymmetrical Hantzsch reaction and Knoevenagel condensation
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A novel magnetic nanoparticle supported basic ionic liquid was successfully prepared by covalently anchoring 1-(2′-piperidyl)ethyl-3-(3-propyltriethoxysilane)imidazolium chloride onto the surface of silica-coated Fe3O4 nanoparticles, and characterized by FT-IR, TEM, XRD, TGA, VSM and elemental analysis. The obtained supported ionic liquid was certified as a versatile and robust catalyst for the unsymmetrical Hantzsch reaction and Knoevenagel condensation under solvent-free conditions. Furthermore, the catalyst could be conveniently recovered by an external magnet and reused six times without significant loss of catalytic activity.
- Zhang, Qiang,Ma, Xiao-Ming,Wei, Huai-Xin,Zhao, Xin,Luo, Jun
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p. 53861 - 53870
(2017/12/05)
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- A mechanistic study of the Knoevenagel condensation reaction: New insights into the influence of acid and base properties of mixed metal oxide catalysts on the catalytic activity
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A Knoevenagel condensation reaction between benzaldehyde and ethyl cyanoacetate was performed in the liquid phase under mild and solventless conditions using a series of catalysts modified by impregnating magnesium and barium cations on different supports
- Li, Jerry P. H,Adesina, Adesoji A,Kennedy, Eric M,Stockenhuber, Michael
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p. 26630 - 26644
(2017/10/19)
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- Development of the First Two-Pore Domain Potassium Channel TWIK-Related K+ Channel 1-Selective Agonist Possessing in Vivo Antinociceptive Activity
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The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs, suggesting that activation of TREK-1 could result in pain inhibition. Here, we report the synthesis of a series of substituted acrylic acids (1-54) based on our previous work with caffeate esters. The analogues were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid-induced writhing and hot plate assays), leading to the identification of a series of novel molecules able to activate TREK-1 and displaying potent antinociceptive activity in vivo. Furyl analogue 36 is the most promising of the series.
- Vivier, Delphine,Soussia, Ismail Ben,Rodrigues, Nuno,Lolignier, Stéphane,Devilliers, Ma?ly,Chatelain, Franck C.,Prival, Laetitia,Chapuy, Eric,Bourdier, Geoffrey,Bennis, Khalil,Lesage, Florian,Eschalier, Alain,Busserolles, Jér?me,Ducki, Sylvie
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supporting information
p. 1076 - 1088
(2017/02/19)
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- Amide-Group-Directed Protonolysis of Cyclopropane: An Approach to 2,2-Disubstituted Pyrrolidines
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Regioselective protonolytic C-C bond cleavage of acylated aminomethyl cyclopropanes can be achieved using trifluoroacetic acid. The intermediate tertiary carbenium ion undergoes an intramolecular amination to give 2,2-substituted pyrrolidines. The strength of the acid and the amine substituent are important factors to achieve high regioselectivity, suggesting intramolecular proton transfer from the protonated amide function. Preliminary mechanistic studies revealed that cyclopropane cleavage proceeds with retention of configuration at the carbon to which the proton is attached. This observation is consistent with the "edge" protonation trajectory of the C-C bond.
- Skvorcova, Marija,Jirgensons, Aigars
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supporting information
p. 2478 - 2481
(2017/05/24)
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- Structural diversity and catalytic properties of five Co2(COO)4 cluster-based coordination polymers modified with R-isophthalic acid (R = H, NO2, CH3, OH and :tBu)
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The self-assembly of 5-substituted isophthalic acid (R-H2BDC, R = H, -NO2, -CH3, -OH and -tBu), CoII ions and 2,4,6-tris(4-pyridyl)-1,3,5-triazine (TPT) under solvothermal conditions yielded five Co-based coordination polymers (CPs): {[Co(BDC)(TPT)]·0.5(H2O)}n (CP1), {[Co(NO2-BDC)(TPT)]·H2O}n (CP2), {[Co(CH3-BDC)(TPT)]·0.5H2O}n (CP3), {[Co(HO-BDC)(TPT)]·0.5H2O}n (CP4), and {[Co(tBu-BDC)(TPT)2/3]·(CH3CH2OH)(H2O)}n (CP5) (H2BDC = isophthalic acid, NO2-BDC = 5-nitroisophthalic acid, CH3-BDC = 5-methylisophthalic acid, OH-BDC = 5-hydroxyisophthalic acid and tBu-BDC = 5-tert-butylisophthalic acid). All compounds comprise Co2(COO)4 binuclear units, which are connected via a combination of R-H2BDC and TPT ligands. In CP1, the binuclear Co2(COO)4 units are bridged into 1D chains extending along the [1 1 0] and [-1 1 0] directions, which are further interlinked by TPT ligands into a 3D network with CdS net topology. CP2, CP3 and CP4 are iso-structural and all exhibit 3D frameworks with pcu (α-Po) topology. In CP5, the Co2(COO)4 units are firstly linked into a 3D NbO net viatBu-BDC ligands, which are further accommodated by size-matching trigonal TPT ligands into a novel (3,8)-connected 3D net. Catalytic measurements show that CP2 and CP3 are good catalysts for the Knoevenagel condensation reaction of benzaldehyde with ethyl cyanoacetate, exhibiting conversions of 91.3% and 96.6% in 120 min, respectively, compared with the other present compounds. In addition, CP2 and CP5 exhibit highly efficient catalytic properties for the selective epoxidation of styrene.
- Zhang, Jian-Yong,Shi, Jun-Xia,Cui, Peng-Hui,Yao, Zi-Jian,Deng, Wei
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p. 5038 - 5047
(2017/09/11)
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- INHIBITORS OF BACTERIAL GLYCOSYL TRANSFERASES
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Described herein are compounds of Formula (I'), Formula (IA), Formulae (I)-(VII), pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrug sthereof. The invention also provides pharmaceutical compositions of the compounds for human and veterinary use. Compounds of the present invention are useful for inhibiting bacterial growth and therefore are useful in treating and/or preventing bacterial infections. Methods of using the compounds for treating and/or preventing a bacterial infection in a subject are also described.
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Paragraph 00727; 00728-00729
(2016/12/22)
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- Three-Dimensional Covalent Organic Frameworks with Dual Linkages for Bifunctional Cascade Catalysis
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Covalent organic frameworks (COFs) are an emerging class of porous crystalline polymers with broad potential applications. So far, the availability of three-dimensional (3D) COFs is limited and more importantly only one type of covalent bond has been successful used for 3D COF materials. Here, we report a new synthetic strategy based on dual linkages that leads to 3D COFs. The obtained 3D COFs show high specific surface areas and large gas uptake capacities, which makes them the top COF material for gas uptake. Furthermore, we demonstrate that the new 3D COFs comprise both acidic and basic sites, and act as excellent bifunctional catalysts for one-pot cascade reactions. The new synthetic strategy provides not only a general and versatile approach to synthesize 3D COFs with sophisticated structures but also expands the potential applications of this promising class of porous materials.
- Li, Hui,Pan, Qinying,Ma, Yunchao,Guan, Xinyu,Xue, Ming,Fang, Qianrong,Yan, Yushan,Valtchev, Valentin,Qiu, Shilun
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p. 14783 - 14788
(2016/11/18)
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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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- A simple and efficient procedure for the Knoevenagel condensation catalyzed by [MeHMTA]BF4 ionic liquid
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Hexamethylenetetramine-based ionic liquid, 1-methylhexamethylenetetraminium tetrafluoroborate, has been used as a catalyst for a simple and efficient method for Knoevenagel condensation of active methylene compounds and various carbonyl compounds affordin
- Keithellakpam, Sanjoy,Moirangthem, Nimalini,Laitonjam, Warjeet S.
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p. 1157 - 1161
(2015/09/28)
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- Green condensation reaction of aromatic aldehydes with active methylene compounds catalyzed by anion-exchange resin under ultrasound irradiation
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To realize a practical and green chemistry, two important challenges need to be addressed, namely the effective process for the activation of reaction and efficient, eco-friendly and robust chemical methods for the reaction conversion to target products v
- Ammar, Hafedh Belhadj,Chtourou, Manef,Frikha, Mohamed Hédi,Trabelsi, Mahmoud
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p. 559 - 564
(2014/11/08)
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- Ultrasound-promoted knoevenagel condensation catalyzed by KF-clinoptilolite
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Potassium fluoride-clinoptilolite, which is prepared from commercially available and cheap starting materials, was used as an efficient and recyclable catalyst for Knoevenagel condensation of aromatic aldehydes with active methylene compounds under ultras
- Keipour, Hoda,Hosseini, Abolfazl,Khalilzadeh, Mohammad A.,Ollevier, Thierry
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p. 645 - 650
(2015/11/09)
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- Fluorous bispidine: A bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water
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Fluorous bispidine-type ligands have been developed to facilitate its recovery and reusability and to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/Knoevenagel condensation in water under mild conditions. Application of the fluorous ligand was also extended to the surfactant-free copper-catalyzed allylic and benzylic sp3 C-H oxidation reaction in water. The fluorous ligands could be recovered using F-SPE with recovery ranging from 91-97% and could be reused five times with little loss of activity.
- Ang, Wei Jie,Chng, Yong Sheng,Lam, Yulin
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p. 81415 - 81428
(2015/10/06)
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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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- Straightforward syntheses of nitriles, acrylates, and acrylamides in aqueous propan-1,2-diol: A catalyst free and waste free methodology
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A mild, elegant, catalyst free, and waste free methodology has been developed for the clear-cut synthesis of a diverse range of nitriles, acrylates, and acrylamides in good to excellent yields using aqueous propan-1,2-diol, a green reaction medium, at ambient temperature. Operational simplicity and recyclability of the reaction medium are added advantages of the methodology.
- Jayalakshmi, Lakshmi Narayanan,Karuppasamy, Ayyanar,Stalindurai, Kesavan,Sivaramakarthikeyan, Ramar,Devadoss, Vellasamy,Ramalingan, Chennan
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supporting information
p. 4207 - 4210
(2015/06/22)
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- Amine-modified hierarchically structured zeolites as acid-base bi-functional catalysts for one-pot deacetalization-Knoevenagel cascade reaction
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Hierarchically structured zeolites (HSZs) with crystalline microporous frameworks and penetrating mesoporosity have been developed and used as efficient solid acid catalysts in many chemical processes, especially when bulky molecules are involved. Herein,
- Ge, Tongguang,Hua, Zile,Zhu, Yan,Song, Yudian,Tao, Guiju,Zhou, Xiaoxia,Chen, Lisong,Ren, Wenchao,Yao, Heliang,Shi, Jianlin
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p. 64871 - 64876
(2015/04/27)
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- One-pot tandem catalytic synthesis of α, β-unsaturated nitriles from alcohol with nitriles in aqueous phase
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Pd1-Au1 bimetal catalysts supported on basic layered double hydroxide (LDH) have been prepared conveniently with surface impregnation methods and structurally characterized by XRD, TEM and XPS. The nanoparticles were highly dispersed on LDH with an average size of 2.08 ± 0.3 nm and showed a strong cooperative effect between Au and Pd for the step of the alcohol oxidation. Moreover, the present hydrotalcite-supported bimetal catalysts can catalyze efficiently one-pot α-arylation reactions of nitriles with various alcohols in aqueous phase through tandem reactions. The bimetal catalyst has been extended for a broad substrate scope and recycled for at least 4 times.
- Chen, Chen,Yang, Hanmin,Chen, Jizhong,Zhang, Ran,Guo, Li,Gan, Huimei,Song, Baoning,Zhu, Wenwen,Hua, Li,Hou, Zhenshan
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- Aqueous DABCO, an efficient medium for rapid organocatalyzed Knoevenagel condensation and the Gewald reaction
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In the presence of water and 1,4-diazabicyclo[2.2.2]octane, several aldehydes and cyclic ketones underwent efficient Knoevenagel condensation with malononitrile and ethyl cyanoacetate to produce the respective α.β-unsaturated systems within fairly short time periods. As a result, high yields of conjugated products were easily obtained. Products could be engaged in a Gewald reaction, either stepwise or in situ, to produce efficiently their respective 2-aminothiophenes within 4-7 h. TUeBITAK.
- Abaee, Mohammad Saeed,Cheraghi, Somayeh
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p. 650 - 660
(2014/07/07)
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- Graphene based material as a base catalyst for solvent free Aldol condensation and Knoevenagel reaction at room temperature
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Graphene oxide (GO) acts as a highly active heterogeneous base catalyst for a wide variety of reactions. Here we have described the catalytic activities of GO in the condensation reaction of various substituted benzaldehydes with acetophenone (aldol condensation) and with active methylene compound malononitrile (Knoevenagel reaction) at room temperature under solvent free condition. GO is characterized by powder X-ray diffraction (XRD), UV-visible spectra, Fourier transform infrared spectroscopy (FT-IR) and AFM. The experimental results showed that the GO had higher catalytic activity and it can be recycled without significant loss of its activity.
- Islam, Sk Manirul,Roy, Anupam Singha,Dey, Ram Chandra,Paul, Sumantra
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- Reduced graphene oxide supported piperazine in aminocatalysis
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Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions. This journal is the Partner Organisations 2014.
- Rodrigo, Eduardo,García Alcubilla, Beatriz,Sainz, Raquel,Fierro, J. L. García,Ferritto, Rafael,Cid, M. Belén
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supporting information
p. 6270 - 6273
(2014/06/09)
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- Aminated poly(vinyl chloride): An efficient green catalyst for Knoevenagel condensation reactions
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Commercially available poly(vinyl chloride) have been modified with ethylene diamine to give a highly efficient reusable organocatalyst for Knoevenagel condensation in water as well as under solvent-less conditions. The reaction proceeds with high yield a
- Rajesh Krishnan,Sree Niveditha,Sreekumar
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p. 428 - 431
(2013/05/08)
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- One-pot multifunctional catalysis with NNN-Pincer Zr-MOF: Zr base catalyzed condensation with Rh-catalyzed hydrogenation
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We describe the postsynthetic modification of Zr-based metal organic frameworks (MOFs) containing chiral NNN-pincer ligands based on aminopyridineimines, as well as the subsequent formation of (NNN)-M-Zr-MOF complexes (M=Rh, Ir). With these new multifunct
- Rasero-Almansa, Antonia M.,Corma, Avelino,Iglesias, Marta,Sánchez, Félix
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p. 3092 - 3100
(2013/10/21)
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- Immobilization of L-Lysine on zeolite 4A as an organic-inorganic composite basic catalyst for synthesis of α,β-unsaturated carbonyl compounds under mild conditions
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Lysine (Lys) immobilized on zeolite 4A was prepared by a simple adsorption method. The physical and chemical properties of Lys/zeolite 4A were investigated by X-ray diffraction (XRD), FT-IR, Brunauer-Emmett-Teller (BET), scanning electron microscopy (SEM)
- Zamani, Farzad,Rezapour, Mehdi,Kianpour, Sahar
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p. 2367 - 2374
(2013/09/24)
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