- Reversible Phase Transfer of Carbon Dots between an Organic Phase and Aqueous Solution Triggered by CO2
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Carbon dots (CDs) have attracted increasing attention in applications such as bio-imaging, sensors, catalysis, and drug delivery. However, unlike metallic and semiconductor nanoparticles, the transfer of CDs between polar and non-polar phases is little un
- Pei, Xiaoyan,Xiong, Dazhen,Wang, Huiyong,Gao, Shuaiqi,Zhang, Xinying,Zhang, Suojiang,Wang, Jianji
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Read Online
- Effecting structural diversity in a series of Co(ii)-organic frameworks by the interplay between rigidity of a dicarboxylate and flexibility of bis(tridentate) spanning ligands
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In a one-pot self-assembly reaction of Co(OAc)2·4H2O, thiophene-2,5-dicarboxylic acid (H2tdc) and four different bis(tridentate) polypyridyl spanning ligands under ambient conditions, a series of structurally diverse metal-organic frameworks has been synt
- Gogia, Alisha,Khullar, Sadhika,Laha, Biswajit,Mandal, Sanjay K.
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Read Online
- First organocatalytic asymmetric synthesis of 1-Benzamido-1,4-Dihydropyridine Derivatives
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Preliminary results concerning the first asymmetric synthesis of highly functionalized 1-benzamido-1,4-dihydropyridine derivatives via the reaction of hydrazones with alkylidenemalononitriles in the presence of β-isocupreidine catalyst are reported. The m
- Auria-Luna, Fernando,Marqués-López, Eugenia,Herrera, Raquel P.
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Read Online
- Synthesis, molecular docking, and in silico ADME prediction of some fused pyrazolo[1,5-a]pyrimidine and pyrazole derivatives as potential antimicrobial agents
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Twenty compounds of pyrazolo[1,5-a]pyrimidines 14a–j and pyrazole derivatives as Schiff bases 16a–j have been synthesized by the reaction of 5-amino-pyrazole derivatives 9a, b with 2-(arylidene)malononitriles 10a–e or various aldehydes 15a–e, respectively
- Hassan, Ashraf S.,Morsy, Nesrin M.,Awad, Hassan M.,Ragab, Ahmed
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p. 521 - 545
(2021/07/06)
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- Effect of supramolecular polymeric aggregation in room temperature ionic liquids (RTILs) on catalytic activity in the synthesis of 4H-chromene derivatives and Knoevenagel condensation
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RTILs exhibit supramolecular self-assembled polymeric aggregation due to noncovalent interactions. The influence of the aggregation behaviour of RTILs on catalytic activity is evident but still poorly understood. The present work focuses on establishing a
- Muhammad, Shoaib,Ali, Firdous Imran,Javed, Muhammad Naveed,Wasim, Agha Arsalan,Bari, Ahmed,Rafique, Faisal,Ilyas, Muhammad Amjad,Riaz, Kashif,Mahmood, Syed Junaid,Ahmed, Amir,Hashmi, Imran Ali
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- Introduction of succinimide as a green and sustainable organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b] pyran derivatives
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Aim and Objective: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives
- Hassanzadeh, Fariba,Shirini, Farhad,Mamaghani, Manouchehr,Daneshvar, Nader
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p. 155 - 163
(2021/03/23)
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- Development of an efficient, one-pot, multicomponent protocol for synthesis of 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives
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A one-pot quick and efficient multicomponent reaction has been developed for the synthesis of a new series of functionalized 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives using 30 mol% ammonium acetate in ethanol as solvent. This economical protocol
- Tabassum, Rukhsana,Ashfaq, Muhammad,Oku, Hiroyuki
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p. 534 - 547
(2020/12/04)
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- Phosphine-Catalyzed (4 + 2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives
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The δ-sulfonamido-substituted enones were employed as phosphine acceptor in phosphine-catalyzed (4 + 2) annulation of 1,1-dicyanoalkenes. They served as a four-membered synthon to react with 1,1-dicyanoalkenes under mild reaction conditions, producing pip
- Liu, Min,Zhou, Leijie,Shi, Wangyu,Hu, Yimin,Liao, Jianning,Duan, Zeqing,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
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supporting information
p. 7703 - 7707
(2021/10/20)
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- Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
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Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
- Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
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- Introduction of a new bis-derivative of succinimide (Bis-Su) as a sustainable and efficient basic organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives under green conditions
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Organo-catalysts have been under great consideration for many years because of their performance and selectivity in the reactions. In this work, a new bis-succinimide (Bis-Su) compound is prepared, identified and used as a green and efficient basic organo
- Hassanzadeh, Fariba,Daneshvar, Nader,Shirini, Farhad,Mamaghani, Manouchehr
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p. 4971 - 4984
(2020/09/02)
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- Hydroquinone and benzoquinone-catalyzed aqueous Knoevenagel condensation
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A Knoevenagel condensation of various aldehydes with malononitrile effectively proceeded in the presence of hydroquinone/benzoquinone mixed catalysts at room temperature in H2O. Furthermore, γ-deuterium-labeled α,β-unsaturated nitrile derivatives were als
- Koyama, Kaho,Kuwata, Marina,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya,Yamada, Tsuyoshi
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supporting information
p. 6594 - 6597
(2020/09/21)
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- Amine-functionalized hollow mesoporous nano-bowl with bulky acid-imprinted free space around base sites and DMF-annealed mesoporous channels as an efficient solid base catalyst
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Tailoring free spaces around catalytic sites and constructing inter-connected channels between them are highly attractive for achieving easy accessibility of reactants to catalytic sites. In this study, a strategy for constructing free space around base s
- Li, Shan,Ma, Xuebing,Wei, Shuai,Zhang, Jianing,Zhang, Li
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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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- 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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- Chiral-at-Metal Rh(III) Complex Catalyzed Cascade Reduction-Michael Addition Reaction
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An enantioselective three-component cascade reduction-Michael addition reaction catalyzed by chiral-at-metal Rh(III) complexes has been developed. With a Hantzsch ester as the hydride source, a number of malononitrile derivatives were prepared in good yie
- Wan, Qian,Li, Shiwu,Kang, Qiang,Yuan, Yaofeng,Du, Yu
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p. 15201 - 15211
(2019/11/19)
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- Synthesis and anticholinesterase activity of novel non-hepatotoxic naphthyridine-11-amine derivatives
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Abstract: In the present study, 14 novel naphthyridine-11-amine derivatives were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 12-(4-Fluorophenyl)-1,2,3,4,7,8,9,10-octahydrodibenz
- Zengin Kurt, Belma
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p. 625 - 638
(2018/12/11)
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- Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides
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A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.
- Zhang, Dapeng,Lian, Mingming,Liu, Jia,Tang, Shukun,Liu, Guangzhi,Ma, Cunfei,Meng, Qingwei,Peng, Haisheng,Zhu, Daling
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supporting information
p. 2597 - 2601
(2019/04/17)
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- Design and Construction of a Chiral Cd(II)-MOF from Achiral Precursors: Synthesis, Crystal Structure and Catalytic Activity toward C-C and C-N Bond Forming Reactions
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Using achiral components, a V-shaped dicarboxylic acid (H2L) and a conformationally flexible bidentate linker (bpp), a thermally stable chiral metal organic framework {[Cd(bpp)(L)(H2O)]·DMF}n (1), where H2L = 4,
- Gupta, Vijay,Mandal, Sanjay K.
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p. 3219 - 3226
(2019/03/28)
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- Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
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A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit
- Liu, Yingtian,Dang, Xinxin,He, Yu,Bai, Hudong,Chen, Xuehong,Li, Jun-Long,Fan, Junting,Jiang, Hezhong,Li, Jiahong
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p. 662 - 671
(2019/02/20)
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- Access to thiomorpholin-3-one derivatives: [3 + 3]-cycloadditions of α-chlorohydroxamates and 1,4-dithiane-2,5-diol
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A protocol of [3 + 3]-cycloaddition was proposed for the synthesis of 2H-1,4-thiazin-3(4H)-ones and thiomorpholine-3,5-diones from α-chlorohydroxamates and 1,4-dithiane-2,5-diol. This direct and practical method provides a novel and rapid approach for the
- He, Zhao-Lin,Chen, Yi,Wang, Xiaohua,Ni, Mingwang,Wang, Gang
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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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p. 3059 - 3067
(2018/03/06)
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- Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
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Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
- Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
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p. 181 - 199
(2018/03/13)
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- Polyoxoniobates as a superior Lewis base efficiently catalyzed Knoevenagel condensation
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The outstanding basicity of negative charged Lindqvist type Polyoxoniobate K7HNb6O19·13H2O (Nb6) have been proved experimentally as well as by theoretical NBO calculations, the results insights high electron density on terminal and bridging oxygen atoms of niobate anion. The most negative Natural Bond Orbital charge (NBO) of oxygen in Nb6 is ?1.001, which is a much more negative value than those reported in other polyoxometalates, that corroborates its high basicity thus likely to be employed as a strong base catalyst. Experimental study suggests that Nb6 can efficiently catalyze Knoevenagel condensation of various carbonyl compounds with active methylene compounds neglecting the steric and electronic effect of aromatic aldehydes under mild conditions. Kinetic test shows that Knoevenagel condensation of benzaldehyde with ethyl cyanoacetate exhibits second-order kinetics in the presence of Nb6 and the calculated activation energy is 43.3 kJ mol?1. Meanwhile, a proper mechanism according to the NBO study speculates that the most negative charged terminal oxygens in Nb6 would be pivotal in this transformation.
- Xu, Qiaofei,Niu, Yanjun,Wang, Guan,Li, Yingguang,Zhao, Yuan,Singh, Vikram,Niu, Jingyang,Wang, Jingping
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- Water assisted and choline chloride-dimethylurea deep eutectic salts as catalyst towards the attractive reaction of indole, benzaldehyde, and malononitrile
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The condensation of indole, benzaldehyde, and malononitrile was relatively rigorous compared with other Yonemitsu type reaction. We described a strategy using catalytic amount of choline chloride-dimethylurea deep eutectic salts as cheap and safe accelerator. We also found that introducing right amount of water in reaction system was crucial. This method tolerates variations in all three components to get desired 3-substituted indoles in satisfactory yields.
- Ruan, Hongli,Lv, Yue,Yu, Shijun,Lv, Chengwei,An, Yue
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p. 1266 - 1274
(2018/08/06)
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- Coordination driven self-assembly of [2 + 2 + 2] molecular squares: Synthesis, crystal structures, catalytic and luminescence properties
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The one-pot self-assembly of three components (metal acetates as the metal precursor, the tridentate polypyridyl ligand, N,N′-bis(2-pyridylmethyl)-tert-butylamine (bpta), as a capping ligand and bent dicarboxylic acids, 4,4′-(dimethylsilanediyl)bis-benzoi
- Gupta, Vijay,Mandal, Sanjay K.
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p. 9742 - 9754
(2018/08/06)
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- Switchable oil-water phase separation of ionic liquid-based microemulsions by CO2
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Phase separation of microemulsions plays an important role in many applications such as oil recovery, nanomaterials synthesis, and chemical reactions. However, reversible switching from ionic liquid-based microemulsions to complete oil-water phase separation has not been reported so far. In this work, we developed a novel class of stimuli-responsive microemulsions composed of CO2-responsive ionic liquids, n-pentanol and water. The microstructures and phase behavior of the microemulsion systems before and after the bubbling of CO2 were investigated by electrical conductivity, dynamic light scattering, small-angle X-ray scattering, cryogenic transmission electron microscopy, and optical microscopy. It was found that these microemulsions could be reversibly switched from W/O monophase to complete oil-water phase separation upon alternate bubbling and removal of CO2 at atmospheric pressure. Furthermore, 13C NMR spectroscopy was used to understand the CO2-driven reversible phase separation of the microemulsions. The results suggest that the mechanism behind the reversible phase separation involved the reversible formation of bicarbonate and carbamate from the reaction between CO2 and the anions of the ionic liquids in the presence of water, which resulted in the increase of ionic strength (or vice versa) in the mixture. Using the microemulsions as microreactors, the phase separation protocol was applied in the Knoevenagel reaction for an efficient coupling of a chemical reaction, product separation, and recycling of the microemulsions.
- Pei, Xiaoyan,Xiong, Dazhen,Pei, Yuanchao,Wang, Huiyong,Wang, Jianji
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supporting information
p. 4236 - 4244
(2018/09/29)
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- Method for aldehyde Knoevenagel condensation reaction under conditions of no catalyst or solvent
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The invention discloses a method for an aldehyde Knoevenagel condensation reaction under conditions of no catalyst or solvent. In a glove box, aldehyde and malononitrile are sequentially added to a nuclear magnetic resonance tube, then, the glove box is m
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Paragraph 0064-0066
(2018/11/22)
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- Β-Cyclodextrin as a Biomimetic Catalyst for the Efficient Synthesis of 4-Oxo-pyrido[1,2-a] Pyrimidine-3-Carbonitrile in Aqueous Medium
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Abstract: Supramolecular β-cyclodextrin as a highly efficient, biodegradable, and reusable catalyst for the synthesis of 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonitrile derivatives (4a–s) is investigated via a cascade reaction of aldehydes, malanonitrile
- Ghorad, Akash,Mahalle, Sagar,Khillare, Lalit D.,Sangshetti, Jaiprakash N.,Bhosle, Manisha R.
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p. 640 - 648
(2017/03/08)
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- Effective and Green One-Pot Multicomponent Synthesis of Novel Derivatives of 4H-Pyrans in the Presence of Hexamethylenetetramine as Catalyst in Water Medium
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Hexamethylenetetramine catalyzes synthesis of new polyfunctionalized 4H-pyrans by the reaction of aromatic aldehyde, malononitrile, and β-keto esters via one-pot three-component procedure in water medium. Addition of reactants was performed by two methods
- Habibi, Maysam,Habibi, Azizollah,Hakimi Nasab, Saber,Dolati, Hadi,Mahdavi, Seyedeh Mahbobeh
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p. 1598 - 1603
(2017/03/27)
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- RETRACTED ARTICLE: Effective and Green One-Pot Multicomponent Synthesis of Novel Derivatives of 4H-Pyrans in the Presence of Hexamethylenetetramine as Catalyst in Water Medium
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Hexamethylenetetramine (HMTA) catalyzes synthesis of new polyfunctionalized 4H-pyrans by reaction of aromatic aldehyde, malononitrile, and β-keto esters via one-pot three-component procedure in water medium. Addition of reactants was performed by two meth
- Habibi, Maysam,Habibi, Azizollah,Hakimi Nasab, Saber,Dolati, Hadi,Mahdavi, Seyedeh Mahbobeh
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p. 1880 - 1886
(2017/05/29)
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- Metal-free visible light driven synthesis of tetrahydroquinoline derivatives utilizing Rose Bengal
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The visible-light driven reaction for the synthesis of tetrahydroquinoline derivatives via tandem radical cyclization of N,N-dimethylanilines with 2-benzylidenemalononitriles has been developed. Corresponding products were obtained with yields of up to 74
- Xin, Jing-Rui,Guo, Jun-Tao,Vigliaturo, Dominic,He, Yan-Hong,Guan, Zhi
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p. 4627 - 4633
(2017/07/11)
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- N-heterocyclic carbene-promoted [3+2] cycloaddition of allenyl sulfone and arylidenemalononitriles
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N-Heterocyclic carbenes promote the [3+2] cycloaddition of allenyl sulfone and arylidenemalononitriles, accompanied by 1,2-migration of the sulfonyl group. This reaction provides a new route to highly substituted cyclopentenes.
- Kuwano, Satoru,Masuda, Toshinobu,Yamaguchi, Koki,Arai, Takayoshi
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p. 232 - 242
(2017/07/28)
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- Electrochemical approach for synthesis of 3-substituted indole derivatives
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An efficient and economical method was developed for synthesis of 3-substituted indole by using electrochemically induced condensation of various aldehyde, indole and malononitrile.
- Singh, Vinay K.,Dubey, Rahul,Upadhyay, Abhishek,Sharma, Laxmi Kant,Singh, Rana Krishna Pal
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supporting information
p. 4227 - 4231
(2017/10/12)
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- An Efficient One-pot Three-component Process for Synthesis of Perfluoroalkylated Quinolizines
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A facile multi-component process for the synthesis of perfluoroalkylated quinolizine derivatives was achieved using various arylidenemalononitriles, pyridine, and methyl perfluoroalk-2-ynoates as starting materials. Moderate yields were obtained under mil
- Shen, Dandan,Xu, Yanjie,He, Dong,Han, Jing,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Cao, Weiguo
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p. 524 - 532
(2016/06/01)
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- Chemoenzymatic Synthesis of α-Cyano Epoxides by a Tandem-Knoevenagel-Epoxidation Reaction
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An efficient lipase-mediated synthesis of α-cyano epoxides through a tandem-Knoevenagel-epoxidation reaction was explored for the first time. This method provides a green, mild, and convenient route for the synthesis of α-cyano epoxides; moreover, the app
- Yang, Fengjuan,Zhang, Xiaowen,Li, Fengxi,Wang, Zhi,Wang, Lei
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supporting information
p. 1251 - 1254
(2016/03/16)
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- Visible light promoted synthesis of dihydropyrano[2,3-c] chromenes via a multicomponent-tandem strategy under solvent and catalyst free conditions
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The development of unique, mild and efficient one pot, multicomponent-tandem synthesis of highly functionalized dihydropyrano[2,3-c]chromenes under photochemical activation is reported. The key feature of the present work is the utilization of visible lig
- Tiwari, Jyoti,Saquib, Mohammad,Singh, Swastika,Tufail, Fatima,Singh, Mandavi,Singh, Jaya,Singh, Jagdamba
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supporting information
p. 3221 - 3231
(2016/06/13)
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- An efficient five-component synthesis of thioether containing dihydropyrano[2,3-c]pyrazoles: a green domino strategy
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An efficient route for the synthesis of novel thioether containing dihydropyrano[2,3-c]pyrazoles has been accomplished via a solvent-free, catalyst-free, one-pot, five component domino strategy. This synthetic approach offers several advantages such as an easy work-up, no need for purification techniques and a short reaction time with good atom economy and high yields of the products (81-86%).
- Ramesh, Vediyappan,Shanmugam, Sivakumar,Devi, Natarajan Savitha
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p. 9993 - 10001
(2016/12/07)
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- Iodine-mediated diastereoselective cyclopropanation of arylidene malononotriles by 2,6-dimethylquinoline
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A novel iodine-mediated reaction of 2,6-dimethylquinoline with Knoevenagel condensation products of malononitrile with benzaldehydes, leading to a facile, one-pot synthesis of 2-aryl-3-(6-methylquinolin-2-yl)cyclopropane-1,1-dicarbonitriles, in moderate t
- Yavari, Issa,Hosseinpour, Reza,Skoulika, Stavroula
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p. 380 - 384
(2015/02/19)
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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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supporting information
p. 14862 - 14870
(2015/10/20)
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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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- Solvent free highly dispersed zinc oxide within confined space of Al-Containing SBA-15 as an efficient catalyst for Knoevenagel Condensation
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A mesoporous silica-supported zinc oxide catalyst was successfully synthesized by directly grinding zinc nitrate into the as-prepared Al-Containing SBA-15 occluded with template and characterized by powder X-ray diffraction (XRD), BET nitrogen adsorption-
- Mahmoudi, Hesamaldin,Malakooti, Reihaneh
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p. 457 - 464
(2014/05/20)
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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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- A one-pot four-component synthesis of pyrrolo[1,2-a]quinolines
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A facile one-pot, four-component reaction for the synthesis of pyrrolo[1,2-a]quinolines is described. Knoevenagel condensation reaction of malononitrile and aromatic aldehydes gave 2-arylmethylidenemalononitriles which on treatment with quinoline and cycl
- Adib, Mehdi,Azimzadeh, Marjan,Rahimi-Nasrabadi, Mehdi,Zhu, Long-Guan
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p. 423 - 426
(2014/08/05)
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- Polystyrene-immobilized DABCO as a highly efficient and recyclable organocatalyst for the Knoevenagel condensation reaction
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Polystyrene-immobilized DABCO was used for the first time as a basic organocatalyst for carbon-carbon bond formation reactions. The supported catalyst could be used as a reusable catalyst in the Knoevenagel condensation of a wide range of aromatic/heterocyclic/α,β-unsaturated aldehydes and ketones with active methylene compounds. The reaction conditions are mild and the method is operationally simple. The reactions proceed in a short time period and with 100% selectivity. The catalyst could be easily separated from the reaction by filtration and recycled ten times without activity loss. Based on the catalyst, a continuous flow process was also developed.
- Xu, Da-Zhen,Shi, Sen,Wang, Yongmei
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p. 23075 - 23079
(2013/11/19)
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- Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions
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Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated α-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines and carbonyl compounds. It also enabled the development of one-pot synthesis of β-phosphonomalonates during the reaction of carbonyl compounds, malononitrile and phosphorus compounds. Excellent results were obtained in each case affording the corresponding organophosphorus adducts in good yields.
- Sharghi, Hashem,Ebrahimpourmoghaddam, Sakineh,Doroodmand, Mohammad Mahdi
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p. 4708 - 4724
(2013/06/26)
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- Facile synthesis of pure non-monoclinic zirconia nanoparticles and their catalytic activity investigations for Knoevenagel condensation
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Zirconia nanoparticles were synthesized by the non-hydrolytic thermal decomposition of zirconyl chloride octahydrate in the presence of oleylamine and oleic acid. The nanoparticles were characterized by XRD, HR-TEM and EDAX techniques. TEM observation con
- Malakooti, Reihaneh,Mahmoudi, Hesamaldin,Hosseinabadi, Rahele,Petrov, Srebri,Migliori, Andrea
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p. 22353 - 22359
(2013/11/06)
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- Electrocatalytic and chemical methods in MHIRC reactions: The first example of the multicomponent assembly of medicinally relevant spirocyclopropylbarbiturates from three different molecules
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Electrolysis of aldehydes, barbituric acids, and malononitrile in alcohol in an undivided cell in the presence of sodium bromide results in efficient MHIRC formation of the corresponding spirocyclopropylbarbiturates in 50-65% substance yield. The electroc
- Vereshchagin, Anatolii N.,Elinson, Michail N.,Dorofeeva, Evgeniya O.,Stepanov, Nikita O.,Zaimovskaya, Tatiana A.,Nikishin, Gennady I.
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p. 1945 - 1952
(2013/03/13)
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- Isocyanide-based multicomponent reactions: Catalyst-free stereoselective construction of polycyclic spiroindolines
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A novel catalyst-free one-pot tandem reaction for the stereoselective construction of polycyclic spiroindolines was developed. This method offers a straightforward access to structurally diverse polycyclic spiroindoline derivatives in high yields (up to 90%) with excellent levels of diastereoselectivity.
- Wang, Xiang,Wang, Shun-Yi,Ji, Shun-Jun
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supporting information
p. 1954 - 1957
(2013/05/23)
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- Solvent-free synthesis of novel 5-oxo-5H-chromeno[4,3-b]pyridine derivatives
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An efficient and simple method for the synthesis of new 5-oxo-5H-chromeno[4,3-b]pyridine derivatives via Michael addition of 4-aminocoumarin to arylidenemalononitrile for 20 min at 150 C without any solvent is proposed. The advantages of this procedure ar
- Motamedi
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p. 1839 - 1843
(2013/07/26)
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- Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase
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Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM).
- Khoobi, Mehdi,Alipour, Masoumeh,Moradi, Alireza,Sakhteman, Amirhossein,Nadri, Hamid,Razavi, Seyyede Faeze,Ghandi, Mehdi,Foroumadi, Alireza,Shafiee, Abbas
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p. 291 - 300
(2013/10/01)
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