- Succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano-pyrimidinones derivatives
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In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), a newly reported Br?nsted acidic ionic liquids is used as an efficient, homogeneous and reusable catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]-pyrimidine dione derivatives. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.
- Goli-Jolodar, Omid,Shirini, Farhad,Seddighi, Mohadeseh
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- 1-n-butyl-3-methylimmidazolium tetrafluoroborate-promoted green synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives
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The room temperature ionic liquid 1-n-butyl-3-methylimmidazolium tetra-fluoroborate ([bmim]BF4) was used to promote the synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives under the solid-state conditions of grinding or microwave irradiation without organic solvent. The yields were 77.9-96.2%. It is shown that the proposed method is fast, efficient, and environmentally benign. Copyright Taylor & Francis, Inc.
- Wang, Chun,Ma, Jing-Jun,Zhou, Xin,Zang, Xiao-Huan,Wang, Zhi,Gao, Yong-Jun,Cui, Peng-Lei
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- A simple method for knoevenagel condensation of α,β-conjugated and aromatic aldehydes with barbituric acid
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Several aromatic and α,β-conjugated aromatic aldehydes were condensed with barbituric acid in methanol solution in the absence of acid or base as a catalyst, affording 5-ylidenebarbituric acid derivatives in almost quantitative yields.
- Jursic
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- CoFe2O4 nanoparticles: An efficient heterogeneous magnetically separable catalyst for "click" synthesis of arylidene barbituric acid derivatives at room temperature
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A coprecipitation method was used to synthesize superparamagnetic CoFe 2O4 nanoparticles without using any capping agents/surfactants. The prepared nanoparticles were characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, a vibrating sample magnetometer (VSM), N2 adsorption and thermogravimetric/differential thermal analysis/differential thermal gravimetry techniques. The synthesized spinel CoFe2O4 nanoparticles had an average size of 2-8 nm with a high surface area (140.9 m2/g). The field-dependent magnetization, demonstrated by VSM and saturation magnetization, was found to be 1.77 emu/g. An efficient method was used for the synthesis of arylidene barbituric acid derivatives using CoFe2O4 magnetic nanoparticles as a magnetically separable and reusable catalyst in aqueous ethanol. The attractive features of this synthetic protocol were very short reaction time, high yields, high turnover frequency, simple work-up procedure, economy, a clean reaction methodology, and chemoselectivity, as well as provision of an ecofriendly and green synthesis.
- Rajput, Jaspreet Kaur,Kaur, Gagandeep
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- Preparation of benzylidene barbituric acids promoted by infrared irradiation in absence of solvent
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Several benzaldehydes were condensed with barbituric acid under infrared irradiation, in absence of solvent, affording the corresponding 5-benzylidene barbituric acids.
- Alcerreca, Guadalupe,Sanabria, Ruben,Miranda, Rene,Arroyo, Gabriel,Tamariz, Joaquin,Delgado, Francisco
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- Organic reactions in ionic liquids: Ionic liquid promoted Knoevenagel condensation of aromatic aldehydes with (2-thio)barbituric acid
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The Knoevenagel condensation of aromatic aldehydes with (2-thio)barbituric acid proceeded efficiently in reusable ionic liquids, EAN, BmimBF4, and BmimPF6 at room temperature in the absence of any catalyst with high yields.
- Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
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- Synthesis and Antimycobacterial Activity of 5-(Arylmethylene)Hexahydropyrimidine-2,4,6-Triones
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A series of 5-(arylmethylene)hexahydropyrimidine-2,4,6-triones were synthesized. Their antimycobacterial activity and acute daily toxicity with respect to M. lufu were investigated.
- Luzhnova,Tyrkov,Gabitova
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- The synthesis and evaluation of near-infrared probes with barbituric acid acceptors for in vivo detection of amyloid plaques
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A new array of near-infrared probes containing barbituric acid acceptors has been developed as Aβ imaging agents. These probes displayed long-emission wavelengths and large Stokes shifts, as well as high affinities for Aβ aggregates. In vivo and ex vivo studies demonstrated that BBTOM-3 could intensely label Aβ plaques in the brains of transgenic mice.
- Zhou, Kaixiang,Fu, Hualong,Feng, Liang,Cui, Mengchao,Dai, Jiapei,Liu, Boli
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- SiO2?12WO3?24H2O: A highly efficient catalyst for the synthesis of 5-arylidene barbituric acid in the presence of water
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The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO212WO324H2O in aqueous media at room temperature gave 5-arylidene barbituric acid in high yields with or without the use of ultrasound, providing a simple and efficient route to synthesis of these compounds.
- Li, Ji-Tai,Sun, Ming-Xuan
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- Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push–pull electronic systems: Experimental and quantum chemical study
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Electronic interactions in donor-π-linker-acceptor systems with barbituric acid as an electron acceptor and possible electron donor were investigated to screen promising candidates with a push–pull character based on experimental and quantum chemical studies. The tautomeric properties of 5-benzylidenebarbituric acid derivatives were studied with NMR spectra, spectrophotometric determination of the pKa values, and quantum chemical calculations. Linear solvation energy relationships (LSER) and linear free energy relationships (LFER) were applied to the spectral data - UV frequencies and 13C NMR chemical shifts. The experimental studies of the nature of the ground and excited state of investigated compounds were successfully interpreted using a computational chemistry approach including ab initio MP2 geometry optimization and time-dependent DFT calculations of excited states. Quantification of the push–pull character of barbituric acid derivatives was performed by the 13CNMR chemical shift differences, Mayer π bond order analysis, hole-electron distribution analysis, and calculations of intramolecular charge transfer (ICT) indices. The results obtained show, that when coupled with a strong electron-donor, barbituric acid can act as the electron-acceptor in push–pull systems, and when coupled with a strong electron-acceptor, barbituric acid can act as the weak electron-donor.
- Stojiljkovi?, Ivana N.,Ran?i?, Milica P.,Marinkovi?, Aleksandar D.,Cvijeti?, Ilija N.,Mil?i?, Milo? K.
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- Structurally simple D–A-type organic sensitizers for dye-sensitized solar cells: effect of anchoring moieties on the cell performance
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Abstract: In this work, we report synthesis and device fabrication studies of four metal-free D–A-type dyes (A1–A4) based on structurally simple N,N-dimethyl-4-vinyl aniline carrying four different acceptor/anchoring groups, as sensitizers for sensitizing photoanode (TiO2). In the sensitizers, N,N-dimethylaniline ring acts as an electron donor, while barbituric acid, N,N-dimethyl barbituric acid, thiobarbituric acid and N,N-diethyl thiobarbituric acid function as electron acceptor/anchoring units. They were synthesized in good yield via Knoevenagel protocol in neutral condition without any catalyst. Further, they were subjected to structural, electrochemical and optical characterization in order to evaluate their structure, band gap and absorption/emission behavior. The studies reveal that all the four dyes have thermodynamic feasibility of electron injection as well as electron recombination; their optical band gaps were found to be in the range of 2.35–2.56?eV. High-quality crystals of A2 and A4 were grown by slow evaporation technique using its solution with 1:1 pet ether (60–80?°C)/ethyl acetate solvent mixture at room temperature. Their SC-XRD studies disclose that the crystals are in the triclinic system with space group P-1. Further, DFT studies were performed using Turbomole V7.1 software package to evaluate their optimized geometry and HOMO and LUMO levels. Finally, DSSC device fabricated with the dye A1 showed relatively good efficiency when compared to other dyes mainly due to the effective binding of barbituric acid on the surface of TiO2 through NH or OH functional group. Graphical Abstract: [Figure not available: see fulltext.].
- Naik, Praveen,Su, Rui,Babu, Dickson D.,El-Shafei, Ahmed,Adhikari, Airody Vasudeva
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- Preparation of 5,5′-pyrilidene and 5,5′-quinolidene bis-barbituric acid derivatives
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NMR reaction following experiments were used to find optimal conditions for the barbituric acid double addition to aromatic and heteroaromatic carboxaldehydes. It was established that aromatic aldehydes with electron-donating substituents such as hydroxy, methoxy, and dimethylamino produce only the single addition barbituric acid adduct (barbituric acid benzylidenes). If these electron-donating substituents are transformed into electron-withdrawing substituents by virtue of protonation (NMe2 to NHMe2+) then the double barbituric acid adduct becomes the sole product of the reaction. This is also true regardless of the reaction media if strong electron-withdrawing substituents (such as a nitro group) are present. Considering that the reactive species for nitrogen containing aromatic heterocycles are actually the conjugated acids (electron deficient molecule) only the double barbituric acid adducts are isolated. All synthetic procedures presented are applicable to multi-gram scale preparations of double barbituric acid adducts.
- Jursic, Branko S.,Neumann, Donna M.
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- A study on the physical properties of low melting mixtures and their use as catalysts/solvent in the synthesis of barbiturates
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In recent years, deep eutectic solvents have become attractive due to their interesting characteristics such as, physicochemical properties, low cost of components, easiness to prepare, low toxicity, bio-renewability, and biodegradability. In order to make the deep eutectic mixture more cost-effective and renewable, carbohydrate derivatives were linked with deep eutectic mixtures, since, carbohydrates are the most important and widespread renewable compounds on the earth. In this work, we have used low melting mixtures comprised of carbohydrates to create the reaction media for organic transformations. The physical properties such as density, viscosity, acidity, refractive index, surface tension, solubility, glass transition temperature, thermal stability, solvent polarity, and toxicity of the mixture were studied. Low melting mixtures were used as reaction media and catalysts for the effective synthesis of Barbiturates. The reaction between aldehydes and barbituric acid/thiobarbituric acid, and the reaction between aldehydes, barbituric acid/thiobarbituric acid, and malononitrile/dimedone were performed effectively with good to excellent yields. The recyclability of the catalyst/solvent was also established.
- Theresa, Letcy Vincent,Avudaiappan, Govindan,Shaibuna, Machingal,Hiba, Kottayil,Sreekumar, Krishnapillai
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p. 1849 - 1860
(2021/06/17)
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- Barbituric acid based fluorogens: Synthesis, aggregation-induced emission, and protein fibril detection
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Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced emission, are systematically characterized. Afterward, the structure-property relationships of these barbituric acid based fluorogens are discussed. Finally, we demonstrate their potential applications for protein amyloid fibril detection.
- Ding, Siyang,Yao, Bicheng,Schobben, Louis,Hong, Yuning
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- Verjuice as a green and bio-degradable solvent/catalyst for facile and eco-friendly synthesis of 5-arylmethylenepyrimidine-2,4,6-trione, pyrano[2,3-d]pyrimidinone and pyrimido[4,5-d]pyrimidinone derivatives
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Verjuice (unripe grape juice), a natural mixture of organic acids, which is identified by pH-metric and TGA analysis, is efficiently used for the promotion of the synthesis of 5-arylmethylenepyrimidine-2,4,6-triones, via Knovenagel condensation reaction between barbituric or thiobarbituric acid and aldehydes. Verjuice is also employed for the effective synthesis of pyrano[2,3-d]pyrimidinone derivatives via a three-component reaction of barbituric acid or its thio analogue, aldehydes and malononitrile. In the same way, pyrimido[4,5-d]pyrimidinone derivatives are simply produced via the reaction of barbituric acid, aldehydes and urea or thiourea in the presence of verjuice. This green methodology rewards notable advantages including simple procedures, acceptable reaction times, easy work-up, high yields, circumventing the use of any expensive starting materials, volatile and hazardous organic solvents during the reaction and work-up process, and use of a natural, low-cost, reusable, and bio-degradable catalyst.
- Safari, Niloufar,Shirini, Farhad,Tajik, Hassan
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p. 887 - 897
(2019/03/27)
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- Microwave-associate synthesis of Co3O4 nanoparticles as an effcient nanocatalyst for the synthesis of arylidene barbituric and Meldrum's acid derivatives in green media
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In this study, Co3O4 nanocatalysts were constructed in environmentally appropriate conditions using controlled, effective, and facile microwave method. The final nanostructures were characterized by SEM, XRD, and TEM analyses. The products had a small size distribution, homogeneous morphology, and crystallographic structures associated with the formation of Co3O4 nanostructures. Moreover, EDS mapping analysis confirmed the existence of Co and O elements in the final structure, and the magnetic properties of the samples were investigated by VSM. The application of this nanostructure in a catalytic process was further examined, and the results suggested that it could be used as a novel candidate for the synthesis of arylidene barbituric and Meldrum,s acid through Knoevenagel condensation of aldehydes by barbituric and Meldrum,s acid in aqueous media. The high yield of these nanocatalysts would be justified by the nature of the nanostructure as well as the experimental procedure developed in this study, which affected the physicochemical features of the products.
- Yahyazadehfar, Mahdieh,Sheikhhosseini, Enayatollah,Ahmadi, Sayed Ali,Ghazanfari, Dadkhoda
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- The introduction of two new imidazole-based bis-dicationic Br?nsted acidic ionic liquids and comparison of their catalytic activity in the synthesis of barbituric acid derivatives
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In this article, the preparation of bis-imidazolium hydrogen sulfate and bis-imidazolium perchlorate as two new bis-dicationic Br?nsted acidic ionic liquids based on imidazole is reported. After characterization by FT-IR, mass and NMR spectroscopy and pH titration, the applicability of these reagents is studied in the promotion of the synthesis of 5-arylidene barbituric acids and pyrano[2,3-d] pyrimidinone derivatives. These methods possess some advantages such as ease of preparation of the catalyst, simple work-up procedure, short reaction times, excellent yields, and use of nonorganic solvents during all steps of the reactions and good reusability of the catalysts.
- Daneshvar, Nader,Nasiri, Mitra,Shirzad, Maryam,Safarpoor Nikoo Langarudi, Mohaddeseh,Shirini, Farhad,Tajik, Hassan
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p. 9744 - 9756
(2018/06/18)
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- 4-(4-Propylpiperazine-1-yl)butane-1-sulfonic acid-modified silica-coated magnetic nanoparticles: A novel and recyclable catalyst for the synthesis of 5-arylidinebarbituric acids and pyrano[2,3-d]pyrimidinedione derivatives in aqueous media
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A mild, simple and efficient procedure for the preparation of barbituric acid and pyrano[2,3-d]pyrimidine derivatives in aqueous media is described using 4-(4-propylpiperazine-1-yl)butane-1-sulfonic acid-modified silica-coated magnetic nanoparticles as a novel and reusable catalyst. The catalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least eight times without significant degradation in activity.
- Pourghasemi-Lati,Shirini,Alinia-Asli,Rezvani
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- Catalyst-free synthesis of benzimidazole and benzothiazole derivatives by the cleavage of the C–C double bond of 5-arylidenepyrimidine-2,4,6-(1H,3H,5H)-triones
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Background: Benzimidazole and benzothiazole subunits exist in many biologically active molecules, natural products, and synthetic compounds. These compounds have recently gained widespread interest due to their key role in medically important compounds, such as those exhibiting anticancer activity, antimicrobial activity, inhibition of hepatitis C virus NS5B polymerase, p38 kinase inhibitory activity, and anti-inflammatory activity. Methods: 2-Substituted benzimidazole and benzothiazole derivatives have been synthesized by the condensation of 1,2-phenylenediamine or 2-aminobenzothiophenol with 5-arylidenepyrimidine-2,4,6-(1H,3H, 5H)-trione derivatives via cleavage of C-C double bond without using a catalyst in EtOH under reflux conditions. Results: We report here a very simple, novel, efficient, and catalyst-free method for the synthesis of benzimidazole and benzothiazole in good to excellent yields from the treatment of 1,2-phenylenediamine and 2-aminothiophenol with various 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione, respectively. This reaction proceeds via cleavage of a C=C double bond and elimination of barbituric acid. Conclusion: This method appears to be general for the synthesis of benzimidazoles and benzothiazoles using 5-arylidenepyrimidine-2,4,6-(1H,3H,5H)-trione derivatives containing various aromatic and heteroaromatic aldehydes such as furfural and thiophene-2-carbaldehyde with electron-withdrawing and electron-releasing groups.
- Darehkordi, Ali,Ramezani, Mahin,Rahmani, Fariba,Poor, Mahboobe Amirani
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p. 290 - 294
(2018/04/20)
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- Succinimidinium N-sulfonic acid hydrogen sulfate as an efficient ionic liquid catalyst for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione and pyrano[2,3-d]pyrimidinone derivatives
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Succinimidinium N-sulfonic acid hydrogen sulfate ([SuSA-H]HSO4) as a new ionic liquid is prepared and characterized using a variety of techniques, including infrared spectra (FT-IR), 1H and 13C NMR, scanning electron microscopy, a mass spectra method, as well as by Hammett acidity function. The prepared reagent is efficiently able to catalyze the preparation of 5-arylmethylene-pyrimidine-2,4,6-triones via the condensation of aldehydes and barbituric acid. Further studies showed that the condensation of aldehydes with barbituric acid and malononitrile leading to pyrano[2,3-d]pyrimidinone derivatives can also be efficiently promoted in the presence of this reagent. The present methodology offers several advantages, including ease of the preparation and handling of the catalyst, simple and easy work-up, short reaction times, high yields of the products and recyclability of the catalyst.
- Abedini, Masoumeh,Shirini, Farhad,Mohammad-Alinejad Omran, Javad,Seddighi, Mohadeseh,Goli-Jolodar, Omid
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p. 4443 - 4458
(2016/07/06)
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- DABCO-based ionic liquids: Green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media
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A new and straightforward method for the synthesis of 5-arylidine barbituric and thiobarbituric acids through a reaction between barbituric acid and its thio-analogue with aldehydes using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate ([DABCO](SO3H)2(HSO4)2) as an efficient catalyst has been reported. In this project, also the preparation of pyrano[2,3-d]-pyrimidinediones via the reaction of barbituric or thiobarbituric acid, malononitrile and aldehydes in the presence of this reagent and 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium chloride ([DABCO](SO3H)2(Cl)2) has been investigated. The structure of the products was characterized using IR, 1H NMR and 13C NMR spectroscopy. The present methodologies suggests several advantages such as ease of the preparation and handling of the catalysts, high yields, simple and green procedures, low cost, short reaction times, easy work-up and preformation of the reaction in water as a green solvent.
- Seyyedi, Narges,Shirini, Farhad,Nikoo Langarudi, Mohaddeseh Safarpoor
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p. 44630 - 44640
(2016/06/09)
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- Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives
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1,8-Dioxo-octahydro-xanthenes are easily prepared via the condensation of aldehydes with 1,3-cyclohexadione and/or dimedone using N-sulfonated DABCO as a new and efficient catalyst. This reagent is also efficiently able to catalyze the condensation of aldehydes with barbituric acid leading to 5-arylmethylene-pyrimidine-2,4,6-triones. The structure of the products was characterized by their IR, 1H NMR, and 13C NMR spectroscopy. The present methodology offers several advantages such as ease of preparation and handling of the catalyst, high yields, simple and green procedure, low cost, short reaction times, easy work-up, and preformation of the reaction in the absence of solvent or in water as a green solvent.
- Shirini, Farhad,Langarudi, Mohaddeseh Safarpoor Nikoo,Seddighi, Mohadeseh,Jolodar, Omid Goli
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p. 8483 - 8497
(2015/01/30)
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- Colorimetric detection of fluoride ion by 5-arylidenebarbituric acids: Dual interaction mode for fluoride ion with single receptor
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Two 5-arylidenebarbituric acid derivatives (IH and IM) have been synthesized by the Knoevenagel condensation of barbituric acid with 4-N,N-dimethylamino benzaldehyde and studied for anion sensing activities. Both receptors sense fluoride ion with high selectivity and sensitivity and the sensing action has been demonstrated by naked eye detection, UV-visible absorption, and fluorescence spectral changes in the presence of F-. Indeed, the F- sensing mechanism for receptor IH depends on F - ion concentration. While at higher concentrations F- forms strong hydrogen bonding interaction with the N-H proton of the receptor, at lower concentrations sensing is influenced by the deprotonation of the methylene proton, followed by the chemical reaction, which is also confirmed by the 1H-NMR technique. On the other hand, when replacing the N-H proton with a methyl group, IM does not show any concentration dependent behaviour with F-. The F- concentration dependent sensing is attributed to the changes in the receptor-anion interaction equilibrium, where at higher F- concentrations, F- interacts with the receptor through hydrogen bonding and at lower concentrations it induces a chemical reaction.
- Saravanan, Chinnusamy,Easwaramoorthi, Shanmugam,Wang, Leeyih
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p. 5151 - 5157
(2014/04/03)
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- Anomalous reaction of hydrazine hydrate with 5-arylidene barbiturates: Formation of benzalazines
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Reaction of 5-arylidene barbiturates (3a-i) with hydrazine hydrate resulted in the unusual formation of novel benzalazines (5a-i) in 70-90% yield rather than the expected pyrazole fused pyrimidines.
- Goudgaon,Upendar Reddy, Ch.,Patil, Sharanabasappa,Sheshikant
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p. 277 - 282
(2019/01/21)
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- Organocatalyzed and uncatalyzed C=C/C=C and C=C/C=N exchange processes between knoevenagel and imine compounds in dynamic covalent chemistry
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Molecular diversity generation through reversible component exchange has acquired great importance in the last decade with the development of dynamic covalent chemistry. We explore here the recombination of components linked by C=C and C=N bonds through reversible double-bond formation, and cleavage in C=C/C=C and C=C/C=N exchange processes. The reversibility of the Knoevenagel reaction has been explored, and C=C/C=C C/C exchanges have been achieved among different benzylidenes, under organocatalysis by secondary amines such as L-proline. The substituents of these benzylidenes were shown to play a very important role in the kinetics of the exchange reactions. L-Proline is also used to catalyze the reversible C=C/C=C exchange between Knoevenagel derivatives of barbituric acid and malononitrile. Finally, the interconversion between Knoevenagel derivatives of dimethylbarbituric acid and imines (C=C/C=N exchange) has been studied and was found to occur rapidly in the absence of catalyst. The results of this study pave the way for the extension of dynamic combinatorial chemistry based on C=C/C=C and C=C/C=N exchange systems.
- Kulchat, Sirinan,Meguellati, Kamel,Lehn, Jean-Marie
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p. 1219 - 1236
(2015/04/14)
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- Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
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Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.
- Neumann, Donna M.,Cammarata, Amy,Backes, Gregory,Palmer, Glen E.,Jursic, Branko S.
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p. 813 - 826
(2014/01/23)
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- Antibacterial activities of some arylidene barbiturate derivatives
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A series of arylidene barbiturates 1-18 has been synthesized and evaluated against a number of Gram-positive and Gram-negative bacterial strains. Chromenopyrimidinedione derivatives 16 and 18 were found to be the most active against a number of Gram-positive organisms while compound 13 also showed antimicrobial activity against four Gram-positive strains. No significant activity was observed against Gram-negative bacterial strains.
- Khan, Khalid Mohammed,Ali, Muhammad,Ahmad, Aqeel,Amyn, Afroze,Karim, Aneela,Khan, Momin,Parveen, Shahnaz
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p. 890 - 893
(2013/07/26)
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- Organocatalysis of c?£/c?£N and C?£C/ C?£N exchange in dynamic covalent chemistry
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The reversibly formed C?£N bond plays a very important role in dynamic covalent chemistry and the C?£N/C?£N exchange of components between different imine constituents to create dynamic covalent libraries has been extensively used. To facilitate diversity generation, we have investigated an organocatalyzed approach, using L-proline as catalyst, to accelerate the formation of dynamic libraries of [n×n] imine components. The organocatalysis methodology has also been extended, under somewhat modified conditions, to reversible C?£C/C?£N exchange processes between Knoevenagel derivatives of barbituric acid and imines, allowing for the generation of increased diversity. Copyright
- Wilhelms, Nadine,Kulchat, Sirinan,Lehn, Jean-Marie
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p. 2635 - 2651
(2013/03/13)
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- Facile Knoevenagel and domino Knoevenagel/Michael reactions using gel-entrapped base catalysts
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An efficient method for Knoevenagel condensation of arenecarbaldehydes with active methylene compounds such as barbituric acid and Meldrum's acid in the presence of gel-entrapped base catalysts is reported. The method has been extended to the one-pot synthesis of arylmethylene-bis[3-hydroxycyclohex-2-en-1- one] derivatives from dimedone (=5,5-dimethylcyclohexane-1,3-dione) and arenecarbaldehydes by using domino Knoevenagel/Michael reaction sequence. Copyright
- Shinde, Shital,Rashinkar, Gajanan,Kumbhar, Arjun,Kamble, Santosh,Salunkhe, Rajashri
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experimental part
p. 1943 - 1951
(2012/01/04)
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- Nickel nanoparticles catalyzed knoevenagel condensation of aromatic aldehydes with barbituric acids and 2-thiobarbituric acids
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An efficient route for the Knoevenagel condensation of aromatic aldehydes with barbituric acids and 2-thiobarbituric acids in the presence of polyvinyl pyrrolidone (PVP) stabilized Ni nanoparticles in ethylene glycol has been reported. A range of biologically important arylidene barbiturates were obtained in high yields (82-97%) in a very short reaction time. Graphical Abstract: A novel and highly efficient PVP-stabilized Ni nanoparticles catalyzed synthesis of arylidene barbiturates and arylidene 2-thiobarbiturates has been described.
- Khurana, Jitender M.,Vij, Kanika
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experimental part
p. 104 - 110
(2010/11/05)
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- Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice
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A large amount of evidence suggests that monocytes/macrophages infiltration is implicated in a variety of inflammatory diseases including acute liver injury. Monocyte chemoattractant protein 1 (MCP-1) plays a crucial role in the process of macrophages recruitment. We herein presented a small-molecule library and a feasible quick screening method of evaluating potency of inhibition of chemotaxis of RAW264.7 cells stimulated by MCP-1. Fifty-three small molecules were synthesized and screened, and four compounds (2g, 2h, 4f, and 6h) showed inhibitory effects with IC50 values range from 0.72 to 20.47 μM, with compound 4f being the most efficient. Further in vivo studies demonstrated that oral administration of 2g, 2h, 4f, or 6h decreases, most significantly for 4f, the serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) in ConA-induced acute livery injury BALB/c mice. Histopathological evaluation liver sections confirmed 4f as a potent, orally active compound for hepatoprotective effects against ConA-induced acute liver injury in BALB/c mice.
- Luo, Youfu,Ma, Liang,Zheng, Hao,Chen, Lijuan,Li, Rui,He, Chunmei,Yang, Shengyong,Ye, Xia,Chen, Zhizhi,Li, Zicheng,Gao, Yan,Han, Jing,He, Gu,Yang, Li,Wei, Yuquan
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experimental part
p. 273 - 281
(2010/05/02)
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- Synthesis, characterization and catalytic activity of Ce1Mg xZr1-xO2 (CMZO) solid heterogeneous catalyst for the synthesis of 5-arylidine barbituric acid derivatives
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A series of Ce1MgxZr1-xo2 (CMZO) mixed metal oxide with different molar ratio were prepared by simple co-precipitation method. The prepared materials were tested for their catalytic activity performance using Knoevenagel condensation of various aromatic aldehydes with barbituric acid under solvent-free condition in microwave. The best catalytic activity was obtained with CMZO (1:0.6:0.4). The synthesized materials were characterized by using XRD, FT-IR, SEM-EDS techniques.
- Rathod, Sandip B.,Gambhire, Anil B.,Arbad, Balasaheb R.,Lande, Machhindra K.
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experimental part
p. 339 - 343
(2010/08/19)
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- Synthesis of barbiturate-based methionine aminopeptidase-1 inhibitors
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The syntheses of a new class of barbiturate-based inhibitors for human and Escherichia Coli methionine aminopeptidase-1 (MetAP-1) are described. Some of the synthesized inhibitors show selective inhibition of the human enzyme with high potency.
- Haldar, Manas K.,Scott, Michael D.,Sule, Nitesh,Srivastava,Mallik, Sanku
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p. 2373 - 2376
(2008/09/20)
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- A new and efficient method for the synthesis of 5-arylmethylene- pyrimidine2,4,6-trione under solvent and catalyst free conditions
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A new and efficient method has been developed for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione without any catalyst and solvent under microwave irradiation. A number of condensation products are prepared in very short reaction time with high yields.
- Sanjeeva Reddy,Nagaraj,Jalapathi
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p. 660 - 663
(2008/09/18)
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- Reaction of hexahydropyirimidine-2,4,6-trione with naphthalen-2-amine and benzaldehydes
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Previously unknown 12-aryl-7,8,9,10,11,12-hexahydrobenzo[f]pyrimido[4,5-b] quinoline-9,11-diones were synthesized by three-component condensation of naphthalen-2-amine with substituted benzaldehydes and barbituric acid through intermediate 5-benzylidenebarbituric acids. Nauka/Interperiodica 2007.
- Kozlov,Basalaeva
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p. 432 - 438
(2007/10/03)
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- PHAMACEUTICAL PREPARATIONS COMPRISING INSULIN
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Novel preparations comprising ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer wherein the ligand is extended by protamine that are capable of prolonging the ac-tion of insulin preparations.
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Page/Page column 146
(2010/02/15)
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- Efficient method for synthesis of the derivatives of 5-arylidene barbituric acid catalyzed by aminosulfonic acid with grinding
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Aminosulfonic acid is an environmentally friendly catalyst. Grinding a mixture of aromatic aldehydes, barbituric acid, and H2NSO 3H at room temperature (without any solvent) gave 5-arylidene barbituric acid in high yields, providing a simple and efficient route to synthesis of these compounds. Copyright Taylor & Francis Group, LLC.
- Li, Ji-Tai,Dai, Hong-Guang,Liu, Da,Li, Tong-Shuang
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p. 789 - 794
(2007/10/03)
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- Stabilised insulin compositions
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The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.
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Page/Page column 66
(2008/06/13)
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- Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
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Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.
- Jursic, Branko S.,Stevens, Edwin D.
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p. 2203 - 2210
(2007/10/03)
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- Knoevenagel condensation of aldehydes with cyclic active methylene compounds in water
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A new route of Knoevenagel condensation of aromatic aldehydes with Meldrum's acid, barbituric acid and dimedone in the presence of cetyltrimethyl ammonium bromide at room temperature in water is described.
- Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi,Jing, Xiuping
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p. 1947 - 1952
(2007/10/03)
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- Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
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Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).
- Jursic, Branko S.,Neumann, Donna M.
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p. 4103 - 4107
(2007/10/03)
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- Molecular hyperpolarizabilities of barbituric acid and cyclobutene-1,2- dione derivatives. Electronic and steric effects
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A series of merocyanine dyes containing various donors and barbituric acid and cyclobutene-1,2-dione moieties as the acceptors have been synthesized and their first-order hyperpolarizabilities β were determined. The β values of barbituric acid derivatives increase as the strength of the donor is increased from 4-dimethylaminophenyl to trimethylindolinyl to benzothiazolinyl, apparently due to the gradual decrease in the bond length alternation (BLA) from a large positive value to an optimum one by a stronger donor. In contrast, the β values for the cyclobutene-1,2-dione derivatives decrease with the same variation of the donors even though the cyclobutene-1,2-dione is a poorer acceptor than the barbituric acid moiety. The results have been attributed to the electron-donating ability of the donors and the increased distortion of the chromophores from planarity.
- Cho, Bong Rae,Je, Jong Tae,Lee, Seung Jae,Lee, Sang Hae,Kim, Hyun Soo,Jeon, Seung Joon,Song, Ok-Keun,Wang
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p. 2141 - 2144
(2007/10/03)
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- New Aspects in the Reaction of Azomethines with Cyclic CH-Acidic Compounds
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Treatment of substituted benzylidene anilines 1a - f with cyclic CH-acidic compounds 2a - m in ethanol at room temperature yields in addition/elimination reactions the corresponding arylidene derivatives 4 and the 2:1 adducts 5.The addition products 3, which are formed as intermediates, could not be isolated in any case.The donor/acceptor effect of the substituents on the benzylidene moiety influences to a significant extent the reactivity towards the azomethine carbon. Keywords.Azomethine; CH-Acidic compound; Addition/elimination reaction.
- Hennig, Lothar,Alva-Astudillo, Mario,Mann, Gerhard,Kappe, Thomas
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p. 571 - 580
(2007/10/02)
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- Kinetics and mechanism of reaction of barbituric acids with p-dimethylaminobenzaldehyde and N,N-dimethyl-p-nitrosoaniline
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The condensation reactions of barbituric acid (I) and thiobarbituric acid (II) with p-dimethylaminobenzaldehyde (III) and N,N-dimethyl-p-nitrosoaniline (IV) in methanolic medium have been investigated spectrophotometrically at 10-55 deg C.These reactions follow overall second order kinetics, first order each in reactants.The rate-determining step involves dehydration of the aldol intermediate (XI).From the dependence of the rate constants on temperature activation parameters have been calculated.The solvent effect on the reaction rate has been investigated and therate decreases with decrease in dielectric constant.
- Girgis, Maher M,El-Shahawy, A S
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- Clay Catalysis: Dry Condensation of Barbituric Acid with Aldehydes under Microwave Irradiation
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Barbituric acid (1) and arylcarboxyaldehydes (2) were condensated to 5-(arylmethylene)-2,4,6 (1H,3H,5H) pyrimidinetrione (3) in presence of acidic clay KSF without solvent under microwave irradiation.
- Villemin, Didier,Labiad, Bouchta
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p. 3333 - 3337
(2007/10/02)
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