- Synthesis and catalytic activity of a novel ionic liquid-functionalized metal–organic framework
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In this research, a new heterogeneous catalyst is fabricated through covalent modification of iron-based metal–organic framework with ionic liquid. In more detail, using 2-aminoterephthalic acid and iron (III) chloride hexahydrate, amino-functionalized me
- Sadjadi, Samahe,Koohestani, Fatemeh
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p. 291 - 306
(2021/09/07)
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- Polyionic liquid decorated chitosan beads as versatile metal-free catalysts for catalyzing chemical reactions in aqueous media
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A new strategy is presented for enhancing the catalytic activity of cross-linked chitosan beads. More precisely, chitosan beads were cross linked with glutaraldehyde and then, vinyl functionalized. In the next step, the vinyl-functionalized beads were pol
- Koohestani, Fatemeh,Sadjadi, Samahe
-
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- New advances in catalytic performance of erbium-folic acid-coated CoFe2O4 complexes for green one-pot three-component synthesis of pyrano[2,3-d]pyrimidinone and dihydropyrano[3,2-c]chromenes compounds in water
-
In the current research, much attention is paid to heterogenized nanostructure. Herein, we report the green synthesis magnetic nanoparticles (MNPs) of cobalt ferrite by the immobilization of erbium (Er) coated with folic acid (FA) which show effective cat
- Sorkhabi, Serve,Mozafari, Roya,Ghadermazi, Mohammad
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- Efficient biogenesis of Cu2O nanoparticles using extract of Camellia sinensis leaf: Evaluation of catalytic, cytotoxicity, antioxidant, and anti-human ovarian cancer properties
-
At the moment, metallic nanoparticles especially copper nanoparticles are administrated for the cure of different disorders, such as tumor and cancer. In recent years, many chemotherapeutic supplements have been formulated by copper nanoparticles. In the
- Dou, Lei,Zhang, Xinxin,Zangeneh, Mohammad Mahdi,Zhang, Yi
-
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- 4,4'-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel-Michael condensation
-
Liquid phase tandem Knoevenagel-Michael condensation of various aromatic and heteroaromatic aldehydes with barbituric acid or 2-thiobarbituric acid and malononitrile was studied in a one-pot three-component reaction. For the first time, TMDP was employed as a safe and efficient solvent and/or catalyst in the liquid and aqueous ethanol medium, respectively, for the practical and eco-friendly Knoevenagel-Michael condensation. The reactions were carried out by using greener procedures, including a) the use of TMDP as an N-heterocycle organocatalyst in a green medium including water and ethanol (1:1 v/v) at reflux temperature, and b) the use of TMDP as a dual solvent-catalyst at 65 °C in the absence of any solvent. High to excellent yields of the desired pyrano[2,3-d] pyrimidinones were obtained under the two earlier mentioned conditions. The current methodologies have advantages, including (a) avoiding hazardous, toxic, volatile, and flammable materials and solvents, (b) avoiding tedious processes, harsh conditions, and multiple steps for the preparation of catalysts, (c) using a less toxic and noncorrosive catalyst, (d) minimizing hazardous waste generation and simple workup process, and (e) high recyclability of TMDP. Another important result of this work is that the TMDP can be a promising alternative for toxic, volatile, and flammable base reagents such as piperidine and triethylamine in liquid phase organic syntheses owing to its unique properties such as being less toxic, nonflammable, and nonvolatile, and having a low melting point, broad liquid range temperature, high thermal stability, and safe handling and storage.
- Zaharani, Lia,Ghaffari Khaligh, Nader,Gorjian, Hayede,Rafie Johan, Mohd
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p. 261 - 268
(2021/03/16)
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- Synthesis of Pyrano[2,3-d]pyrimidine-2,4-diones and Pyridino[2,3-d]pyrimidine-2,4,6,8-tetraones: Evaluation Antitumor Activity
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A series of some novel pyrano[2,3-d]pyrimidine 4–10 with 75–95% yields and pyridino[2,3-d]pyrimidine derivatives 11–16 with 75–92% yields is reported. The building structures have been achieved by reaction of 5-arylidene barbituric acid 2 and active nucle
- Haggam, Reda A.,Assy, Mohamed G.,Mohamed, Enaiat K.,Mohamed, Abdussattar S.
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p. 842 - 850
(2019/12/24)
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- Convenient and fast synthesis of various chromene pharmaceuticals assisted by highly porous volcanic micro-powder with nanoscale diameter porosity
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Herein, a volcanic-based mesoporous catalytic system is precisely characterized by various analytical methods and suitably used for facilitating the organic synthesis reactions. Briefly, high reaction yield (99percent) has been obtained in short reaction
- Maleki, Ali,Valadi, Kobra,Gharibi, Saideh,Taheri-Ledari, Reza
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p. 4113 - 4128
(2020/07/06)
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- An efficient one-pot three-component synthesis of 7-amino-2, 4-dioxo-5-aryl-1,3,4,5-tetrahydro-2 H-pyrano[2,3-d]pyrimidine-6-carbonitriles catalyzed by SnO2/SiO2 nanocomposite
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Abstract: We have developed a SnO2/SiO2 catalyzed efficient and rapid protocol for the synthesis of pyrano[2,3-d]pyrimidinone derivatives by the three-component cyclocondensation of aromatic benzaldehydes, malononitrile, and barbitur
- Yelwande, Ajeet A.,Lande, Machhindra K.
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p. 5479 - 5498
(2020/10/02)
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- Fabrication and characterization of adenine-grafted carbon-modified amorphous ZnO with enhanced catalytic activity
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Sustainability has become a countersign and guiding rule for current field of nanocatalysis. Herein, we report a cost-effective, greener, clean, and proficient process for the formation of adenine-grafted carbon-modified amorphous ZnO nanocatalyst (ZnO@AC
- Chowhan, Bushra,Gupta, Monika,Sharma, Neha
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- Efficient one-pot synthesis of pyrano[2,3-d]pyrimidinone and pyrido [2,3-d] pyrimidine derivatives by using of Mn-ZIF-8?ZnTiO3 nanocatalyst
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Mn-ZIF-8?ZnTiO3 nanocomposite was synthesized by sol-gel method. The morphology and structure of the nanocrystalline Mn-ZIF-8?ZnTiO3 was characterized by SEM, TEM, BET, XRD. The results confirmed the formation of Mn-ZIF-8?ZnTiO3 nanocomposite with particl
- Farahmand, Tayebeh,Hashemian, Saeedeh,Sheibani, Ali
-
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- SCMNPs@Urea/Py-CuCl2: a recyclable catalyst for the synthesis of pyrano[2,3-d]pyrimidinone and pyrano[2,3-d] pyrimidine-2,4,7-trione derivatives
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An efficient, simple, and mild strategy for the one-pot multicomponent synthesis of pyrano[2,3-d]pyrimidinone and pyrano[2,3-d]pyrimidine-2,4,7-trione derivatives is described using SCMNPs@Urea/Py-CuCl2 nanoparticles as a reusable heterogeneous magnetic nanocatalyst. The catalyst was characterized using Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), and scanning electron microscopy (SEM). The SCMNPs@Urea/Py-CuCl2 can be easily collected from the reaction solution by magnetic decantation using a permanent magnetic field and reused in six runs without significant decrease in catalytic activity.
- Zhang, Jun,Song, Hongqing,Cui, Ruirui,Deng, Chaoyong,Yousif, Qahtan A.
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p. 558 - 578
(2020/03/31)
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- A choline chloride-based deep eutectic solvent promoted three-component synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d] pyrimidinone (thione) derivatives
-
An efficient one-pot method for the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone (thione) derivatives through a three-component reaction between aldehydes, malononitrile and enolizable C–H activated acidic compounds using a new deep eutectic solvent made of choline chloride, urea and thiourea as an environmentally benign catalyst has been reported. The structure of the catalyst was characterized using FT-IR, 1H NMR, and 13C NMR. The present method exhibits some notable advantages such as ease of the preparation and handling of the catalyst, low cost, green reaction conditions, short reaction times, high yields, and simple work-up. Also, the catalyst could be recovered easily and recycled up to four times without significant loss of catalytic activity.
- Biglari, Mohammad,Shirini, Farhad,Mahmoodi, Nosrat O.,Zabihzadeh, Mehdi,Mashhadinezhad, Maryam
-
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- Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives
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—An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chrome
- Zabihzadeh, Mehdi,Omidi, Atefeh,Shirini, Farhad,Tajik, Hassan,Langarudi, Mohaddeseh Safarpoor Nikoo
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- Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2: a novel and efficient nano-catalyst for the one-pot three-component synthesis of pyran annulated bis-heterocyclic scaffolds under ultrasound irradiation
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In this study, a novel magnetically recoverable Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2 nano-particle was synthesized using a simple chemical coprecipitation approach. In the FT-IR spectroscopy of nano-particles, related
- Gholamhosseini-Nazari, Mahdi,Esmati, Somayeh,Safa, Kazem D.,Khataee, Alireza,Teimuri-Mofrad, Reza
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p. 1841 - 1862
(2019/01/04)
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- Isatin-SO3H coated on amino propyl modified magnetic nanoparticles (Fe3O4@APTES@isatin-SO3H) as a recyclable magnetic nanoparticle for the simple and rapid synthesis of pyrano[2,3-d] pyrimidines derivatives
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Isatin-SO3H coated on amino propyl modified magnetic nanoparticles (Fe3O4@APTES@isatin-SO3H) is found to be a novel, efficient, and reusable magnetic nanocatalyst, and characterized by FT-IR, SEM, TEM, XRD, EDX,
- Sajjadifar, Sami,Gheisarzadeh, Zohreh
-
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- Preparation and application of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide as new efficient ionic liquid catalyst for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives
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We report synthesis of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide ([TPPHSP]Br) as a reusable green Br?nsted-acidic ionic liquid catalyst and its application for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives by condensation reaction between aromatic aldehydes and barbituric acid or aromatic aldehydes, malononitrile, and barbituric acid in EtOH–H2O in reflux condition with good to excellent yield. The [TPPHSP]Br IL catalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), and thermogravimetric (TG) analysis and showed good catalytic activity and reusability.
- Karami, Samira,Momeni, Ahmad Reza,Albadi, Jalal
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p. 3395 - 3408
(2019/04/25)
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- Magnetic nanoporous MCM-41 supported ionic liquid/palladium complex: An efficient nanocatalyst with high recoverability
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In this study, a novel magnetic mesoporous MCM-41 silica supported ionic liquid/palladium complex (Fe3O4@MCM@IL/Pd) with core-structure was prepared and characterized and its catalytic performance was developed under green conditions
- Abaeezadeh, Somayeh,Elhamifar, Dawood,Norouzi, Meysam,Shaker, Masoumeh
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- Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations
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In the present work, 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) dichloride ([C4(MIm)2]·2Cl) and 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate ([C4(MIm)2]·2HSO4) were prepared via adequate, solvent-free methods and characterized using FT-IR, 1H NMR, 13C NMR, and potentiometric titration techniques. These reagents were investigated in the synthesis of 5-arylidene (thio)barbituric acids, 2-arylidene malononitriles, 4H-pyrans, and pyrano[2,3-d] pyrimidineones, and their catalytic activities were compared in the promotion of these reactions. Based on the obtained results, we found that [C4(MIm)2]·2Cl showed more catalytic efficiency where a basic or weak acidic media is needed. In contrast, [C4(MIm)2]·2HSO4 is a powerful catalyst in reactions needing acidic catalysts to enhance the reaction rate. Using these reagents, the products were formed under mild and eco-friendly conditions in excellent yields during short reaction times without needing column chromatography for work-up.
- Sharifi, Zahra,Daneshvar, Nader,Langarudi, Mohaddeseh Safarpoor Nikoo,Shirini, Farhad
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p. 4941 - 4958
(2019/07/03)
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- Synthesis of chloro, fluoro, and nitro derivatives of 7-amino-5-aryl-6-cyano-5H-pyrano pyrimidin-2,4-diones using organic catalysts and their antimicrobial and anticancer activities
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Chloro, fluoro, and nitro derivatives of 7-amino-5-aryl-6-cyano-5H-pyrano pyrimidin-2,4-diones were produced by reacting malononitrile, barbituric acid, and aromatic aldehydes together with a DABCO catalyst in an aqueous one-pot reaction. This is the firs
- Aremu, Oluwole S.,Singh, Parvesh,Singh, Moganavelli,Mocktar, Chunderika,Koorbanally, Neil A.
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p. 3008 - 3016
(2019/09/16)
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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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- Synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives using Fe3O4@Ph-PMO-NaHSO4 as a new magnetically separable nanocatalyst
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Immobilized NaHSO4 on core/shell phenylene bridged periodic mesoporous organosilica magnetic nanoparticles (Fe3O4@Ph-PMO-NaHSO4) as a new acidic magnetically separable nanocatalyst was successfully prepared in three steps: (i) preparation of Fe3O4 nanoparticles by a precipitation method, (ii) synthesis of an organic-inorganic periodic mesoporous organosilica structure with phenyl groups on the surface of Fe3O4 magnetic nanoparticles (MNPs) and (iii) finally adsorption of NaHSO4 on periodic mesoporous organosilica (PMO) network. The prepared organic-inorganic magnetic reagent was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), transmission electron microscopy (TEM), N2 adsorption-desorption and energy-dispersive X-ray (EDX) techniques. Finally, it was used as a reusable and new catalyst to promote the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives as important biologically active compounds. Eco-friendly protocol, high yields, short reaction times and easy and quick isolation of the products are the main advantages of this procedure.
- Haghighat, Mahdieh,Shirini, Farhad,Golshekan, Mostafa
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p. 3447 - 3458
(2019/05/10)
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- Butane-1-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles: A novel and heterogeneous catalyst for the one-pot synthesis of barbituric acid and pyrano[2,3-d] pyrimidine derivatives in aqueous media
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Butane-1-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-Sultone) was easily prepared via direct ring opening of 1,4-butanesultone with nanomagnetic Fe3O4@SiO2. The prepared reagent was characterized and used for the efficient promotion of the synthesis of barbituric acid and pyrano[2,3-d] pyrimidine derivatives. All reactions were performed under mild and completely heterogeneous reaction conditions affording products in good to high yields. The catalyst is easily isolated from the reaction mixture by magnetic decantation and can be reused at least eight times without significant loss in activity.
- Pourghasemi-Lati,Shirini,Alinia-Asli,Rezvani
-
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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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- Introduction of organic/inorganic Fe3O4@MCM-41@Zr-piperazine magnetite nanocatalyst for the promotion of the synthesis of tetrahydro-4H-chromene and pyrano[2,3-d]pyrimidinone derivatives
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Fe3O4@MCM-41@Zr-MNPs modified with piperazine is easily prepared and characterized using Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), N2 adsorption–desorption, Transmission electron micr
- Pourhasan-Kisomi, Reyhaneh,Shirini, Farhad,Golshekan, Mostafa
-
-
- Organocatalyzed domino reactions: diversity oriented synthesis of pyran-annulated scaffolds using in situ-developed benzylidenemalononitriles
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Molecular diversity for the synthesis of pyran annulated heterocyclic scaffolds has been achieved from the multicomponent reaction of aldehyde, malonitrile and a third participant such as dimedone, barbituric acid and 3-methyl-1H-pyrazol-5(4H)-one. The re
- Ahad, Abdul,Farooqui, Maqdoom
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p. 2445 - 2455
(2017/03/22)
-
- Green cellulose-based nanocomposite catalyst: Design and facile performance in aqueous synthesis of pyranopyrimidines and pyrazolopyranopyrimidines
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A cellulose-based nanobiocomposite decorated with Fe3O4 nanoparticles was prepared, characterized and applied as an easily recoverable and reusable green nanocatalyst in the synthesis of pyrano[2,3-d]pyrimidine derivatives in water a
- Maleki, Ali,Jafari, Abbas Ali,Yousefi, Somayeh
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p. 409 - 416
(2017/08/21)
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- Efficient synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives in presence of novel basic ionic liquid catalyst
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A basic ionic liquid, namely 1,1′-(butane-1,4-diyl)bis(1,4-diazabicyclo [2.2.2]octan-1-ium) hydroxide, was prepared and characterized using Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, and pH measurements. The ionic liquid was used for efficient promotion of the synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives at room temperature under grinding conditions. A simple procedure, short reaction time, high yields, non-column chromatographic separation, commercial availability of the starting materials, and recyclability of the catalyst are attractive features of this process.
- Jolodar, Omid Goli,Shirini, Farhad,Seddighi, Mohadeseh
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p. 1245 - 1251
(2017/07/10)
-
- Facile and simple synthesis of pyrimido[4,5-d]pyrimidinones and pyrano[2,3-d]pyrimidinones catalyzed by nano-sized NS-C4(DABCO-SO3H)2·4Cl
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In this work, 4,4′-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium)tetrachloride (NS-C4(DABCO-SO3H)2·4Cl), a newly reported nano-sized Br?nsted acid catalyst is used for the effective synthesis of pyrimido[4,5-d]pyrimidinones and pyrano[2,3-d]pyrimidinones derivatives. The products were formed under mild and environmentally friendly conditions in excellent yields over very short reaction times. Using green solvent and simple methodologies, no side reactions and use of inexpensive catalyst with lower loading are other advantages of this work.
- Goli-Jolodar, Omid,Shirini, Farhad
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p. 1235 - 1241
(2017/05/15)
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- Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol
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Preparation of pharmaceutically active 2-amino-4H-pyran derivatives has been achieved using cheap thiamine hydrochloride as catalyst. A wide range of aromatic aldehydes easily undergo condensation with malononitrile and several kinds of 1,3-cyclohexanedio
- Chen, Lu,Bao, Sunan,Yang, Lixiang,Zhang, Xian,Li, Bin,Li, Yibiao
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p. 3883 - 3891
(2017/06/20)
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- Preparation of a new DABCO-based ionic liquid [H2-DABCO][H2PO4]2} and its application in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives
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A new acidic ionic liquid, 1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen phosphate {[H2-DABCO][H2PO4]2}, was prepared in a quick and straightforward process and characterized by using different methods such as FT-IR, NMR and Mass analysis. Then it was used as a reusable and new catalyst to promote the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives as important biologically active compounds that they are used in pharmaceutical industry. This adequate procedure possess some advantages like producing target compounds in high yields, short reaction times, simple work-up procedure and use of chief and easily preparable catalyst.
- Shirini, Farhad,Langarudi, Mohaddeseh Safarpoor Nikoo,Daneshvar, Nader
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p. 268 - 278
(2017/04/06)
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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
-
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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- Three-component synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles in aqueous medium
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Pyrano[2,3-d]pyrimidine derivatives were synthesized via one-pot, three-component condensation reaction of aromatic aldehydes, malononitrile, and barbituric acid in aqueous ethanol catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fes
- Rezayati, Sobhan,Abbasi, Zahra,Nezhad, Eshagh Rezaee,Hajinasiri, Rahimeh,Farrokhnia, Abdolhadi
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p. 7597 - 7609
(2016/09/20)
-
- 4-Dialkylaminopyridine modified magnetic nanoparticles: As an efficient nano-organocatalyst for one-pot synthesis of 2-amino-4: H -chromene-3-carbonitrile derivatives in water
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A novel heterogeneous magnetic nano-organocatalyst was developed using immobilization of 4-dialkylaminopyridine moieties on Fe3O4 magnetic nanoparticles (MNP-DMAP). It was synthesized using the reaction of MNP-oxiran (MNPO) with N-methylpyridin-4-amine. The MNPO substrate was produced via oxidation of vinyl groups on the surface of vinyl-functionalized MNP (VMNP) using H2O2. To synthesis VMNP, silica-coated magnetic nanoparticles (Fe3O4@SiO2) were reacted with trimethoxy(vinyl)silane. The MNP-DMAP catalyst shows remarkable activity in the synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives using a multicomponent reaction under mild conditions in water as a green solvent. The MNP-DMAP was reusable in this process for at least 10 times without any treatment in its catalytic activity.
- Dangolani, Soheila Khajeh,Panahi, Farhad,Nourisefat, Maryam,Khalafi-Nezhad, Ali
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p. 92316 - 92324
(2016/10/09)
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- Mild and green synthesis of tetrahydrobenzopyran, pyranopyrimidinone and polyhydroquinoline derivatives and DFT study on product structures
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The multicomponent synthesis of 4H-benzo[b]pyran, pyranopyrimidinone and polyhydroquinoline derivatives has been achieved using catalytic amounts of calcium hydrogen phosphate in aqueous medium as a green, inexpensive and environmentally benign media. The
- Bodaghifard, Mohammad Ali,Solimannejad, Mohammad,Asadbegi, Sajad,Dolatabadifarahani, Samira
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p. 1165 - 1179
(2016/04/26)
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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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- Synthesis of pyran annulated heterocyclic scaffolds: A highly convenient protocol using dimethylamine
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A facile and rapid three-component synthesis of pharmaceutically diverse pyran annulated heterocycles has been developed via a one-pot condensation of aromatic aldehydes, malononitrile, and different enolizable C-H-activated acidic compounds in the presen
- Ramesh, Rathinam,Lalitha, Appaswami
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p. 8009 - 8017
(2015/02/19)
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- Nano-sawdust-OSO3H as a new, cheap and effective nanocatalyst for one-pot synthesis of pyrano[2,3-d]pyrimidines
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An atom-efficient, three-component synthetic methodology has been developed for the preparation of biologically important pyrano[2,3-d]pyrimidines using nano-sawdust-OSO3H as a new catalyst. The reaction involves the use of barbituric acid or t
- Sadeghi,Bouslik,Shishehbore
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p. 1801 - 1808
(2015/08/06)
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- Water Mediated Domino Knoevenagel-Michael-cyclocondensation Reaction of Malononitrile, Various Aldehydes and Barbituric Acid Derivatives Using Boric Acid Aqueous Solution System Compared with Nano-titania Sulfuric Acid
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Nano-titania sulfuric acid (TSA) and boric acid [B(OH)3] were efficiently utilized for domino Knoevenagel-Michael-cyclocondensation reaction of malononitrile, various aldehydes and barbituric acid derivatives to synthesis of pyrano[2,3-d]pyrimi
- Khazaei, Ardeshir,Nik, Heidar Ali Alavi,Moosavi-Zare, Ahmad Reza
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p. 675 - 679
(2015/09/02)
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- Bentonite-titana composite as an efficient, eco-friendly and non-toxic catalyst for synthesis of benzopyran derivatives under heating and solvent-free conditions
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Bentonite-titana composite was prepared and characterized by XRD, FT-IR and SEM. Results indicate that TiO2 particles have been supported on the bentonite layers and a delaminated structure is formed. Then the bentonitetitana composite as a mil
- Darehkordi, Ali,Hosseini, Mohammad Sadegh,Mosavi, Mirrasol,Poorfreidoni, Alireza
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p. 159 - 167
(2015/06/23)
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- Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: Synthesis, biological evaluation and docking studies
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A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the s
- Kaur, Ramandeep,Naaz, Fatima,Sharma, Sahil,Mehndiratta, Samir,Gupta, Manish Kumar,Bedi, Preet Mohinder Singh,Nepali, Kunal
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p. 3334 - 3349
(2015/08/03)
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- Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans
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Glycerol is applied as a green, biodegradable and reusable promoting medium for one-pot three component synthesis of 4H-pyrans under catalyst-free conditions. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatine derivatives
- Safaei, Hamid Reza,Shekouhy, Mohsen,Rahmanpur, Sudabeh,Shirinfeshan, Athar
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p. 1696 - 1704
(2013/02/22)
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- Zn[(L)proline]2: An efficient catalyst for the synthesis of biologically active pyrano[2,3-d]pyrimidine derivatives
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Biologically active pyrano[2,3-d]pyrimidine derivatives were efficiently synthesized in excellent yields by a three-component, one-pot condensation reaction of malononitrile, benzaldehydes, and barbituric acid using a catalytic amount of Zn[(L)proline]. C
- Heravi, Majid M.,Ghods, Azadeh,Bakhtiari, Khadijeh,Derikvand, Fatemeh
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experimental part
p. 1927 - 1931
(2010/09/05)
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- H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives
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This is a report of an efficient, clean and facile method for the synthesis of 1,4-dihydropyrano[2,3-c] pyrazole and pyrano[2,3d]pyrimidine derivatives via three-component one-pot condensation of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one or barbituric acid,
- Heravi,Ghods,Derikvand,Bakhtiari,Bamoharram
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experimental part
p. 615 - 620
(2010/11/05)
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- Eco-friendly and efficient synthesis of pyrano[2,3-d] pyrimidinone and tetrahydrobenzo[b]pyran derivatives in water
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Tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives were synthesized efficiently in the presence of KAl(SO4)2.12H2O (alum) in water. Green media, lack of toxicity, short reaction times, easy work-up and high yields are some advant
- Mobinikhaledi, Akbar,Foroughifar, Naser,Bodaghi Fard, Mohammad Ali
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experimental part
p. 179 - 185
(2010/10/19)
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- Tetrabutylammonium bromide in water as a green media for the synthesis of pyrano[2,3-d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives
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Tetrabutylammonium bromide (TBAB) was used as a green catalyst for the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives in water as a solvent. Use of nontoxic reaction components, short reaction times, easy work-up and high y
- Mobinikhaledi, Akbar,Fard, Mohammad Ali Bodaghi
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experimental part
p. 931 - 935
(2011/09/15)
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- Mechanochemical solvent-free and catalyst-free one-pot synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones with quantitative yields
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Solvent-free synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones by ball-milling and without any catalyst is described. This method provides several advantages such as being environmentally friendly, using a simple workup procedure, and affording high
- Mashkouri, Sara,Naimi-Jamal, M. Reza
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experimental part
p. 474 - 479
(2009/09/05)
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- A clean one-pot synthesis of 7-amino-5-aryl-6-cyano-1,5-dihydro-2H- pyrano[2,3-d] pyrimidine-2,4(3H)-diones in aqueous media under ultrasonic irradiation
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A novel approach to the synthesis of 7-amino-5-aryl-6-cyano-1,5-dihydro-2H- pyrano[2,3-d]pyrimidine-2,4(3H)-diones in aqueous media under ultrasonic irradiation without catalyst is described. This method provides several advantages such as being environmentally friendly, simple work-up procedure and milder condition. In addition, water was chosen as a green solvent.
- Jin, Tong-Shou,Liu, Li-Bin,Zhao, Ying,Li, Tong-Shuang
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p. 162 - 163
(2007/10/03)
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