- Knoevenagel condensation in aqueous media promoted by 2,2′-bipyridinium dihydrogen phosphate as a green efficient catalyst
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A 2,2′-Bipyridine-based ionic compound named 2,2′-bipyridinium dihydrogen phosphate was synthesized by addition of phosphoric acid to a solution of 2,2′-Bipyridine in dichloromethane. After the characterization using FT-IR, mass, 1H, 13C and 31P NMR techniques, it was used as a Bronsted dicationic acidic catalyst for the promotion of the synthesis of 2-arylidene malononitrile and 5-arylidene barbituric acid derivatives via Knoevenagel condensation reaction in water. Some of the advantages of this method are the utilization of an easy preparable, cost-effective and eco-friendly organic salt as a catalyst within high rates and yields of the reactions, simple and quick work-up and acceptable reusability of the catalyst.
- Darvishzad, Shila,Daneshvar, Nader,Shirini, Farhad,Tajik, Hassan
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p. 2973 - 2984
(2021/04/19)
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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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- 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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- Sulfamic Acid Catalyzed Atom Economic, Eco-friendly Synthesis of Novel 7-(Aryl)-10-thioxo-7,9,10,11-tetrahedro-6H-pyrimido-[5′4′:5,6]pyrano[3,2-c]quinoline-6,8(5H)-dione and its Derivatives
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A series of novel 7-(3-chloro-phenyl)-10-thioxo-7,9,10,11-tetrahedro-6H-pyrimido-[5′4′:5,6] pyrano[3,2-c]quinoline-6,8(5H)-dione derivatives have been synthesized through the multi-component condensation of aromatic aldehydes, barbituric acid, and 2,4-dih
- Jadhav, Sunetra J.,Patil, Reshma B.,Kumbhar, Digambar R.,Patravale, Ajinkya A.,Chandam, Dattatraya R.,Deshmukh, Madhukar B.
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p. 2206 - 2215
(2017/07/25)
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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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- 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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p. 457 - 463
(2016/01/30)
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- NH4Cl mediated new protocol for the synthesis of 5-arylidene barbiturates
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Eco-benign method for synthesizing arylidene barbiturates has been developed by using ammonium chloride (NH4Cl) in stoichiometric amount, as an enolization activator, in water. Execution of methodology is simple, products obtained in high yield
- Mohammed Khan, Khalid,Alia, Muhammad,Khana, Momin,Taha, Muhammad,Perveen, Shahnaz
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experimental part
p. 28 - 32
(2012/04/10)
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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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- 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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experimental part
p. 353 - 355
(2009/09/06)
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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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- 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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- Synthesis and antibacterial activity of 2-substituted 5-(1,2-diarylethyl)-4,6-dichloropyrimidine derivatives
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A series of 5-(1,2-diarylethyl)-2,4,6-trichlorapyrimidines and 2-amino- and 2-(1-piperazinyl)-5-(1,2-diarylethyl)-4,6- dichloropyrimidines were synthesized via organozinc reagents. These new pyrimidine derivatives were tested against human bacterial flora
- Fellahi,Dubois,Mandin,Ombetta-Goka,Guenzet,Chaumont,Frangin
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p. 633 - 639
(2007/10/02)
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- Synthesis of a New Class of Uridine Phoshorylase Inhibitors
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A new series of potent uridine phosphorylase inhibitors have been prepared from barbituric acid.Among them 1--5-(m-benzyloxy)benzylbarbituric acid (37, BBBA) is the most promising having a Ki value of 1.1 +/- 0.2 nM wit
- Tzeng, Cherng-Chyi,Panzica, Raymond P.,Naguib, Fardos N.M.,Kouni, Mahmoud H. el
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p. 1399 - 1404
(2007/10/02)
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