Pyrimidinone Derivatives Research Articles

Efficient procedure with new fused pyrimidinone derivatives, Schiff base ligand and its La and Gd complexes by green chemistry

Synthetic strategies were developed for the construction of some newer more potent derivatives of thiobarbituric acid and its Schiff base metal complexes in both bulk and at the nanoscale.

Taurine as a green bio-organic catalyst for the preparation of bio-active barbituric and thiobarbituric acid derivatives in water media

Taurine, a β-amino acid that is abundantly available in the tissues of human and animals, is efficiently used as a green bio-organic catalyst in the preparation of some of the biologically active barbituric and thiobarbituric acid derivatives. In the presence of taurine, 5-Arylidene (thio) barbituric acid derivatives were prepared via Knovenagel reaction between aldehydes and (thio)barbituric acid. Using this reagent also pyrano[2,3-d]pyrimidinone(thione) derivatives were synthesized through a three-component reaction between aldehydes, (thio)barbituric and malononitrile. Both reactions are performed in water with good to excellent yields during acceptable reaction times. No organic solvent was used during reaction or separation steps and no extra-purification was exerted. Meanwhile, reusability of taurine was easy and noticeably high.

Green Synthesis of Pyrazol‑chromeno[2,3‑d]pyrimidinones Using SBA-Pr-SO3H as an Efficient Nanocatalyst

Hexagonal mesoporous silica (SBA-15) was prepared and then functionalized by(3-mercaptopropyl)trimethoxysilane. The obtained 3-mercaptopropyl functionalized SBA-15 (SBA-Pr-SH) was then oxidized using H2O2 in methanol under an acidic condition to give sulfonic acid functionalized mesoporous silica (SBA-Pr-SO3H). The latter was characterized using different techniques (including TGA, BET, BJH, CHN, SEM, and TEM) and then used as a catalyst in organic synthesis. In the next step, SBA-Pr-SO3H catalyzed the three-component reaction of pyrazolone, salicylaldehydes, and barbituric acid in water under reflux condition. Through this procedure various pyrazolchromeno[2,3-d]pyrimidinone derivatives were obtained. The reaction conditions were completely green due to the use of water as a solvent and the presence of an environmentally benign catalyst.

Chemistry of new dimethyl-benzo,-1,3,6-oxadiazepine and 1,3,5-triazepine derivatives as anticancer agents

ABSTRACTA series of novel substituted 2,4-dimethyl-benzo[f][1,3,5] triazepine, such as 2-thioxopyrimidinone(4), 2-oxopyridine-3-carbonitrile(6), benzamide(8), N’-(6-oxopyrimidine)benzohydrazide(10), 1-(4-(1,3,4-oxadiazole)thiophene)ethan-one(12), 1-(4-methylthiophene-3-carbonyl)pyrazolidine-dione(14), 1-(4-(pyrazole-carbonyl)-3-methylthiophene)ethanone(16), ethyl dimethylthieno[2,3-b]pyridine-2-carboxylate (18), and 2-thioxo-thieno[2,3-d]pyrimidinone(20) derivatives, were synthesized from 2,4-dimethyl benzo[d] [1,3,6] oxadiazepine (2). The structures of these newly synthesized compounds were established on the basis of their spectral data and elemental analysis. These compounds were also screened for their anti-tumor activities. Some of the prepared compounds showed promising activities for example; benzotriazepine, thienopyrimidine, oxadiazole, and thiophene moiety displayed cytotoxic activity.

Nanoporous Na+-montmorillonite perchloric acid as an efficient heterogeneous catalyst for synthesis of merocyanine dyes based on isoxazolone and barbituric acid

Nanoporous Na+-montmorillonite perchloric acid (MPA) as a novel heterogeneous solid acid catalyst was easily prepared. The physico-chemical properties of the catalyst were analyzed by a variety of techniques including X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), energy dispersive X-ray spectroscopy (EDX), Brunauer-Emmett-Teller (BET) and nitrogen adsorption-desorption measurements, pH analysis and Hammett acidity function. The prepared reagent showed excellent catalytic activity for the green one-pot, three component synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-one, pyrano [2,3-d] pyrimidinone and 5-arylidine barbituric acid derivatives in aqueous media. The remarkable features of the present protocol are availability and low cost of the starting materials, reusability of the catalyst, short reaction times and high yields of the products.

Synthesis, Antibacterial Activity, and Docking Studies of 1,2,3‐triazole‐tagged Thieno[2,3‐d]pyrimidinone Derivatives

Novel (1‐(substituted phenyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl‐2‐(4‐oxo‐5,6,7,8‐tetrahydrobenzo[1,2]thieno[2,3‐d]pyrimidin‐3(4H)‐yl)acetate derivatives were synthesized. All the compounds showed significant antibacterial activity against Gram‐negative (Escherichia coli and Klebsiella pneumonia) and Gram‐positive (Bacillus subtilis and Bacillus cereus) bacteria. Particularly, (1‐(3‐nitrophenyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl‐2‐(4‐oxo‐5,6,7,8‐tetrahydrobenzo[1, 2]thieno[2,3‐d]pyrimidin‐3(4H)‐yl)acetate was found to be most potent against E. coli, K. pneumonia, and B. subtilis with MIC 25 μg/ml. Molecular docking was also performed on purine riboswitch of B. subtilis and thiamine pyrophosphate riboswitch of E. coli.

Serendipitous formation of novel class of dichromeno pyrano pyrimidinone derivatives possessing anti-tubercular activity against M. tuberculosis H37Rv

One pot three-component reaction of salicylaldehyde, barbituric acid, and 4-OH coumarin catalyzed by ionic liquid, 1-(ethylaceto acetate)-1-(2-hydroxyethyl) piperidinium tetrachloroaluminate [EAHEPiPY]+ [AlCl4]− in water resulted into unexpected formation of a novel class of dichromeno pyrano pyrimidinone derivatives. Synthesized compounds exhibited excellent in vitro anti-tubercular activity against M. tuberculosis H37Rv.

Ring Transformation of a 2(3H)‐furanone Derivative into Oxazinone and Pyrimidinone Heterocycles

The conversion of the 2(3H)‐furanone into the oxazinone and pyrimidinone derivatives is studied. A 2‐(furan‐2‐ylmethylene)‐4‐oxo‐4‐phenylbutanoyl azide 3 was synthesized to carry out these conversions through its thermolysis in dry benzene and/or base‐catalyzed decomposition of this azide in the presence of different amines. The structures of all compounds were demonstrated from their spectral data and elemental analyses.

Two Different Green Catalytic Systems for One‐Pot Regioselective and Chemoselective Synthesis of Some Pyrimido[4,5‐d]Pyrimidinone Derivatives in Water

In this work, we have developed green and efficient regioselective and chemoselective syntheses of 5‐aryloyl‐1,3‐dimethyl‐7‐thioxo‐5,6,7,8‐tetrahydropyrimido[4,5‐d]pyrimidine‐2,4(1H,3H)‐dione and 5‐aryloyl‐1,3‐dimethyl‐2,7‐dithioxo‐2,3,5,6,7,8‐hexahydropyrimido[4,5‐d]pyrimidin‐4(1H)‐one derivatives via one‐pot three‐component Biginelli‐like condensation of arylglyoxal monohydrates, N,N‐dimethylbarbituric acid or N,N‐dimethyl‐2‐thiobarbituric acid, and thiourea in water at 50°C. The presence of two different green catalytic systems (ZrOCl2.8H2O and also DABCO) proceeded efficiently to afford the desired products in good‐to‐excellent yields. An aqueous reaction medium, high regioselectivity and chemoselectivity, simple operation and suitable yields of products are the important features of these green protocols.

Structural analysis and antimicrobial activity of 2[1H]-pyrimidinethione/selenone derivatives

Four new crystal structures of sulfur and selenium analogues of 2[1H]-pyrimidinone derivatives were determined with the use of X-ray diffraction method. The molecular geometry and intermolecular interactions of the investigated molecules were analyzed in order to find the structural features and geometrical parameters, which can be responsible for antimicrobial activities. The influence of chalcogen substituents (sulfur and selenium) on the crystal packing was also studied. The main differences in the molecular structures exist in mutual arrangement of two aromatic rings. The intermolecular interactions in all investigated compounds are similar. Furthermore, the in vitro antibacterial and antifungal activities for these compounds were evaluated. Preliminary investigations have identified two highly potent antibacterial compounds containing selenium atom, which display selectivity towards staphylococci and micrococci. This selectivity was not observed for a control compound used as a drug, namely vancomycin. These compounds possess also good antifungal activity. This is the first report of biological activities of 2[1H]-pyrimidineselenone derivatives.

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

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.

ACCESS TO CONVENIENT SYNTHESIS OF OXAZINONE AND PYRIMIDINONE HETEROCYCLES DERIVED FROM 2(3H)-FURANONE

The conversion of the 2(3 H )-furanone into the oxazinone and pyrimidinone derivatives is studied. A 2-(furan-3-ylmethylene)-4-oxo-4-phenylbutanoyl azide 3 was synthesized to carry out these conversions through its thermolysis in dry benzene and/or base-catalyzed decomposition of this azide in the presence of different amines. The structures of all compounds were demonstrated from their spectral data and elemental analyses.

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor.

Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.

A Green, One-Pot Formation of Imidazolone and Pyrimidinone Derivatives Containing a Sulfonyl Group

The synthesis of sulfonyl-imidazolone derivatives via a four-component reaction between sodium arylsulfinates, trichloroacetonitrile, benzylamines and acetylenedicarboxylates in H2O at room temperature is described. When alkyl propiolate was used instead of acetylenedicarboxylates, sulfonyl-pyrimidinone was obtained.

ChemInform Abstract: Reaction of α‐Oxoketenes with 2‐Substituted Benzothiazoles and Benzimidazoles: Synthesis of Benzo[4,5]thiazolo[3,2‐a]pyridinone and N‐(1,3‐Benzothiazol‐2‐yl)‐3‐oxopropanamide Derivatives.

A fast and simple procedure for the synthesis of pyrimidinone derivatives via the cyclocondensation reactions of α-oxoketenes with 2-substituted benzothiazoles have been investigated. Acyl-substituted Meldrum's acids and 1,3-dioxin-4-one derivatives have been used as starting compounds for preparation of α-oxoketenes, which were used in the cycloaddition reactions with (benzothiazol-2-yl)-acetonitrile and (benzimidazol-2-yl)acetonitrile giving good product yields. Also the reaction of (chlorocarbonyl)phenylketene with 2-(1,3-benzothiazol-2-yl)acetonitrile has been investigated.

ChemInform Abstract: Broensted Acidic Ionic Liquid [C3SO3HDoim]HSO4 Catalyzed One‐Pot Three‐Component Biginelli‐Type Reaction: An Efficient and Solvent‐Free Synthesis of Pyrimidinone Derivatives and Its Mechanistic Study.

ChemInformVolume 47, Issue 27 Heterocyclic Compounds ChemInform Abstract: Broensted Acidic Ionic Liquid [C3SO3HDoim]HSO4 Catalyzed One-Pot Three-Component Biginelli-Type Reaction: An Efficient and Solvent-Free Synthesis of Pyrimidinone Derivatives and Its Mechanistic Study. Zhi-Lei Zhou, Zhi-Lei Zhou Sch. Chem. Eng., Nanjing Univ. Sci. Technol., Nanjing 210094, Peop. Rep. ChinaSearch for more papers by this authorPeng-Cheng Wang, Peng-Cheng Wang Sch. Chem. Eng., Nanjing Univ. Sci. Technol., Nanjing 210094, Peop. Rep. ChinaSearch for more papers by this authorMing Lu, Ming Lu Sch. Chem. Eng., Nanjing Univ. Sci. Technol., Nanjing 210094, Peop. Rep. ChinaSearch for more papers by this author Zhi-Lei Zhou, Zhi-Lei Zhou Sch. Chem. Eng., Nanjing Univ. Sci. Technol., Nanjing 210094, Peop. Rep. ChinaSearch for more papers by this authorPeng-Cheng Wang, Peng-Cheng Wang Sch. Chem. Eng., Nanjing Univ. Sci. Technol., Nanjing 210094, Peop. Rep. ChinaSearch for more papers by this authorMing Lu, Ming Lu Sch. Chem. Eng., Nanjing Univ. Sci. Technol., Nanjing 210094, Peop. Rep. ChinaSearch for more papers by this author First published: 16 June 2016 https://doi.org/10.1002/chin.201627190Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume47, Issue27June, 2016 RelatedInformation

Three-component synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles in aqueous medium

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-Fe2O3 nanoparticles (γ-Fe2O3@HAp-Ni2+ NPs) as Lewis acid. The nontoxic nature and easy handling of the catalyst, environmentally friendly and facile work-up procedure, short reaction time, low catalyst loading, and high effectiveness to give products in good to excellent yield are advantages of this approach. Also, γ-Fe2O3@HAp-Ni2+ NPs can be easily recovered and reused for at least six runs.

The first urea‐based ionic liquid‐stabilized magnetic nanoparticles: an efficient catalyst for the synthesis of bis(indolyl)methanes and pyrano[2,3‐d]pyrimidinone derivatives

Urea‐based ionic liquid stabilized on silica‐coated Fe3O4 magnetic nanoparticles, {Fe3O4@SiO2@(CH2)3‐Urea‐SO3H/HCl}, as an unexceptionable and smooth releasing urea fertilizer in alkali soils was synthesized and fully characterized using Fourier transform infrared, UV–visible and energy‐dispersive X‐ray spectroscopies, X‐ray diffraction, scanning and transmission electron microscopies, atomic force microscopy and thermogravimetric analysis. The nanostructure catalyst as a novel, green and efficient catalyst was applied for the synthesis of bis(indolyl)methane derivatives via the condensation reaction between 2‐methylindole and aldehydes at room temperature under solvent‐free conditions. Also, pyrano[2,3‐d]pyrimidinone derivatives were prepared in the presence of the nanomagnetic urea‐based catalyst by the one‐pot three‐component condensation reaction of 1,3‐dimethylbarbituric acid, aldehydes and malononitrile under solvent‐free conditions at 60 °C. To the best of our knowledge, this is the first report of the synthesis of urea‐based ionic liquid stabilized on silica‐coated Fe3O4 magnetic nanoparticles. So the present work can open up a new and promising insight in the course of rational design, synthesis and applications of task‐specific fertilizer‐based nanomagnetic ionic liquids with desirable properties as unexceptionable substances for sustainable processes. Copyright © 2016 John Wiley & Sons, Ltd.

ChemInform Abstract: Base‐Catalyzed One‐Pot Tandem Reaction: An Effective Strategy for the Synthesis of Pyrazolo[3,4‐d]pyrimidinone Derivatives.

AbstractThe reactions from hydrazines [e.g. (I)], methylenemalononitriles [e.g. (II)] and aldehydes [e.g. (IV)] give pyrazolopyrimidinone [e.g. (V)] in good yields via a nucleophilic addition/cyclization/aromatization/nucleophilic addition/Dimroth rearrangement/dehydroaromatization sequence.

Reaction of α-oxoketenes with 2-substituted benzothiazoles and benzimidazoles: synthesis of benzo[4,5]thiazolo[3,2-a]pyridinone and N-(1,3-benzothiazol-2-yl)-3-oxopropanamide derivatives

A fast and simple procedure for the synthesis of pyrimidinone derivatives via the cyclocondensation reactions of α-oxoketenes with 2-substituted benzothiazoles have been investigated. Acyl-substituted Meldrum's acids and 1,3-dioxin-4-one derivatives have been used as starting compounds for preparation of α-oxoketenes, which were used in the cycloaddition reactions with (benzothiazol-2-yl)-acetonitrile and (benzimidazol-2-yl)acetonitrile giving good product yields. Also the reaction of (chlorocarbonyl)phenylketene with 2-(1,3-benzothiazol-2-yl)acetonitrile has been investigated.