27402-31-9

Usage

InChI:InChI=1/C11H7ClN2O3/c12-7-3-1-6(2-4-7)5-8-9(15)13-11(17)14-10(8)16/h1-5H,(H2,13,14,15,16,17)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 1001318-05-3 3-(4-chlorophenyl)-2-phenyl-3,3a-dihydro-2H-pyrazolo[3,4-d]pyrimidine-4,6-(5H,7H)-dione 
• 1001318-29-1 5-(4-chlorophenyl)-7-hydrazinopyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione 
• 1001318-17-7 3-(4-chlorophenyl)-3,3a-dihydroisoxazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione 
• 1159509-25-7 C₁₇H₉ClN₂O₅ 
• 1159509-27-9 C₁₇H₉ClN₂O₅ 
• 1210058-07-3 10-(4-chlorophenyl)-1,3,5,6,8,10-hexahydropyrido[3,2-d:6,5-d']dipyrimidine-2,4,7,9-tetrone 
• 1210058-02-8 10-(4-chlorophenyl)-1,3,6,8-tetrahydropyrido[3,2-d:6,5-d']dipyrimidine-2,4,7,9-tetrone 
• 1268160-65-1 2-amino-4-(4-chlorophenyl)-6-(piperidin-1-yl)pyridine-3,5-dicarbonitrile 
• 15875-54-4 2-(4-chlorobenzylidene)-2H-indene-1,3-dione 
• 15782-02-2 9-(4-chlorophenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydroxanthene-1,8-dione 
• 1289444-66-1 5-chloro-5-(4-chlorobenzyl)barbituric acid 
• 1753-47-5 5-(4-dimethylaminobenzylidene)barbituric acid 
• 130517-96-3 N-[(1E)-(4-chlorophenyl)methylidene]benzenemethanamine 
• 104-88-1 4-chlorobenzaldehyde 

Relevant academic research and scientific papers

Low transition temperature mixtures prompted one-pot synthesis of 5, 10 dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dione derivatives

Abstract: An efficient green protocol has been investigated for the synthesis of pyrimido[4,5-b]quinolines derivatives via one-pot three-component condensation of 4-chloro aniline, aromatic aldehyde and barbituric acid using low transition temperature mixtures as new generation and sustainable solvents. The process was accomplished with the use of greener and recyclable reaction media, simple methodology, easy workup procedures and no chromatographic purification with high yield. This new approach is expected to discover some significance in combinatorial synthesis of biologically active scaffolds.

Water-prompted synthesis of alkyl nitrile derivatives via Knoevenagel condensation and Michael addition reaction

A straightforward and efficient method for the synthesis of nitriles or β-cyanocarbonyls via Knoevenagel condensation and Michael addition reaction of a barbituric acid, aldehyde and sodium cyanide in water without using any catalyst or activation at 70 °C is reported. The Royal Society of Chemistry.

One-pot three component cascade synthesis of fused ring quinazoline-2,4-dione derivatives employing heterocyclic ketene aminals as a versatile synthone

One-pot three component cascade protocol for the synthesis of quinazoline-2,4-dione derivatives was designed and a series of twenty fused ring quinazoline-2,4-dione derivatives 11a-11j and 12a-12j were synthesized by the reaction of heterocyclic ketene am

[2,2'-Bipyridine]-1,1'-diium perchlorate as a new and efficient dicationic organic salt for the promotion of the synthesis of bis(4-hydroxycoumarin), 5-arylidene barbituric acid and pyrano[2,3-d]pyrimidinone derivatives in water

A simple and convenient procedure for the synthesis of 5-arylidene barbituric acid, pyrano[2,3-d]pyrimidinone and 4-hydroxycoumarin derivatives using [H2-BiPyr][ClO4]2 as an efficient, easily producible and recyclable promoter is reported. All reactions were performed under mild conditions, and the requested products were obtained during the acceptable reaction times in high to excellent yields.

Nanosized calcined mixed oxides-supported alkali metal (K2O/Al2O3–CaO) as solid base catalyst: preparation and investigation of its catalytic efficiency in the synthesis of benzylidene malononitriles/barbiturates and in pyrano[2,3-d]pyrimidines

Potassium impregnated over mixed oxides (K2O/Al2O3–CaO) as solid base catalyst was synthesized and characterized by various techniques such as FTIR, TGA, XRD, TEM, SAED, SEM and XPS. It efficiently catalyzed the one-pot Knoevenagel/Michael condensation to form derivatives of pyrano[2,3-d]pyrimidine and benzylidene malononitrile derivatives, benzylidene barbituric acid derivatives by Knoevenagel condensation which were isolated and characterized by 1H-NMR and 13C-NMR. The catalyst was recyclable up to five runs without any significant loss in activity. Graphical abstract: [Figure not available: see fulltext.]

A method for rapid synthesis of 18Olabeled aldehyde compounds

The present invention discloses a method for rapid synthesis of 18O labeled aldehyde compounds, first the aldehyde compound and barbituric acid was added to ethanol, reacted at 40 ~ 60 ° C for 10 to 12 h, to obtain precipitation, cooled to room

Knoevenagel condensation in aqueous media promoted by 2,2′-bipyridinium dihydrogen phosphate as a green efficient catalyst

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.

Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push–pull electronic systems: Experimental and quantum chemical study

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.

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

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.

Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations

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.