5-arylidenebarbituric Acids Research Articles

Succinimidium Perchlorate as a Novel and Efficient Brönsted Acidic Ionic Liquid Promoter for the Synthesis of 5-arylidene Barbituric Acid and pyrano[2,3-d] Pyrimidinone Derivatives

Introduction:: In this article, succinimidinium perchlorate as a new acidic ionic liquid catalyst was prepared and used to synthesize 5-arylidene barbituric acid and pyrano[2,3-d]pyrimidinone derivatives. Method:: These two derivatives of barbituric acid have a variety of useful properties. Result:: The advantages of this reagent were high yields, high efficiency, short reaction times, easy performance, easy work-up and reusability. Conclusion:: Succinimidinium perchlorate, which was made for the first time in this project, was identified with different methods, including FT-IR, 1H NMR, 13C NMR and mass spectroscopic techniques

Structural Analysis of Calcium Oxide Derived from Waste Egg’s Shells and their Application for Knoevenagel Condensation Reactions

The present study demonstrates the simple and easy synthesis of calcium oxide (CaO) from waste egg’s shells. Fine egg’s shells powder were calcinated at 500, 700 and 800 ºC. The structural and morphological evaluation of calcium oxide derived from waste egg’s shell were examined by using XRD, FT-IR, SEM, EDS and TEM techniques. The sintered calcium oxide was used as heterogeneous catalyst for the synthesis of 5-arylidene malononitrile and 5-arylidene barbituric acid derivatives by the condensation of various aromatic aldehyde and active methylene compounds via Knoevenagel condensations reaction under ultrasound irradiation method. The reaction completed within a very short reaction time with high yields of product. The present method describes easy synthesis of calcium oxide catalyst from the waste egg’s shells, short reaction times, simple product isolation, excellent yield and reusability of the catalyst.

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

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

Adsorpcijski i inhibitorski uticaj 5-[4-(dimetilamino) benziliden] - 1,3-dimetilbarbiturne kiseline na koroziju ugljeničnog čelika u molarnom rastvoru hlorovodonične kiseline

The inhibiting impact of ecofriendly 5-[4-(dimethylamino) benzylidene]-1,3-dimethylbarbituric acid in 1 M HCl on the corrosion for carbon steel has been examined via "weight loss (WL) method, potentiodynamic polarization (PP), electrochemical impedance spectroscopy (EIS), electrochemical frequency modulation (EFM) tests". The attained outcomes exhibit that the investigated compound is excellent inhibitor and its inhibition efficiency (%IE) rises by raising concentration and decreases by raising the temperature. The adsorption of 5-arylidene barbituric acid on the surface of C-steel follows Langmuir isotherm. The adsorption process of the investigated compound is spontaneous and considered as of chemisorption and physisorption type. PP curves revealed that the 5-arylidene barbituric acid derivative is mixed-type inhibitor. Moreover, EIS results confirmed the adsorption of the investigated compound on C-steel surface via increasing on charge transfer resistance (R ct). The IE% of this inhibitor reached to 86.9% at concentration 21×10-6 M according to PP method. Finally, the experimental and theoretical results are in good harmony.

5-Arylidene-1,3-dialkylbarbituric acid derivatives as efficient corrosion inhibitors for carbon steel in molar hydrochloric acid solution.

The inhibiting impact of two ecofriendly 5-arylidene barbituric acid derivatives (5-ABA), namely 5-(3,4-dimethoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (inhibitor I, 3a) and 5-(3,4-dimethoxybenzylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (inhibitor II, 3b), in 1 M HCl on the corrosion of carbon steel has been examined via the weight loss (WL) method, potentiodynamic polarization (PP), electrochemical impedance spectroscopy (EIS), and electrochemical frequency modulation (EFM) tests. In addition, DFT calculations and MC simulations were used to study the relationship between the inhibitor structure and its inhibition performance. The attained outcomes exhibit that the investigated compounds are excellent inhibitors and their inhibition efficiency (%IE) increases with the increase in the concentration and temperature. The adsorption of 5-arylidene barbituric acid on the C-steel surface was found to follow the Langmuir adsorption isotherm. The adsorption process of the investigated compounds is spontaneous and considered as the chemisorption type. The PP curves revealed that 5-arylidene barbituric acid derivatives are mixed-type inhibitors. Moreover, the EIS results confirmed the adsorption of 5-arylidene barbituric acid derivatives on the C-steel surface by increasing the charge transfer resistance (Rct) values. The %IE of the inhibitors (II & I) reached 92.8% and 86.6% at a concentration of 21 × 10−6 M, according to the WL method. The surface analysis of the C-steel surface was confirmed by scanning electron microscopy and energy dispersive X-ray techniques. Finally, the experimental and theoretical results are in good agreement.

Docking and Antibacterial Activity of Novel Nontoxic 5-Arylidenepyrimidine-Triones as Inhibitors of NDM-1 and MetAP-1

Background: Antibiotic resistance, which occurs through the action of metallo-β-lactamases (NDM-1), is a serious problem in the treatment of infectious diseases. Therefore, the discovery of new NDM-1 inhibitors and promising antibacterial agents as inhibitors of alternative targets (MetAP-1) is important. Method & results: In this study, a virtual library of 5-arylidene barbituric acids was created and molecular docking was performed for identification of novel possible inhibitors of NDM-1 and MetAP-1. Antibacterial activity (agar well-diffusion assay) and cytotoxicity (alamarBlue assay) of perspective compounds were evaluated. Pharmacokinetic profiles and molecular properties were predicted. Conclusion: We have identified possible novel inhibitors of NDM-1 and MetAP-1 with bacteriostatic activity, most of which are not cytotoxic and have potential excellent drug-likeness properties.

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.

Introduction of Agar-Entrapping as a Novel Strategy to Improve the Catalytic Activity of Moisture-Absorbing Acidic Ionic Liquids: A Case Study in the Synthesis of 5-Arylidene Barbituric Acids and Pyrano[2,3-d]Pyrimidinones

In this article, to improve the detrimental character of ionic liquids, called moisture absorbing, agar-trapping is introduced as an affordable and straightforward protocol. Using inexpensive biopolymer, agar, as a trapper is a brilliant advantage of the method led to an environmentally sustainable development. Moreover, to show the effect of this method, the catalytic ability of a prepared agar-trapped acidic ionic liquid and its free form was experimentally compared in the synthesis of barbituric and thiobarbituric acid derivatives. In the presence of the entrapped catalyst and under the optimized conditions the products were obtained in high yields during short reactions time.

Facile catalyst-free synthesis of perfluoroalkylated cis-spiropyrimidine-5,1′-quinolizines and pyrano[2,3-d]pyrimidines

A simple, catalyst-free, straightforward, and highly efficient synthesis of pharmaceutically interesting diverse perfluoroalkylated cis-spiropyrimidine-5,1′-quinolizines and pyrano[2,3-d]pyrimidines has been developed based on a three component reaction between 5-arylidenebarbituric acids 1, methyl perfluoroalk-2-ynoates 2, and pyridines 3 in MeCN at -10 °C or 65 °C. The salient features of this protocol are mild reaction conditions, use of no catalyst, short reaction time, a simple operation and good to excellent yields.

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

We report synthesis of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide ([TPPHSP]Br) as a reusable green Bronsted-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.

Effect of Reaction Parameters on the Synthesis of 5-Arylidene Barbituric Acid Derivatives in Ball Mills

The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (νrot), milling ball diameter (dMB), milling ball filling degree (ΦMB), and beaker size had obvious influences on yield. It was found that higher νrot, lower dMB, milling beakers with larger diameter, and a ΦMB of ∼0.3 are advantageous for the reaction. Furthermore, the influence of the type of mill was investigated, including reactions performed in different planetary and mixer ball mills, in a stirred media mill, and with a mortar mill. Comparisons with the other solvent-free synthetic routes showed that ball milling is an effective way of performing the reaction with low energy intensity.

Colorimetric detection of fluoride ion by 5-arylidenebarbituric acids: dual interaction mode for fluoride ion with single receptor

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 (1)H-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.

Synthesis of fused uracils: pyrano[2,3-d]pyrimidines and 1,4-bis(pyrano[2,3-d]pyrimidinyl)benzenes by domino Knoevenagel/Diels-Alder reactions.

Knoevenagel condensation of barbituric acids with aromatic aldehydes containing one or two formyl groups was carried out. 5-Arylidenebarbituric acids underwent smooth hetero-Diels-Alder (HDA) reactions with enol ethers to afford cis and trans diastereoisomers of pyrano[2,3-d]pyrimidine-2,4-diones and 5,5′-(1,4-phenylene)bis[2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione] derivatives in excellent yields (75–88 %). Syntheses were realized by Knoevenagel condensation and HDA reaction in four different reaction conditions: Knoevenagel condensation in water and Diels-Alder reaction in methylene chloride solution, Knoevenagel condensation in water and Diels-Alder reaction without solvent, three-component one-pot reaction in methylene chloride solution, or three-component one-pot reaction in water. All reactions were carried out without catalyst at room temperature. The reactions of malononitrile with Knoevenagel condensation products of barbituric acids and heteroaromatic aldehydes or terephthalaldehyde were examined and did not provide corresponding pyranopyrimidines.Graphical .

SiO2·12WO3·24H2O: a Highly Efficient Catalyst for the Synthesis of 5-Arylidene Barbituric Acid in the Presence of Water

The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO2·12WO3·24H2O 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.

Graphical Abstracts

Graphical Section

New approach to the construction of the ABCD tetracyclic 8,15,17-triaza-D-homogonane skeleton by the [3+3]cyclocondensation of 1-methyl-3,4-dihydroisoquinolines with 5-arylidenebarbituric acids

New approach to the construction of the ABCD tetracyclic 8,15,17-triaza-D-homogonane skeleton by the [3+3]cyclocondensation of 1-methyl-3,4-dihydroisoquinolines with 5-arylidenebarbituric acids

Mild oxidation of allylic and benzylic alcohols with 5-arylidene barbituric acid derivatives as a model of redox coenzymes.

Under neutral conditions 5-arylidene 1, 3-dimethylbarbituric acid effectively oxidizes allylic and benzylic alcohols to the corresponding carbonyl compounds.There is a close relationship between oxidizing ability and electron density on the aromatic ring. The mechanism of this oxidation involves hydride transfer from the alcohol.

Investigations in the series of heterocycles. 53. Mass spectra of 5-arylidenebarbituric acids and their 2-thio- and 2-seleno-analogs

The mass spectra of 5-arylidenebarbituric acids, their 2-thio- and 2-seleno-analogs, barbituric, 2-thio- and 2-selenobarbituric acid, as well as selenourea, were obtained. The molecular ions of these compounds, as a rule, the main ones in intensity, may break down along several pathways, the ratio of which depends substantially on the nature of the atom bound to the carbon atom in the 2-position of the pyrimidine ring. The influence of substituents in the benzene ring on the direction of decomposition of the molecular ions is negligible.

Immunosuppressive activity of 5-arylidenebarbituric acid and arylideniminoethanesulfonic acid derivatives

The 5-arylidenebarbituric acids were obtained by a known method [i] and were colored substances, poorly soluble in normal organic solvents (see Table i). UV spectra for the 5arylidenebarbituric acids have, in addition to characteristic absorption for them in the range 245-255 nm, intensive absorption at 380-420 nm. A bathochromic shift to longer wave lengths in observed on increasing the conjugation chain through the aldehyde component.