In this investigation, we successfully synthesized fused pyridonaphthyridines, a newly identified class of fused heterocyclic compounds, through an efficient multicomponent reaction. The methodology involved utilizing 3-(2-hydroxyphenyl)-3-iminopropanamide, 2-(1,3-diimino-1,3-dihydro-2H-inden-2-ylidene) malononitrile, alkyl bromides, and activated acetylenic derivatives within an aqueous medium at ambient temperature. Notably, the process was facilitated by a reusable catalyst composed of Ag/Fe3O4@GO. The newly synthesized compounds were subsequently evaluated for their antiproliferative potential against MCF-7 breast cancer and HCT-15 colon cancer cell lines using the Sulfo-rhodamine B (SRB) assay, along with their antioxidant capabilities. Among the compounds tested, derivatives 5c and 5 g demonstrated notably superior antiproliferative activity relative to their counterparts. To further explore their interaction with biological macromolecules, these two compounds underwent UV-Vis spectral analysis to determine their binding affinities to DNA and bovine serum albumin (BSA). The results revealed affinity constants of K5c-DNA = 7.32 x 10(3) M-1, K5g-DNA = 2.09 x 104 M-1, K5c-BSA = 5.32 x 104 M-1, and K5g-BSA = 8.24 x 104 M-1, respectively. The outcomes of this study could provide novel insights into the relationship between the chemical structure of these pyridonaphthyridine analogs and their capacity to inhibit cancer cell proliferation.
Coumarin derivatives represent an important class of heterocyclic compounds with broad applications in pharmaceuticals, agrochemicals, and functional materials. Consequently, there is ongoing interest in developing efficient and eco-friendly catalytic systems for their synthesis. In this study, a new heterogeneous magnetic nanocatalyst (Fe3O4@L-Arginine/La2O3 magnetic nanoclusters) was prepared via a simple co-precipitation method using FeCl2.4H(2)O, FeCl3.6H(2)O, L-Arginine, and La(NO3)(3).6H(2)O in the presence of NaOH under a nitrogen atmosphere. The prepared compound was characterized by FT-IR, XRD, Raman, TEM, FE-SEM, EDX, TGA, VSM, and ICP-AES analyses. Fe3O4@L-Arginine/La2O3 magnetic nanoclusters exhibited good catalytic activity and were found to condense via the Pechmann reaction to form coumarin derivatives with high yields in short reaction times at mild conditions, using ethanol as a green solvent and a low catalyst concentration (5 mol%). This system has obvious benefits, which are compared to earlier reported catalysts, as highlighted in the fact that there is simplicity in magnetic recovery, good structural integrity, negligible metal leaching, and high recyclability with a low loss of activity. The synergistic effect of the active sites of the La2O3 acid with the multifunctional L-Arginine surface groups is considered to be the reason for the high catalytic efficiency of the reaction substrates. In general, this publication presents a strong, eco-friendly, and reusable magnetic nanocatalyst that has a tremendous value in reusable coumarin synthesis.
ABSTRACT This manuscript elucidates a methodology for the synthesis of thiazinonaphthyridine employing benzaldehydes, malononitrile, thiophenol, acetylenic esters, and isothiocyanates. The synthetic process is conducted at ambient temperature devoid of solvent utilization, employing a recyclable catalyst designated as SiO 2 /Fe 3 O 4 @MWCNTs, which yields favorable results. It is imperative to note that the exceptional efficacy of the synthesized nanocatalyst was achieved through the utilization of an aqueous extract derived from the leaves of Petasites hybridus , which was employed in these reactions multiple times to ascertain the reusability of the nanocatalyst. The antioxidant properties of the newly synthesized thiazinonaphthyridine can be attributed to the presence of the NH group, which was assessed through two methodologies known as diphenyl‐picrylhydrazine (DPPH) radical trapping and the Ferric ions (Fe 3+ ) reducing potential (FRAP) assay. Compound 6b exhibited superior efficacy when evaluated against BHT and TBHQ among the thiazinonaphthyridine derivatives 6a–6d that were analyzed. Furthermore, the antimicrobial efficacy of the newly produced thiazinonaphthyridine was examined through a disk diffusion method involving two distinct strains of Gram‐negative and Gram‐positive bacteria from which thiazinonaphthyridine derivatives 6a , 6d , 6e , 6g , and 6j exhibit significant antibacterial activity against Escherichia coli , presumably attributable to the considerable breadth of the zone of inhibition. The methodology employed for the synthesis of thiazinonaphthyridine derivatives presents advantages such as reduced reaction times, high product yields, and the feasibility of separating the catalyst from the products through a straightforward procedure.
In this study, the metal organic framework (MOF)-based heterogeneous magnetic nanocatalyst of Fe3O4/NH2MIL101(Fe)-SO3H was designed and synthesized for the first time, and was fully analyzed and confirmed by microscopic methods including FE-SEM and TEM and also spectroscopic methods including FT-IR, EDX and XRD. In addition, VSM and TGA/DTG analysis were performed on it. Subsequently, in the presence of this nanocatalyst and through a single-step, three-component condensation of malononitrile, barbituric acid, and aldehyde, a series of pyrano[2,3-d]pyrimidine derivatives were synthesized under solvent-free conditions and with desirable yields. In another part of this project, the biological properties (including anticancer activity, hemolytic effect, and antibacterial activity) of the synthesized derivatives were evaluated and compared. All of these derivatives, despite their weak hemolytic effects, showed good anticancer activity against human breast cancer cells (MCF-7 cell line). They also inhibited the growth of E. coli and S. aureus bacteria to a good extent. Finally, the structural and electronic properties of the products were investigated using density functional theory (DFT) at the B3LYP/ 6-31G** level in the gas phase. For this purpose, all the predicted reactants and products were geometrically optimized and then thermodynamic and frequency calculations were performed to evaluate their stability and reactivity. The Gibbs free energies of formation (Delta GF) were calculated to evaluate the thermodynamic desirability of the reactions. Also, frontier molecular orbital (FMO) analysis, energy gap, and chemical stability were investigated. In addition, electronic descriptors including chemical potential, hardness, and electrophilicity index were evaluated to further understand the electronic behavior of the products. All the structures showed positive vibrational frequencies, confirming their thermodynamic stability. The results show that the selected products, especially product 4c, have favorable stability and have the potential for further exploration in materials and applications.
Heteroarenes bearing a difluoromethyl (CF2H) group have emerged as important structural motifs in pharmaceuticals, agrochemicals, and materials science, as the CF2H unit can fine-tune lipophilicity, strengthen biological interactions, and enhance metabolic stability. Among the available synthetic approaches, direct C-H difluoromethylation of heteroaromatic frameworks stands out as an efficient, step-economical, and atom-economical strategy. In this review, we highlight the most significant advances and developments in the direct C-H difluoromethylation of heteroaromatic compounds reported up to the end of 2025. Catalyst-free reactions are discussed first, followed by metal-catalyzed/mediated and photoredox-catalyzed transformations. Finally, electrocatalytic approaches are covered at the end of the review.
In this research, furochromene derivatives were synthesized using multicomponent reactions of dihydroxyacetophenone, isopropenylacetylene, aldehydes and 1,3-dicarbonyl compounds in aqueous media at room temperature in the presence of bio-Fe3O4/SiO2 magnetic nanoparticles (MNPs). The catalytic activity of the bio-Fe3O4/SiO2 was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water under mild conditions. The results indicated that the biosynthesized Fe3O4/SiO2 MNPs exhibited high catalytic activity, enabling the removal of organic pollutants within a few seconds. To determine the antioxidant activity of the synthesized furochromenes, diphenylpicrylhydrazine (DPPH) radical scavenging assays were applied. A further evaluation of the antibacterial activity of the generated compounds was carried out in a methodical manner by employing the disk diffusion technique using two distinct strains of Gram-negative bacteria as well as Gram-positive bacteria. The synthesis approach that was applied for the development of furochromenes was marked by a confluence of good properties. One of these characteristics was the ability to recover the catalyst from the reaction environment with an external magnet. Other characteristics included faster reaction kinetics and greater product yields.
This paper presents a proper and potent method for the direct preparation of a series of structurally intriguing and pharmacologically relevant spirooxindole-fused quinazoline derivatives via a rapid sonochemical treatment in water at room temperature. Consequently, several factors, including ultrasonication strength and time spent, diverse solvents, and catalysts, were examined to get the best process conditions. This procedure is characterized by the utilization of efficient treatment with ultrasound as an alternate source of energy, water as an eco-friendly solvent, and Cu/ZnO-graphene oxide nanocomposite (Cu/ZnO-GO) as a heterogeneous reusable catalyst (for at least 4 times cycles), alongside its straightforward operation, brief reaction time (20 min), and high product yields (92–97%). Several obtained products were also studied for their antioxidant and antibacterial properties. This study indicates that, amongst the four test compounds, 4 h showed highest antioxidant activity with IC50 at 64.5 µg/mL, in comparison to those of the standard butylated hydroxytoluene (BHT) and 2-tertbutylhydroquinone (TBHQ) at 57.1 and 61.4 µg/mL respectively for the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging. The antibacterial activity test of the selected products was showed moderate to high inhibitory effects against both Gram-positive and Gram-negative bacteria.
This paper presents a proper and potent method for the direct preparation of a series of structurally intriguing and pharmacologically relevant spirooxindole-fused quinazoline derivatives via a rapid sonochemical treatment in water at room temperature. Consequently, several factors, including ultrasonication strength and time spent, diverse solvents, and catalysts, were examined to get the best process conditions. This procedure is characterized by the utilization of efficient treatment with ultrasound as an alternate source of energy, water as an eco-friendly solvent, and Cu/ZnO-graphene oxide nanocomposite (Cu/ZnO-GO) as a heterogeneous reusable catalyst, alongside its straightforward operation, catalyst reusability, brief reaction time, and high product yields. Several obtained products were also studied for their antioxidant and antibacterial properties. Favorable outcomes were achieved in both instances of antioxidant and antibacterial activity.
In this research, novel derivatives of imidazopyrimidine with a high level of efficiency were synthesized using Fe3O4@SiO2/CuO MNCs employing multicomponent reactions including vinylidene aldehydes, ethyl 2-amino-4-dioxo-4-arylbutanoates, alkyl bromides, thiourea, and ethyl bromopyruvate in water at room temperature. The produced compounds exhibit antioxidant activity as a result of the evaluation processes conducted on their NH group. Furthermore, an evaluation was performed on the antibacterial effectiveness of newly created pyridines using a disk diffusion technique, utilizing two different strains of Gram-negative bacteria. Significantly, the substances that were evaluated showed inhibitory effects on the development of Gram-positive bacteria as well. This method has several benefits, including quick response times, high product yields, and easy separation of catalyst and product using simple procedures.
The efficient synthesis of high-yield organic compounds remains a central challenge in the field of synthetic chemistry. In the present study, new chromenonaphthyridine derivatives were synthesized by 4-aminocumarin, indenylidenemalononitrile, ammonium acetate, alkyl bromides, and activated acetylenic derivatives within an aqueous medium at ambient temperature through an efficient multicomponent reaction in the presence of Fe3O4@SiO2/CuO as a potential and eco-friendly heterogeneous catalyst. Comprehensive characterization techniques, including SEM, EDS, TEM, XPS, BET, FT-IR, VSM, and XRD, were employed for the prepared catalyst. The obtained results confirmed the successful preparation and structural integrity of the nanocatalyst. The novel synthesized compounds were subsequently evaluated for their antiproliferative potential against MCF-7 breast cancer and HCT-15 colon cancer cell lines using the Sulforhodamine B (SRB) assay, along with their antioxidant capabilities. Among the compounds tested, derivatives 6c and 6g demonstrated notably superior antiproliferative activity relative to their counterparts. To further explore their interaction with biological macromolecules, these two compounds underwent UV-Vis spectral analysis to determine their binding affinities to DNA and bovine serum albumin (BSA). The outcomes of this study could provide novel insights into the relationship between the chemical structure of these chromenonaphthyridine analogs and their capacity to inhibit cancer cell proliferation. The synthesis of chromenonaphthyridines demonstrated a range of advantageous traits, including fast reaction, high yields of the end product, and easy isolation of the catalyst and product from the reaction mixture. Furthermore, the reaction mechanism was illustrated concerning the total energy of the reactant, intermediates, and product, and the structural parameters were analyzed.
In this investigation, we successfully synthesized a fused pyridonaphthyridine, a newly identified class of fused heterocyclic compounds, through an efficient multicomponent reaction. The methodology involved utilizing 1-aminonaphthalene, 2-(1,3-diimino-1,3-dihydro-2H-inden-2-ylidene)malononitrile, alkyl bromides and activated acetylenic derivatives within an aqueous medium at ambient temperature. Notably, the process was facilitated by a reusable catalyst composed of Fe3O4/SiO2/CuO. The antioxidant activity of the synthesized compounds, which could be attributed to the naphthyridine core, was measured by two procedures: DPPH and FRAP. The compound 5a showed the best antioxidant activity relative to other compounds. Additionally, a theoretical study was conducted using density functional theory (DFT) with the B3LYP functional in conjunction with the 6-311G(d,p) basis set to investigate the electronic structures, geometries, and reactivity properties of the molecular compounds. Results revealed that compound 5e showed remarkable reactivity due to its lower energy gap and higher electrophilicity. Furthermore, density functional theory calculations were used to visualize the images of HOMO and LUMO orbitals.
In this investigation, we synthesized pyridonaphthyridines, as a new class of fused heterocyclic compounds, through an efficient multicomponent reaction.
In this review, we spotlight the methodologies for the direct synthesis of β-halo nitroalkanes and nitroalkenes from the corresponding unsaturated hydrocarbons through vicinal halo-nitration strategies. The review is organized into two main sections: halo-nitration of alkenes and halo-nitration of alkynes. Both seminal works and recent advancements are discussed, with a particular emphasis on the mechanistic aspects of the reactions.
ABSTRACT This study synthesized 1,2,4‐triazines, a novel class of derivatives, with a high efficiency using a multicomponent reaction. The reaction involved oxoindolinylidene malononitrile, ethyl 2‐arylamino‐4‐dioxo‐4‐arylbutanoates, and hydrazonoyl chlorides in an aqueous solution at room temperature. The reaction was facilitated by the presence of Ag/Fe 3 O 4 @MWCNTs MNCs. This study examines the antioxidant properties of 1,2,4‐triazine in addition to the other research undertaken in this work. Using the MTT test, the cytotoxic properties of all the produced compounds were assessed in vitro against cancer cell lines (MCF‐7 and A549) and normal cell lines (BEAS‐2B). It was discovered that the most effective cytotoxic agent, doxorubicin like in its lack of selectivity, was Derivative 4e . On the other hand, Compound 4b might be regarded as an equipotent molecule with greater selectivity in relation to doxorubicin. The production process of 1,2,4‐triazine demonstrated several advantageous features, including rapid reactions, high yields of the final product, and straightforward separation of the catalyst and product from the reaction mixture.
Direct vicinal sulfonylative difunctionalization of simple alkenes represents a powerful strategy for the rapid assembly of β-functionalized sulfones from simple starting materials. In this context, the direct sulfonyloximation of alkene substrates has recently received much attention from the chemical community owing to important applications of α-sulfonyl ketoxime products in organic synthesis. This review provides an overview of recent research on the titled reactions, with an emphasis on the reaction patterns and mechanisms. Literature has been surveyed until the end of 2024.
A novel multicomponent method was utilized to attain high yields in the synthesis of new cyclopenta[b]pyridine derivatives. The procedure utilized vinilydene Meldrum’s acid, ethyl 2-amino-4-dioxo-4-arylbutanoates, activated acetylenic compounds, and primary amines. The operation was performed at ambient temperature and in the presence of water. This technique has numerous advantages, such as elevated product yields, rapid reaction times, and uncomplicated product separation methods. The antioxidant activity of the newly synthesized compounds is ascribed to their NH group, which has undergone two testing procedures. The antibacterial efficacy of the synthesized cyclopenta[b]pyridines was evaluated by a disc diffusion method, utilizing two strains of Gram-negative bacteria. These compounds were also discovered to inhibit the growth of Gram-positive bacteria.
This study focused on investigating the synthesis of new spiropyrrole derivatives with high yields. The two nanocatalyst CuO/ZnO@Graphen Oxide nanocomposites (CuO/ZnO@GO NCs) and Ag/CuO/ZnO@Graphen Oxide (Ag@CuO/ZnO@GO NCs) were employed in a multicomponent reaction at room temperature to synthesize new compounds. The reaction involved isatins, N-alkyl isatins, and ninhydrin as activated carbonyl compounds, ammonium acetate, ethyl 2-arylamino-4-dioxo-4-arylbutanoates, hydrazonoyl chloride, or ethylbromopyruvate in water. Also, the catalytic activity of the green synthesized CuO/ZnO@GO and Ag@CuO/ZnO@GO was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the biosynthesized MNCs have very high and effective catalytic activity for organic pollutants within a few seconds. The newly synthesized spiro compounds demonstrate antioxidant activity as a result of two assessment processes conducted by its NH group. In addition, the antibacterial activity of newly created spiro compounds was assessed using a disk distribution method, involving two types of Gram-negative bacteria. These compounds were found to limit the growth of Gram-positive bacteria as well. Also, to better understand the reaction mechanism, density functional theory (DFT)-based quantum chemical methods have been applied. The advantages of this technology encompass rapid response times, high product yields, and uncomplicated catalyst and product separation via simple procedures.
A unique deep eutectic solvent solution was created by combining choline chloride with 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol). In this article, we discussed the synthesis of thiazolo[3,2-a]pyrimidine which utilized environmentally friendly solvent and SiO2/Fe3O4@GO as a reusable catalyst, aldehydes, ethyl acetoacetate, thiourea, and alkyl bromas at room temperature in high yields. Using a water extract from the rhizome of Petasites hybridus for the production of SiO2/Fe3O4@GO is an environmentally acceptable production method which is also a mild base that is used into the manufacturing process. Additionally, diphenyl-picrylhydrazine (DPPH) and ferric reduction tests will be utilized in order to trap radicals in the thiazolo[3,2-a]pyrimidine that has been produced and evaluate the antioxidant characteristics of the compound of interest. The effectiveness of a wide variety of thiazolo[3,2-a]pyrimidine derivatives as antibacterial agents was evaluated by employing both Gram-positive and Gram-negative bacteria, as well as the disk diffusion method. It was determined, on the basis of the findings, that the thiazolo[3,2-a]pyrimidine that was produced was particularly effective in inhibiting the development of bacteria. Through the utilization of this robust technique, numerous enhancements can be achieved in the synthesis of novel thiazolo[3,2-a]pyrimidine. In addition to these enhancements, the reaction times have been reduced, the product yields have been improved, and the catalyst extraction from the byproducts has been simplified.
This work investigated the use of a complex technique including isatoic anhydrides, alpha-haloketones, electron-deficient acetylenic compounds, ammonium acetate, and isothiocyanates in a water-based solution at normal room temperature in the presence of SiO2/Fe3O4@Graphene Oxide. The goal was to generate novel thiazinoazepine molecules with significant yields. The thiazinoazepines that have been synthesized contain NH functional groups with acidic protons and demonstrate notable antioxidant activity. The (3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide), MTT assay was utilized to evaluate the cytotoxicity of all the synthesized compounds in vitro against cancer cell lines (MCF-7 and A549) as well as normal cell lines). Cytotoxicity refers to the ability of a compound to kill cells. The derivative 6e was shown to be the most potent cytotoxic agent, similar to doxorubicin in its lack of selectivity. Alternatively, compound 6b might be considered as a compound that is equally effective but more selective than doxorubicin. Quantum chemical approaches utilizing density functional theory have been utilized to enhance comprehension of reaction mechanisms. The used technology for synthesizing thiazinoazepines provides several advantages, including rapid reaction kinetics, outstanding product yield, and straightforward product isolation.
A novel multicomponent reaction strategy was employed to achieve high-yield synthesis of new cyclopentapyrrol derivatives. The methodology involved the use of vinilydene Meldrum's acid, ethyl 2-amino-4-dioxo-4-arylbutanoates, alkyl bromides and primary amines. The reaction was carried out at the reaction temperature in an aqueous medium. The antioxidant properties of the newly synthesized compounds are attributed to the presence of the NH functional group, and were confirmed through two standard evaluation methods. The antibacterial activity of the synthesized cyclopentapyrrols was assessed using the disc diffusion technique against two Gram-negative bacterial strains. Additionally, these compounds demonstrated inhibitory effects against Gram-positive bacteria. This synthetic approach offers several advantages, including high product yields, short reaction times, and straightforward product isolation procedures.