Electron-deficient Acetylenic Compounds Research Articles

Investigation of the Biological Activity of Pyrrolo[1,2-a]imidazole Derivatives Produced by a Green One-Pot Multicomponent Synthesis of Ninhydrins

Aims & Objective: This study entailed the creation of a new variation of pyrroloimidazoles with exceptional efficacy through chemical synthesis. The synthesis was accomplished by tricomponent reactions utilizing ninhydrins, diamines, and activated acetylenic compounds in an aqueous setting, leading to significant yields. The antioxidant properties of recently synthesized Pyrroloimidazoles derivatives have been ascribed to the existence of NH and OH groups, which were evaluated using two techniques. The antimicrobial effectiveness of recently developed pyrroloimidazoles was evaluated using a disk diffusion technique against both Gram-negative and Gram-positive bacteria. Materials and Methods: The study team utilized high-quality starting chemicals, solvents, and reagents with consistent chemical and physical properties. The Shimadzu IR-460 spectrometer was used in a KBr medium to get the Ft-IR spectra of the synthesized nanocatalyst. Furthermore, we employed a Bruker DRX-400 AVANCE spectrometer to acquire 1H-NMR and 13C-NMR spectra of the synthesized compounds. The spectrometer utilized in this investigation functions at a frequency of 400 MHz. The solvent employed for the spectra of produced compounds was CDCl3, with TMS serving as the internal standard. The mass spectra of the produced compounds, which have an ionization potential of 70 eV, were obtained using the Finnigan MAT 8430 spectrometer. Elements of produced compounds were subjected to elemental analysis using the Heraeus CHN-O-Rapid analyzer. Results: This work investigated the three-component reaction involving ninhydrins 1, diamines 2, and electron-deficient acetylenic compounds 3 for the eco-friendly production of pyrroloimidazoles derivatives 4 in water-based solutions at normal temperature. The results indicated that these molecules displayed noteworthy efficacy, similar to that of conventional antioxidants. Also, the results indicated that the synthesized pyrroloimidazoles have bacteriostatic properties. Conclusion: In summary, this study aimed to examine the environmentally friendly characteristics of ninhydrins, diamines, and electron-deficient acetylenic compounds when dissolved in water at normal room temperature. The research resulted in the successful production of new pyrroloimidazole derivatives with a high rate of success. This study conducted a more in-depth analysis of the antioxidant properties of the synthesized pyrroloimidazoles 4a-4d by the utilization of two techniques: DPPH radical scavenging and FRAP assays. The results indicated that these molecules displayed noteworthy efficacy, similar to that of conventional antioxidants. Furthermore, we utilized both Gram-positive and Gram-negative bacteria to showcase the antibacterial effectiveness of the synthesized pyrroloimidazoles by the disk diffusion technique. The results indicated that the synthesized pyrroloimidazoles have bacteriostatic properties. These reactions provide benefits, such as efficient utilization of atoms, generation of large quantities of products, and straightforwardness of the reaction.

Green preparation of new pyrimidine triazole derivatives via one-pot multicomponent reactions of guanidine.

In this research the goal was to produce novel pyrimidine triazole compounds in high yields using triethylamin as an efficient catalyst. These new compounds were synthesized by using multicomponent reaction of aldehydes, guanidine, electron deficient acetylenic compounds, tert-butyl isocyanide and hydrazonoyle chloride in aqueous media. Due to the presence of an NH group, which was assessed using two different methodologies, newly synthesized pyrimidine triazoles have antioxidant properties. Additionally, the antibacterial activity of newly created pyrimidine triazoles was assessed using the disk distribution method with two different types of Gram-positive bacteria and Gram-negative bacteria, demonstrating that the use of these compounds prevented the growth of bacteria. Applied to the preparation of pyrimidine triazole derivatives, this method has short reaction times, high product yields, and the ability to separate catalyst and product using simple procedures.

Green Synthesis and Theoretical Study of New Imidazopyrimidine Derivatives via One‐Pot Multicomponent Reactions

AbstractAg/Fe3O4/SiO2@MWCNTs MNCs magnetic nanocomposites as an effective catalyst was employed for generating of imidazopyrimidine derivatives in high yields. The structure of synthesized nanoatalyst was confirmed by SEM, XRD, TEM, VSM, EDX and XPS analysis. These new compounds were synthesized by using multicomponent reaction of cyclic guanidine derivatives, electron deficient acetylenic compounds, tert‐butyl isocyanide, ethyl bromopyruvate and synthesized nanocatalyst in aqueous media at room temperature. It should be mentioned that the high performance of nanocatalyat was synthesized by using water extract of Petasits hybridus leaves, which was utilized in these reactions for many times to confirm the reusability of nanocatalyst. The antioxidant property of new synthesized imidazopyrimidine was evaluated by two procedures and compound 5 b have the high property relative to other compounds. Also, the antimicrobial activity of new generated imidazopyrimidine was evaluated by disk distribution process utilizing two kinds of Gram‐negative bacteria and Gram‐positive bacteria; proving bacterial growth was stopped by using of these compounds. Also, to better understanding reaction mechanism density functional theory (DFT) based quantum chemical methods have been applied. Applied to the preparation of imidazopyrimidine derivatives, this method has short reaction times, high product yields, and the ability to separate catalyst and product using simple procedures.

New MCRs: Preparation of Novel Derivatives of Pyrazoloazepines in Ionic Liquid and Study of Biological Activity

In the present investigation, we have effectively synthesized innovative pyrazoloazepine derivatives with notable yields. The synthesis was successfully accomplished by means of a multicomponent reaction that was carried out in an ionic liquid at ambient temperature conditions. The constituents implicated in this procedure consisted of NH-acids such as isatins, α-halo ketones, electron deficient acetylenic compounds, hydrazine, and hydrazonoyl chlorides. Significantly, the inclusion of an NH group appeared as a crucial characteristic in the resultant compounds. Our investigation encompassed the examination of the antioxidant capabilities exhibited by these substances. The study utilized various assays, including ferric reduction capacity and diphenyl-picrylhydrazine (DPPH) radical trapping, to investigate the possible antioxidant benefits of the substances. The antioxidative capacity of the produced pyrazoloazepine compounds was evaluated by various evaluations. The synthetic approach we employ offers numerous advantages. To begin with, the prompt response time enables the expedited generation of complex compounds. Furthermore, the significant outputs of the specific items highlight the effectiveness of our approach. The ease with which the catalyst and products can be separated enhances the efficiency of the purification procedure.

Green Synthesis and Biological Study of New Imidazothiazines Using New MCRs: A Combined Experimental and Theoretical Investigation

For the performing this research multicomponent reaction of isatin, electron-deficient acetylenic compounds, α-haloketones, ammonium acetate, isothiocyanates and methyl aziridine in aqueous at room temperature was investigated for the production of novel derivatives of azepinothiazine in excellent yields. The synthesized azepinothiazines have OH, NH2 and NH functional groups that have acidic hydrogen and show high antioxidant activity. These synthesized compounds also displayed antimicrobial activity by using the disk diffusion procedure and two Gram-positive and Gram-negative bacteria. Also, to better understanding reaction mechanism density functional theory-based quantum chemical methods have been applied. The employed process for the production of azepinothiazine has some benefits such as short time of reactions, excellent efficiency of the product, easy separation of products.

Green Synthesis and Biological Activity Investigation of New Pyrimidotriazinoazepines

In this research, one-pot multicomponent reactions of isatins, electron deficient acetylenic compounds, α-haloketones, ammonium acetate, isocyanates and hydrazonoyl chlorides in aqueous media at room temperature was investigated for the production of novel derivatives of pyrimidotriazinoazepine in excellent yields. The synthesized pyrimidotriazinoazepines have OH and NH functional groups that have acidic hydrogen and show high antioxidant activity. These synthesized compounds also displayed antimicrobial activity by using the disk diffusion procedure and two Gram-positive and Gram-negative bacteria. The employed process for production of pyrimidotriazinoazepines has some benefits such as short time of reactions, excellent efficiency of product and easy separation of products. Highlights In medicinal chemistry, the heterocyclic compounds have a well-known subject due to having wide area of biological activities of these compounds. Therefore these compounds are very important and for the synthesis of these compounds existed many procedures. Multicomponent reactions (MCRs) is one of the process for the preparation of biological activities heterocyclic compounds with many benefits such as having atom economic, an useful and excellent efficiency in the generation of heterocyclic compounds relative to many stage reactions for preparation of organic compounds The present procedure avoids the use of toxic solvent. Azepines, which have a seven-membered aza-heterocyclic fused aromatic ring, are of interest because of their biological activity and use as building blocks for natural product synthesis and drug discovery.

An Efficient Synthesis and Study of Biological Activity of New Pyrimidoazepines Using Ag/Fe3O4/TiO2/CuO@MWCNTs Magnetic Nanocomposites: A Combined Experimental and Theoretical Investigation

In this research, we studied the one-pot multicomponent reaction of isatoic anhydride, electron deficient acetylenic compounds, α-haloketones, ammonium acetate, carbodiimides and Ag/Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites as catalyst in aqueous at room temperature for the production of novel derivatives of pyrimidoazepines in excellent yields. Moreover, reduction of organic pollutants such 4-nitrophenol (4-NP) was performed by synthesized Ag/Fe3O4/TiO2/CuO@MWCNTs in water at room temperature. The outcomes showed this catalyst was decreased organic pollutants in few seconds. The synthesized pyrimidoazepines have OH and NH functional groups that have acidic hydrogen and show high antioxidant activity. These synthesized compounds also displayed antimicrobial activity by using the disk diffusion procedure and two Gram-positive and Gram-negative bacteria. Also, to better understand the reaction mechanism density functional theory (DFT) based quantum chemical methods have been applied. The employed process for the production of pyrimidoazepines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products.

Synthesis and Biological Activity Investigation of New Oxazolopyrimidoazepine Derivatives: Application of Ag/Fe3O4/TiO2/CuO@MWCNTs MNCs in the Reduction of Organic Pollutants

Ag/Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites were synthesized by the Petasites hybridus rhizome water extract as green media and used for one-pot multicomponent reaction of isatins, electron deficient acetylenic compounds, α-haloketones, ammonium acetate, tert-butyl isocyanide and ethyl bromopyruvate in aqueous media at room temperature for the production of novel derivatives of oxazolopyrimidoazepines in excellent yields. The synthesized oxazolopyrimidoazepines have OH and NH functional groups that have acidic hydrogen and show high antioxidant activity. Moreover, reduction of organic pollutants such 4-nitrophenol (4-NP) was performed by synthesized Ag/Fe3O4/TiO2/CuO@MWCNTs in water at room temperature. The outcomes showed this catalyst was decreased organic pollutants in few seconds. The employed process for the production of oxazolopyrimidoazepines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products. HIGHLIGHTS Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication and applications of chemical products. Among solvents, water is a green solvents and very suitable for performing organic reaction. The present procedure avoids the use of toxic solvent. Some representatives of this class of azaheterocycles are known as antiviral agents, glycosidase inhibitors, anticancer agents or antidiabetics. Therefore, in view of their medicinal relevance, an increasing number of synthetic methods have been described in recent years for the construction of highly substituted azepine derivatives.

Green Synthesis and Antioxidant Activity Investigation of New Thiazinotriazines: Reduction of Organic Pollutant Using Fe3O4/TiO2/CuO@MWCNTs MNCs

The Petasites hybridus rhizome water extract was used as a green media for the preparation of the Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites (Fe3O4/TiO2/CuO@Multi-Walled Carbon Nanotubes) and its activity was evaluated by using it in the one-pot multicomponent reaction of isatoic anhydrides, electron deficient acetylenic compounds, α-haloketones, ammonium acetate, isothiocyanates and hydrazoyl chloride in aqueous media at room temperature for the production of novel derivatives of thiazinotriazines in excellent yields. Moreover, reduction of organic pollutants such 4-nitrophenol (4-NP) was performed by synthesized Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites in water at room temperature. The outcomes showed this catalyst decreased organic pollutants in few seconds. The synthesized thiazinotriazines have OH and NH functional groups that have acidic hydrogen and show high antioxidant activity. The employed process for the production of thiazinotriazines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products. HIGHLIGHTS In medicinal chemistry, the heterocyclic compounds have a well-known subject due to having wide area of biological activities of these compounds. Therefore these compounds are very important and for the synthesis of these compounds existed many procedures. Multicomponent reactions (MCRs) is one of the process for the preparation of biological activities heterocyclic compounds with many benefits such as having atom economic, an useful and excellent efficiency in the generation of heterocyclic compounds relative to many stage reactions for preparation of organic compounds The present procedure avoids the use of toxic solvent. Benzazepines, which have a seven-membered aza-heterocyclic fused aromatic ring, are of interest because of their biological activity and use as building blocks for natural product synthesis and drug discovery.

Green Synthesis and Biological Activity Investigation of New Thiazinotriazines: A Combined Experimental and Theoretical Investigation

The Petasites hybridus rhizome water extract was used as a green media for the preparation of the Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites and its activity was evaluated by using it in the one-pot multicomponent reaction of isatoic anhydrides, electron deficient acetylenic compounds, α-haloketones, ammonium acetate, isothiocyanates and hydrazonoyl chloride in aqueous media at room temperature for the production of novel derivatives of thiazinotriazines in excellent yields. The synthesized thiazinotriazines have OH and NH functional groups that have acidic hydrogen and show high antioxidant activity. Moreover, reduction of organic pollutants such 4-nitrophenol (4-NP) was performed by synthesized Fe3O4/TiO2/CuO@MWCNTs in water at room temperature. The outcomes showed this nanocatalyst was decreased organic pollutants in few seconds. Also, to better understanding reaction mechanism density functional theory based quantum chemical methods have been applied. The employed process for production of thiazinotriazines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products.

Production of Pyrimidobenzazepine Derivatives and Reduction of Organic Pollutant Using Ag/Fe3O4/TiO2/CuO@MWCNTs MNCs

The Petasites hybridus rhizome water extract as green media was used for the preparation of the Ag/Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites and its activity was evaluated by using in the one-pot multicomponent reaction of isoquinoline, α-haloketones, 2-amino benzoic acids, diethyl carbonate, electron deficient acetylenic compounds, ammonium acetate, and tert-butyl isocyanide in water at room temperature for the production of novel derivatives of pyrimidobenzazepines in excellent yields. Moreover, reduction of organic pollutants such 4-nitrophenol was performed by synthesized Ag/Fe3O4/TiO2/CuO@MWCNTs in water at room temperature. The outcomes showed this catalyst was decreased organic pollutants in few seconds. Because of having azepine moiety, the synthesized compounds show good antioxidant activity. These synthesized compounds also displayed antimicrobial activity by using the disk diffusion procedure and two Gram-positive and Gram-negative bacteria. The employed process for production of benzazepines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products.

Fe3O4/CuO Nanocomposite Promoted Green Synthesis of Functionalized Quinazolines Using Water Extract of Lettuce Leaves as Green Media: Study of Antioxidant Activity

In this work, five component reactions are utilized for the production of quinazoline derivatives by utilizing the one-pot reaction of 3-hydroxyphthalaldehyde, ethylenediamine, alkyl bromides, electron deficient acetylenic compounds and ethyl bromoacetate in vicinity of Fe3O4/CuO nanocomposites as a high performance catalyst at environment temperature in water extract of lettuce leaves as green solvent. Also, water extract of lettuce leaves was used for synthesis of Fe3O4/CuO nanocomposites. The existing quinazoline core in the synthesized compounds caused to ability of antioxidation of synthesized quinazoline. For confirmation of this point, we are used DPPH radical trapping and ferric ion reducing power tests. Outcomes of these tests show that synthesized quinazolines have low DPPH radical trapping and good reducing ability of ferric ion. The excellent yield of reaction, green media and easy separation of product and catalyst are some benefits of this procedure. Highlights Water extract of Lettuce leaves was used as solvent for the preparation of quinazolines as cyclic heteroaromatic systems. The present procedure avoids the use of toxic solvent. The present procedure runs in water extract of Lettuce leaves as a green media. This recoverable catalyst makes this protocol attractive and useful as an industrially viable and eco-safe solvent with high yields of products.

ZnO/Fe3O4 nanoparticles promoted green synthesis of pyrazolo pyrimidinones: Study of antioxidant activity

AbstractThe preparation of pyrazolo pyrimidinone derivatives was performed by using five component reactions of phthalaldehyde, cyanomethylamine, electron deficient acetylenic compounds, isocyanate, hydrazine, and catalytic amounts of ZnO/Fe3O4‐magnetic nanoparticles as a high performance catalyst under ultrasonic conditions at ambient temperature in aquause media at room temperature. It should be mentioned that this catalyst was prepared using Spinacia oleracea water extract. In addition, for investigation of antioxidant ability, radical trapping by DPPH and reducing power of ferric ion experiments was performed. As a result, synthesized compounds show excellent radical trapping by DPPH and good reducing ability of ferric ion. The current procedure has the benefits for instance excellent yield of reaction, green media, and easy separation of product and catalyst.

Green synthesis and investigation of antioxidant ability new pyrazines containing pyrrolo[2,1‐a]isoquinolines derivatives

AbstractIn this study, a new, easy and high yield procedure is investigated for the generation of pyrazine containing pyrrolo[2,1‐a]isoquinoline derivatives using multicomponent reaction of phthalaldehyde or its derivatives, primary amines, α‐haloalketones, electron deficient acetylenic compounds, ammonium acetate and KF/Clinoptilolite nanoparticles (KF/CP NPs) as catalyst in water at room temperature. The reactions of 2‐hydroxy phthalaldehyde, primary amines, α‐haloketones, electron deficient acetylenic compounds, and ammonium acetate in the presence of KF/CP NPs as catalyst in water at room temperature produce pyrazine derivatives in good yields. Also, in this work, antioxidant ability was studied for a number of prepared compounds employing the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical scavenging and power of compounds for reducing of ferric ion experiments and evaluating results with synthetic antioxidants (TBHQ and BHT). Comfortable, simple, fast and fresh procedure is the advantages of this study.

Green synthesis of indol-2-one derivatives from N-alkylisatins in the presence of KF/clinoptilolite nanoparticles

KF/clinoptilolite nanoparticles were used as an effective heterogeneous catalyst for the synthesis of spiro[indole-3,2'-pyran] derivatives via three-component reactions of N -alkylisatins, 1,3-dicarbonyl compounds, and electron-deficient acetylenic compounds under solventfree conditions at 80°C. The present protocol has significant advantages, such as high yields, easy purification, and low environmental impact.

Four-Component Reaction of Trialkyl Phosphites, Amines, and Electron-Deficient Acetylenic Compounds: Synthesis of Phosphonate Derivatives in Water

An effective route for the synthesis of phosphonate derivatives is described. This procedure involves the reaction of a trialkyl phosphites and dialkyl acetylenedicarboxylate in the presence of amines in water as the solvent at room temperature.

ChemInform Abstract: Synthesis of 4‐Oxo‐2,5‐cyclopentadiene Using Multi‐Component Reactions of Primary Amines and Electron Deficient Acetylenic Compounds with Triphenylphosphine in Water.

Abstract7 Cyclopentadiene derivatives of type (IV) are prepared using a multicomponent reaction of primary amines and electron‐deficient acetylenic compounds with triphenylphosphine in water.

Synthesis of 4-oxo-2,5-cyclopentadiene Using Multi-component Reactions of Primary Amines and Electron Deficient Acetylenic Compounds with Triphenylphosphine in Water

7 Cyclopentadiene derivatives of type (IV) are prepared using a multicomponent reaction of primary amines and electron-deficient acetylenic compounds with triphenylphosphine in water.

ChemInform Abstract: One‐Pot Synthesis of N‐Alkyl Sulfonyl Hydrazones by Dialkyl Acetylenedicarboxylate‐Mediated Reaction of Trialkylphosphites with Sulfonyl Hydrazones.

Abstract Stable derivatives of N-alkyl sulfonyl hydrazone were obtained in excellent yields from the reaction between electron-deficient acetylenic ester compounds and sulfonyl hydrazones in the presence of trialkylphosphites in dichloromethan at room temperature. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

One-Pot Synthesis of N-Alkyl Sulfonyl Hydrazones by Dialkyl Acetylenedicarboxylate-Mediated Reaction of Trialkylphosphites with Sulfonyl Hydrazones

Stable derivatives of N-alkyl sulfonyl hydrazone were obtained in excellent yields from the reaction between electron-deficient acetylenic ester compounds and sulfonyl hydrazones in the presence of trialkylphosphites in dichloromethan at room temperature. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]