Malononitrile In Ethanol Research Articles

A novel Cu(II) nanoparticles anchored on cyanuric chloride-attached magnetic nanocatalyst: A highly stable, recyclable and efficient nanocatalyst for the synthesis of chromene derivatives

As a novel core-shell magnetic nanocatalyst, a copper nanocatalyst, Cu(II)-Schiff base-TCT-APTES@SiO2@Fe3O4 was successfully synthesized through the reaction of the cyanuric chloride grafted onto the core-shell magnetic nanocatalyst with Schiff base complex and finally treated with Cu(NO3)2·3H2O. The noteworthy point is that the novel Schiff base separated by employing hydrazine with 2-pyridinecarboxaldehyde was synthesized and purified by a simple washing and identified by FT-IR, 1H NMR and 13C NMR spectrums. The catalyst was studied relying on various techniques and spectroscopic procedures including FT-IR, SEM, TEM, XPS, XRD, VSM, BET, TGA, and ICP analyses. The TEM images indicated that the catalyst was synthesized with an average size of 37–47 nm and a spherical shape. BET analysis showed that our catalyst has been synthesized with mesoporous structure and high surface area (52.55 m2/g). Moreover, the XPS results clearly demonstrated the peak at 937.2 eV and 949.2 eV that was related to the presence of Cu(II) in structure of catalyst. Then, copper nanocatalyst was successfully tested for the one-pot three component reaction of chromene derivatives of various aldehydes, phenols (2-hydroxynaphthalene-1,4-dione, resorcinol and β-naphthol) and malononitrile in ethanol under reflux conditions. All products were obtained in excellent yields for a diverse range of aromatic aldehydes. TON and TOF numbers for the compound 4j with the highest yield were found to be 192 and 581.8 h−1, respectively. Further, the copper catalyst can be reused by external magnetic field over seven times with a negligible loss in activity, showing 0.08% leaching of Cu after 7 times recycling. Also, Density Functional Theory (DFT) calculations were carried out to investigate the electrostatic potential (ESP), natural bond orbital (NBO), images of HOMO and LUMO orbitals and drawing the reaction mechanism using total energy of reactant and product.

DIPEA‐Assisted Efficient One‐Pot Three‐Component Synthesis of Novel β‐Carboline Tethered Pyran Derivatives

AbstractA potential DIPEA‐assisted approach has been unfolded for the synthesis of novel β‐carboline tethered‐4H‐pyran derivatives via one‐pot condensation of 1‐formyl‐9H‐β‐carbolines, β‐keto esters and malononitrile in ethanol at ambient temperature. A library of 28 new β‐carboline tethered 4H‐pyran derivatives has been developed. The significant features of the present strategy include high efficiency, excellent yield, inexpensive catalyst, mild reaction conditions, multicomponent character of reaction and simple purification procedure.

The Green and Efficient One-pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives

Glutamic acid is used as an efficient organocatalyst for one-pot synthesis of tetrahydrobenzo [b]pyran via condensation of an aromatic aldehyde, dimedone and malononitrile in ethanol: water (1:4) as solvent at reflux temperature. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive.

Synthesis of Bis‐Nicotinonitrile Derivatives and Investigations of Antimicrobial and Antibiofilm Activities

AbstractIn this study aimed to the synthesis of novel bis‐nicotinonitrile derivatives starting from 1,3‐bis‐chalcones and investigate their antimicrobial activity potentials. Bis‐nicotinonitrile derivatives were synthesized from 1,3‐bis‐chalcone derivatives reacted with malononitrile in ethanol in the presence of potassium carbonate. Characterization of the obtained compounds was carried out by spectroscopic methods. In total, 12 new 1,3‐phenylene‐bis‐nicotinonitrile derivatives were synthesized. Finally, the antimicrobial and antibiofilm activities of synthesized 1,3‐phenylene‐bis‐nicotinonitrile derivatives were tested against 5 microorganisms. As a result, it was observed that the synthesized new nicotinonitrile derivatives were quite active especially in terms of antibiofilm activity.

Bimetallic CoCeO2 oxide nanoparticles: An efficient and reusable heterogeneous catalyst for the preparation of 2‐amino‐3‐cyano‐4H‐pyran derivatives

AbstractCoCeO2 NPs were successfully synthesized and confirmed using x‐ray diffraction (XRD), field emission scanning electron microscopy (FESEM), and high‐resolution transmission electron microscopy (HRTEM) techniques. The catalytic performance of the synthesized CoCeO2 NPs catalyst was examined during the one‐pot multicomponent synthesis of biologically significant 2‐amino‐3‐cyano‐4H‐pyran derivatives. The reaction was easily accomplished using a one‐pot, three‐component reaction of dimedone, aryl aldehydes, and malononitrile in ethanol under reflux, with excellent yields and a short reaction time. The current catalytic system is more appealing because of its simple reaction conditions, uncomplicated product isolation, economic feasibility, and reusability of the catalyst free from significant loss of activity. This process offers an effective strategy for the synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives.

Synthesis, Characterization and Catalytic Potency of Zn-based MOF for Knoevenagel Condensation Reaction

Abstract: A Zn based metal organic framework with pyridine 2, 5-dicarboxylate (Zn-based MOF) were prepared as a reusable heterogeneous catalyst using solvothermal method. Zn-based MOF was used as heterogeneous catalyst for synthesis 5-arylidene malononitrile in ethanol under reflux condition. The attractive features of present method are mild reaction condition, short reaction time, simplicity, easy separation of catalyst and excellent yield. Keywords: Metal organic framework, heterogeneous catalyst, solvothermal method.

A sustainable molybdenum oxide loaded on zirconia (MoO3/ZrO2) catalysed multicomponent reaction to synthesise novel dihydropyridines

We have synthesised the robust molybdenum oxide supported on zirconium oxide (MoO3/ZrO2) by a simple wet-impregnation method. It proved an effective catalyst for synthesising eleven novel dihydropyridine derivatives in excellent yields (92–96%). The one-pot four-component fusion involved dimethyl-2-amine pyridine, diethyl but-2-ynedioate, various benzaldehydes and malononitrile in ethanol. The swift reactions at room temperature were accomplished in <18 min. The nanocomposite catalyst is stable up to five successive runs with similar catalytic activity. Swift reaction, recyclability, excellent yields, mild conditions, simple workup and column-free protocol are the advantages of this method.

Design of a Schiff Base Complex of Copper Coated on Epoxy-Modified Core-Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various Chromene-Annulated Heterocycles.

An ecofriendly inorganic–organic hybrid and novel Schiff base complex of copper coated on epoxy-modified Fe3O4@SiO2 MNPs was successfully designed and prepared from readily available chemicals. In this method, a Schiff base complex as a linker is utilized to protect copper nanoparticles to the core–shell Fe3O4 exterior without agglomeration. The resulted Schiff base complex of copper coated on epoxy-modified Fe3O4@SiO2 MNPs was characterized and confirmed via different analyses such as FT-IR, TGA, XRD, VSM, FE-SEM, TEM, ICP, EDX, and BET. The novel catalyst was examined for the synthesis of various chromene-annulated heterocycles through the one-pot three component reaction of aromatic aldehydes, various phenols (2-hydroxynaphthalene-1,4-dione/resorcinol/β-naphthol), and malononitrile in ethanol at reflux conditions. This method includes important aspects like no usage of column chromatography, very short reaction times, simplicity of product isolation using ethanol, excellent yields, simple procedures, and magnetic recoverability of the catalyst. All in all, our method makes a novel and significant advancement in the synthesis of various chromene-annulated heterocycles.

Expedient Synthesis and Antibacterial Activity of Tetrahydro-1′H-spiro[indoline-3,4′-quinoline]-3′-carbonitrile Derivatives Using Piperidine as Catalyst

AbstractA convenient synthesis of 2′-amino-7′,7′-dimethyl-2,5′-dioxo-1′-(phenylamino)-5′,6′,7′,8′-tetrahydro-1′H-spiro[indoline-3,4′-quinoline]-3′-carbonitrile derivatives has been designed using different substituted isatins, various 5,5-dimethyl-3-(2-phenylhydrazinyl)cyclohex-2-enones (arylhydrazones of dimedone) and malononitrile in ethanol with piperidine as catalyst at room temperature. The structures of the synthesized compounds have been elucidated by various spectroscopic techniques. The selected compounds have also been evaluated for their antibacterial activities against human pathogenic bacteria.

Investigation of the reactivity of (1H-benzo[d]imidazol-2-yl)acetonitrile and (benzo[d]thiazol-2-yl)acetonitrile as precursors for novel bis(benzo[4,5]imidazo[1,2-a]pyridines) and bis(benzo[4,5]thiazolo[3,2-a]pyridines)

A synthesis of novel bis(benzo[4,5]imidazo[1,2-a]pyridines) via the reaction of the appropriate bis(aldehyde) with 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and malononitrile in ethanol at reflux in the presence of piperidine was reported. On the other hand, attempted synthesis of bis(benzo[4,5]thiazolo[3,2-a]pyridines) by a three-component reaction of the appropriate bis-aldehyde with malononitrile and (benzo[d]thiazol-2-yl)acetonitrile under similar reaction conditions was unsuccessful. The reactions gave instead the corresponding novel bis(benzo[d]thiazol-2-yl)acrylonitriles.

Green synthesis of Fe3O4/ZnO magnetic core‐shell nanoparticles by Petasites hybridus rhizome water extract and their application for the synthesis of pyran derivatives: Investigation of antioxidant and antimicrobial activity

In this research, Fe3O4/ZnO magnetic core‐shell nanoparticles (Fe3O4/ZnO MCNPs) were synthesized through a green method using Petasites hybridus rhizome water extract as a reducing and stabilizing agent. The morphology and size of the Fe3O4/ZnO MCNPs was identified by X‐ray diffraction, scanning electron microscopy, and Energy‐dispersive X‐ray spectroscopy (EDX) analysis. The catalytic activity of the Fe3O4/ZnO MCNPs was evaluated in the efficient and green preparation of pyran derivatives in excellent yield using three‐component reactions of dimedone, aldehydes, and malononitrile in ethanol at room temperature. The ability of some synthesized compounds to scavenge the 2,2‐diphenyl‐1‐picrylhydrazyl radical was measured and the results proved this observation. Moreover, the antimicrobial activity of some synthesized compounds was proved by employing the disk diffusion test on Gram‐positive and Gram‐negative bacteria. The results for the disk diffusion test showed that compounds (4c, 4d, 4f and 4g) prevented bacterial growth.

Efficient Synthesis of Pyridin‐2(1H)‐ones From a Series of Readily Available Enaminones Under Mild Conditions

A facile and efficient synthesis of substituted pyridin-2(1H)-ones has been developed by the reaction of readily available enaminones with malononitrile in ethanol at room temperature in yields of 85–95%. This protocol, which combines construction and modification of the pyridin-2(1H)-ones ring under Vilsmeier conditions (dimethylformamide/POCl3), increases the structural diversity of the final products from readily available materials.

Facile Synthesis of New 6‐Alkylamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile Derivatives

Some new derivatives of 6‐alkylamino‐1,3‐diphenyl‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile have been prepared through a Knoevenagel condensation reaction of 5‐chloro‐1,3‐diphenyl‐1H‐pyrazole‐4‐carbaldehyde with malononitrile in ethanol containing a few drops of glacial acetic acid at reflux temperature followed by cyclization with primary alkyl amines in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene as catalyst in refluxing ethanol. The products were characterized on the basis of IR, 1H NMR, and 13C NMR spectral and microanalytical data. The 1H NMR data ruled out the formation of the alternative cyclized isomers 6‐imino‐7‐alkyl‐1,3‐diphenyl‐6,7‐dihydro‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitriles.

Synthesis of new indole derivatives using one- pot multicomponent reaction with antiproliferative towards normal and cancer cell lines

Background and objectives Indoles derivatives are natural products, which are well known for their anticancer activity due to its ability to induce cell death for many cancer cell lines. The aim of this study is to synthesize some new heterocyclic compounds derived from 1H-indole-3-carbaldehyde, malononitrile, and different reagents namely: active methylene derivatives, amine derivatives, and resorcinol. The newly synthesized derivatives were prepared and confirmed by their IR, Mass, and 1NMR spectra; and were also tested for their antiproliferative potency towards human breast cancer (MCF-7) and normal murine fibroblast (BALB/3T3) cell lines. Materials and methods The synthesis of new indole derivatives (3a-e) was achieved by the three-component reactions of 1H-indole-3-carbaldehyde (1), ethyl 3-oxobutanoate, 5,5-dimethyl cyclohexane-1,3-dione (Dimidone), barbituric, thiobarbituric acid, and cyclohexanone (2a-e), respectively; and malononitrile in the presence of triethylamine. Compound (4) was afforded by fusing of compound (3a) with thiourea. Also, compounds (5a, b) were yielded by the grinding of compounds (3c, d) with formic acid. On the other side, one-pot synthesis of 7a-d has been achieved via three-component of 1H-indole-3-carbaldehyde (1), and malononitrile in the presence of amine derivatives (namely, 2,4-dinitroaniline, 3-nitroaniline, 3-bromoaniline, and 4-methoxyaniline) (6a-d), respectively, by condensation. Also, compounds (8, 9) were obtained by refluxing of compounds (7a, b) with formic acid. Compound (10) was afforded by condensing the mixture of 1H-indole-3-carbaldehyde (1) with resorcinol in the presence of malononitrile and triethylamine. The newly synthesized derivatives were tested for their antiproliferative potency towards human breast cancer (MCF-7) and normal murine fibroblast (BALB/3T3) cell lines. Results indicated that they showed significant in-vitro antiproliferative activity. Results and conclusion A novel protocol for the preparation of indole derivatives (3a-e) using the three-component reactions of 1H-indole-3-carbaldehyde (1) with active methylene compounds namely: ethyl 3-oxobutanoate, 5, 5-dimethy cyclohexane-1, 3-dione (Dimidone), barbituric acid, thiobarbituric acid, and cyclohexanone (2a-e); and malononitrile in ethanol and triethylamine as catalyst were proceeded in one step. Also, compounds (3a, 3c, d) were reacted with thiourea/and formic acid, respectively, to give compounds (4 and 5a, b). The 3-indole derivatives (7a-d) were formed via condensation of the amine derivatives (6a-d) with indole aldehydes (1) and malononitrile. Compounds (8 and 9) were afforded by condensation of compounds (7b, c) with formic acid, 2-amino-chromene (10) was produced by reaction of resorcinol, 1H-indole-3-carbaldehyde (1), and malononitrile. The in-vitro study showed that most of the prepared compounds gave similar activity towards breast cancer cell line MCF-7 but did not reveal the cytotoxic potency against normal cell line. This means that most of these compounds kill cancer cells but have no or slight effects on normal cells. The newly synthesized derivatives were tested for their antiproliferative potency towards human breast cancer (MCF-7) and normal murine fibroblast (BALB/3T3) cell lines. The results showed that the in-vitro antiproliferative activity of the prepared compounds was significant and could thus be investigated for further in vivo and pharmacokinetic studies.

Cu(II)-β-cyclodextrin-catalyzed synthesis of spiro[indoline-3,4′-pyrano[3,2-c]chromene]-3′-carbonitrile derivatives

ABSTRACTCu(II)-β-cyclodextrin-catalyzed synthesis of spiro[indoline-3,4′-pyrano[3,2-c]chromene]-3′-carbonitriles through the reaction of isatin derivatives, 4-hydroxycoumarin, and malononitrile in ethanol at room temperature.

Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile

The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2′-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2″,3″:2′,3′]pyrrolo[3′,4′:4,5]pyrrolo[2,1-a]isoquinoline derivatives. However, the three-component reaction of N-cyanomethylisoquinolinium chloride, isatins and ethyl cyanoacetate mainly resulted in functionalized spiro[indoline-3,8′-pyrido[2′,3′:4,5]pyrrolo[2,1-a]isoquinolines].

ChemInform Abstract: Ceria‐Vanadia/Silica‐Catalyzed Cascade for C—C and C—O Bond Activation: Green One‐Pot Synthesis of 2‐Amino‐3‐cyano‐4H‐pyrans.

AbstractA three‐component cyclocondensation of dimedone, aromatic aldehydes, and malononitrile in ethanol provides a green and efficient synthesis of the title compounds.

V-CaHAp as a recyclable catalyst for the green multicomponent synthesis of benzochromenes

A simple and efficient one-pot method has been developed for the synthesis of benzochromenes (4a–k) using V-CaHAp as a heterogeneous catalyst by the condensation of aldehydes, β-naphthol and malononitrile in ethanol as solvent at room temperature for 20min. The reaction, with this catalyst was carried out under mild reaction conditions with very good to excellent yields (89–98%). The material can be recycled very easily and reused for at least 6 runs without substantial loss in activity, which makes this methodology environmentally benign. We achieved a feasible and cost-effective synthesis by using non-toxic materials and minimal catalyst which is easy to handle.

Molecular diversity of the cyclization reaction of 3-methyleneoxindoles with 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitriles

The cyclization reaction of 3-methyleneoxindoles with 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile in ethanol in the presence of DBU at room temperature afforded functionalized 3′-iminospiro[indoline-3,2′-phenanthrenes] in good yields.

Electrocatalytic multicomponent assembling of aminouracils, aldehydes and malononitrile: An efficient approach to 7-amino-pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives

Electrocatalytic multicomponent transformation of 6-aminouracils, aromatic aldehydes and malononitrile in ethanol in an undivided cell in the presence of potassium bromide as an electrolyte leads to 7-amino-pyrido[2,3- d]pyrimidine-6-carbonitrile derivatives in short reaction times (8-20 min) and good to high yields (70-86%).