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Selective reduction–oxidation of dimethyl 3,4-dimethoxythiophene-2,5-dicarboxylate gave methyl 5-formyl-3,4-dimethoxythiophene-2-carboxylate and then methyl 5-[di(1H-pyrrol-2-yl)methyl]-3,4-dimethoxy-thiophene-2-carboxylate, and the latter was used to obtain the corresponding BODIPY derivative. [ABSTRACT FROM AUTHOR]

A one-pot multicomponent method employing substituted indole, ethyl cyanoacetate and aromatic aldehyde was found as an effective catalytic procedure for the synthesis of a novel indole derivatives. The potential of CuO nanoparticles as nanocatalysts for the Knoevenagel condensation and the synthesis of new indole derivatives was investigated. X-Ray diffraction was used to measure the size of the CuO nanoparticles. CuO nanoparticles can be recycled and used again after the reaction course. The ADMET analysis and drug-likeness results indicated that indole derivatives satisfied Lipinski's principles and drug-likeness requirements. The reactivity indices and potential areas obtained from the FMO experiments were successfully used to a range of molecular systems because they yield valuable information. Here, we determined the oxobutanoate derivative's critical areas and likely reactivity directions. The resultant indole derivatives were subjected to various analytical techniques, including mass spectroscopy, 1H and 13C NMR spectroscopy, FT-IR and mass spectrometry. [ABSTRACT FROM AUTHOR]

Pyrazole compounds have garnered attention due to their potential biological and medicinal qualities. Therefore, the purpose of the research being described is to utilize 3,5‐dimethyl‐1H‐pyrazole‐1‐carbothiohydrazide (1) as a starting material in a one‐pot synthesis to create novel pyrazole derivatives with potential biological applications. When either ethanol or acetic acid was added, components 1 and 1,3‐diphenylpropane‐1,3‐dione (2) reacted to produce derivative 3. Compound 1, when combined with ethanol, chemical 2, or acetyl acetone 5 and triethylamine, yielded chemicals 4 and 6 respectively. When ingredient 1 was mixed with ethyl cyanoacetate (7), stearic acid (10), or carboxylic acids 12 a–c, 9, 11, and 13 a–c were formed as a result. The equivalent 1,3,4‐thiadiazine derivatives, 15 and 17, were produced when 1 was mixed with either 14 or 16. The developed compounds′ cytotoxic properties were evaluated against lung and liver cancer. Our research identified a number of interesting bioactive chemicals, among which chemical 17 exhibited the greatest effectiveness against lung and liver cancer as well as the highest selectivity index measurements. It indicated a strong IC50 value of 5.35 and 8.74 μM, accordingly, when compared with 3.78 and 6.39 μM for the reference medication cisplatin. Additionally, its safety for use has been confirmed. [ABSTRACT FROM AUTHOR]

Three-component reaction between sodium azide, ethyl cyanoacetate or malonitrile and arylglyoxals afforded 4,5-disubstituted 1,2,3-triazole derivatives in high yields. All reactions were conducted in ethanol as an environmentally benign solvent at room temperature without using any catalyst or modifier. Stable solid products were easily isolated and purified by washing with water and diethyl ether. The structures of the compounds were proved by 1H and 13C NMR and IR spectral and elemental analysis data. [ABSTRACT FROM AUTHOR]

The condensation of ethyl cyanoacetate and salicylaldehyde would afford either coumarin-3-carboxylate ester or 3-cyancoumarin as the final product. Herein, comparative experiments and density functional theory (DFT) calculations were investigated to pursue a deeper understanding of the critical factor in this reaction. Experimental results indicated that condensation is accomplished through a cascade process, including the Knoevenagel procedure followed by selective cyclization of the phenolic hydroxyl group to the cyano or ester carbonyl group within the intermediate. Product distribution correlates well with the acid–base properties of the catalyst and the ability of the catalyst for forming complex by hydrogen bonds. Also, an efficient and facile approach was developed for the preparation of coumarin-3-carboxylate ester as a major product from the reaction of ethyl cyanoacetate with salicylaldehyde. Low-transition-temperature mixture (LTTM) formed from L-proline and oxalic acid was proved as an inexpensive, easily available, and efficient promoter which not only affords the products in high yields but also avoids the use of hazardous solvent and tedious isolation procedures. [ABSTRACT FROM AUTHOR]

A new method has been developed for the synthesis of 5,5-disubstituted N-methyl-1,3-oxazinanes as a mixture of diastereomers at the 5-position containing monoterpene and branched alkyl substituents in the 5-position. 1,3-Oxazinanes were obtained for the first time by reacting 2,2-substituted 3-aminopropan-1-ols with formaldehyde and sodium borohydride in one stage. [ABSTRACT FROM AUTHOR]

Quinolines are very important compounds due to their numerous biological and pharmacological applications. This article describes the synthesis of new tricyclic quinoline derivatives via intramolecular cyclization of malonic benzylidene derivatives. The malonic benzylidene derivatives 2a-c have been obtained by condensation of N-substituted aldehydes 1a-c with malononitrile or ethyl cyanoacetate. These latter have been cyclized by reflux in DMF to give the compounds 3a-f. The structures of the compounds have been determined by 1 H and 13C NMR spectroscopy, and High-Resolution Mass Spectrometry (HRMS) analysis. Two of the synthesized compounds have been identified and confirmed by X-ray crystallography. [ABSTRACT FROM AUTHOR]

In this research, we synthesized new pyrimidine fused quinoline derivatives in high yields using multicomponent reaction of the 2-amino-4-hydroxyacetophenone, isopropenylacetylene, aldehydes, malononitrile or ethyl cyanoacetate, acetaldehyde and dimethylacetylene dicarboxylate in the presence of catalytic amounts of Fe3O4/KF/Clinoptilolite@MWCNTs magnetic nanocomposites using ionic liquid as green solvent at room temperature. Also, the catalytic activity of the green synthesized Fe3O4/KF/Clinoptilolite@MWCNTs MNCs 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 NCs have very high and effective catalytic activity for organic pollutants within few seconds. The synthesized compounds have NH group in their structure and for this reason have good antioxidant activity. Also, employing Gram-positive and Gram-negative bacteria in the disk diffusion procedure confirmed the some pyrimidine fused quinoline derivatives antimicrobial effect. The results showed that synthesized compounds prevented the bacterial growth. This used procedure for preparation of pyrimidine fused quinoline derivatives has some advantages such as low reaction time, product with high yields, simple separation of catalyst and products. 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. Specially fused N-heterocycles, having privileged motifs like pyrimidine and quinolines, are found in many drugs and bioactive natural products. Hybrid molecules having a pyrimidine ring fused with quinoline are also known as deazaflavins or 5-deazaisoalloxazines. [ABSTRACT FROM AUTHOR]

A simple, efficient, and green, one-pot four-component synthesis of spiro[indoline-3,4′-quinoline] derivatives has been developed from isatin, ethyl cyanoacetate/malononitrile, dimedone, and aniline using green catalyst DABCO and green solvent ethanol. The current method generates good to exceptional yields in a short reaction time and provides a broad substrate scope. This method also works for gram-scale reactions. [ABSTRACT FROM AUTHOR]

2-Pyridone is considered as one of the most famous efficient pharmaceutical compounds. Many approaches were discovered to synthesize 2-pyridone. In this present research, chloroacetylation of benzylamine at simple conditions, EtONa/EtCOONa produced N-benzyl-2-chloroacetamide 2. Compound 2 was allowed to react with different reagents. These reagents are acetylacetone, ethyl cyanoacetate, ethyl acetoacetate, and diethyl malonate, creating 2-pyridone derivatives with a good yield. The structures of the prepared compounds were elucidated by spectral data (IR, 1HNMR, and 13CNMR). The synthesized compound was tested for its antimicrobial activity against the Gram-positive (Staphylococcus aureus) and the Gram-negative (Escherichia coli) bacteria. In addition, the antifungal activities of the compounds were tested against two fungi (Candida albicans and Aspergillus flavus). Molecular docking studies were applied using the Autodock vina method. Theoretical methods prove all the experimental results by using molecular docking using Autodock vina and by ADEMT studies. The docking results represent that compound 20 had the best docking free energy, and it is the effective compound toward the selected bacterial and fungal proteins. ADME studies showed that the only compound 18 could cross the blood–brain barrier, and compound 15 was predicted to be soluble.

The present work described one-pot three-component synthesis of tetrahydro benzo[b]pyran derivatives using Water Extract of Watermelon Fruit Peel Ash (WEWFPA) as a inexpensive grener catalyst. The title compounds were synthesized via the condensation reaction of aromatic aldehyde, dimedone, and ethyl cyanoacetate under microwave irradiation in agro-waste solvent medium and ethanol as a co-solvent. The developed method is simple, rapidity, high yields, pure, low cost, mild reaction condition, evading use of toxic metals and solvent, and the catalyst reusability are the main advantages. The resulting products were isolated by simple workup and recrystallization gave pure compounds. Further, the oxidation and reduction potential of the selected tetrahydrobenzo[b]pyran derivatives were studied using cyclic voltammetry. [ABSTRACT FROM AUTHOR]

Reaction of benzaldehyde (5a) with defined quantities of ethyl cyanoacetate (6) in presence of piperidine was studied. In a neat condition, hexasubstituted cyclohexeneamine (7a) with three ester substituents was formed along with ethyl acrylate (9a); occasionally the triesters (7) were transformed to diesters (8). (7) and (8) had uniquely defined stereochemistry. Many substituted aromatic aldehydes and pyridine-3 and 4-aldehydes exhibited this reaction. Cyclohexenes were also formed in solutions. Mass spectral evidence showed the presence of small percentage of isomeric tri and diesters. Mechanistic and other aspects are discussed. Richly substituted cyclohexene amine esters are attractive substrates for medicinal chemistry.

A green synthesis of 2-oxo-2H-chromene-3-carbonitriles has been carried out in one step by reacting 2-hydroxybenzaldehydes or 2-hydroxyacetophenones with ethyl cyanoacetate under dual-frequency ultrasonica-tion (ultrasonic bath of 40 KHz and probe of 20 KHz). The compounds were obtained in very high yield, and their structures were confirmed by IR and NMR data. [ABSTRACT FROM AUTHOR]

2‐Amino‐4H‐pyran‐3‐carbonitriles and 2‐amino‐4H‐pyran‐3‐carboxylate derivatives were synthesized under mild conditions in the presence of tungstate sulfuric acid (TSA) as a recyclable solid acid catalyst. Catalytic condensation between 3‐acetylcoumarin, aromatic aldehydes, and malononitrile or ethyl cyanoacetate gave the 2‐amino‐4H‐pyran derivatives. Tungstate sulfuric acid is a low‐cost, nontoxic, and reusable catalyst, which does not require very high temperatures and good to excellent yields were obtained in all cases. The catalyst can be reused for many times without significant loss of its activity. [ABSTRACT FROM AUTHOR]

A three-component condensation of cyclic enaminones, phenylglyoxal hydrate, and ethyl cyanoacetate in EtOH gave a number of 4,5,6,7-tetrahydroindole functional derivatives. The corresponding intermediates, 2,3,4,5,6,7-hexahydroindoles, are formed under mild conditions. Under more severe conditions (heating under reflux in DMF), cleavage of the ethoxycarbonyl group takes place. [ABSTRACT FROM AUTHOR]

One-pot, three-component reactions of the tricyclic isatin 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with variously substituted aryl cyanomethyl ketones and malononitrile, or ethyl cyanoacetate, generates spiro[4H-pyran-3,3'-oxindoles], such as, 2-amino-2'-oxo-6-(phenyl)-5',6'-dihydro-2'H,4'H-spiro[pyran-4,1'-pyrrolo[3,2,1-ij]quinoline]-3,5-dicarbonitrile. [ABSTRACT FROM AUTHOR]

A new strategy for the synthesis of 3-hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-dicyanomethyl-2-oxindoles in a reaction of isatin with ethyl cyanoacetate by Krapcho dealkoxycarbonylation reaction in aqueous media is demonstrated. The reaction provides an easy access to synthetically and medicinally valuable oxindole alkylnitriles in good to very good yields. Wider substrate scope and operationally simple experimental procedures are highlighted features of the developed protocol. Based on control experiments, a plausible mechanism of reaction and synergistic effect of water is also rationalized. [ABSTRACT FROM AUTHOR]

2 H -Oxo-chromenyl acrylates and 2 H -imino-chromenyl acrylonitriles have been prepared from a salicylaldehyde and ethyl cyanoacetate or 2-amino-1,1,3-tricyanopropene, respectively. The reaction occurs in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) and the products were isolated in good to quantitative yields. Despite the simplicity of the synthesis, this is the first time that these substituted chromenes have been isolated. [ABSTRACT FROM AUTHOR]

Gewald reaction of 4-oxo-1-phenylcyclohexane-1-carbonitrile with ethyl cyanoacetate and elemental sulfur in the presence of diethylamine afforded ethyl 2-amino-6-cyano-6-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate which was treated with a series of acid chlorides to obtain the corresponding 2-amido derivatives. Condensation of the latter with hydrazine hydrate gave new fused benzothienopyrimidines. The synthesized compounds were screened for antioxidant activity. [ABSTRACT FROM AUTHOR]

Quantitative multicomponent cyclocondensation of 3-acetyl-4-hydroxycoumarine with ethyl cyanoacetate and aryldehydes has been carried out in ammonium acetate, at reflux. Quantitative multicomponent cyclocondensation of 3-acetyl-4-hydroxycoumarine with ethyl cyanoacetate and aryldehydes has been carried out in ammonium acetate, at reflux. The optimization details of the developed novel protocol are recorded. The structure of newly synthesized compounds have been characterized by spectroscopic data (elemental analysis, IR and 1H NMR spectroscopic studied). Antimicrobial properties of the novel coumarins derivatives 3 are investigated. The acetylcholinesterase inhibition activity (AChEI) was tested for all compounds, and the 3b shows the highest AChEI activity with 48.25% of inhibition. [ABSTRACT FROM AUTHOR]

The ultimate goal in this paper has been developed for the synthesis of structurally various bromomethyl cyclopropane via an α-bromoketone and/or aldehydes with ethyl cyanoacetate or malononitrile and cyanogen bromide (BrCN) in the presence of Et3N to give products in excellent yields within about 3 s. All structures were characterized by IR, 1H-NMR, 13C-NMR, and Mass spectroscopy techniques. The reaction mechanism was discussed. [ABSTRACT FROM AUTHOR]

Introduction: A novel series of chromen-3-yl-pyridine moieties were synthesized. IR, NMR, and MS spectroscopy were used to confirm the structure of these novel compounds and study antitumor activity of these compounds. The structure-activity relationship investigation demonstrated that 2,4-diamino- 5-(3-methoxyphenyl)-7-(2-oxo-2H-chromen-3-yl)-1,8-naphthyridine-3-carbonitrile (16), naphthyridine- 3-carbonitrile derivatives 17, 18 and pyrido[2,3-d]pyrimidine derivative 12 were found to be more effective, while compounds 5a,b, 9c, 11, 13 and 14 showed moderate activity for antitumor activities., Objectives: The objective was to design a series of new chromen-3-yl-pyridine and pyrido[2,3-d]pyrimidine derivatives and study the antitumor of these compounds., Materials and Methods: The condensation reaction of 3-acetyl-2H-chromen-2-one with 3-methoxy benzaldehyde and malononitrile or ethyl cyanoacetate in the presence of ammonium acetate and acetic acid under reflux to give the corresponding chromen-3-yl pyridine-3-carbonitrile derivatives., Results: In this study, the antitumor activity of the synthesized compounds chromen-3-yl-pyridine derivatives has been determined for the broad spectrum of cytotoxic activity toward the investigated three cell lines and 5-Fluorouracil, as reference drugs., Conclusion: A series of new chromen-3-yl-pyridine and pyrido[2,3-d]pyrimidine derivatives were synthesized in this work. All compounds were evaluated for cytotoxic activity., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

Graphical abstract Highlights • Niobium in MCF as stabilizer for active aminoorganosilane (AP) species. • Gold as activators in Knoevenagel condensation with 2,4-dichlorobenzaldehyde. • (Au°)σ− and Auσ+ can interact with chlorine atoms and aldehyde oxygen atoms. • Gold dopants do not influence the Knoevenagel condensation with benzaldehyde. Abstract The Knoevenagel condensation with chlorine substituted benzaldehyde is difficult because of deactivation of aldehyde group. In this work we have shown that the activity of mesoporous cellular foams (MCF and Nb/MCF), modified with 3-aminopropyl-trimethoxysilane (AP) as a source of basicity, can be enhanced for this reaction by the anchoring of gold species. Gold species were loaded on amine modified materials towards Au/AP-MCF and Au/AP-Nb/MCF. Moreover, copper was used as a dopant for the latter sample giving rise to AuCu/AP/MCF. All these materials were characterized in details by different complementary techniques (N 2 adsorption isotherms, TEM, UV–vis, TG/DTA, XPS, DFT calculations) which allowed the evaluation of states of all components of the catalysts. The interaction between niobium species and AP was evidenced to increase the stability of the basic modifier. This interaction was weakened by the introduction of gold and copper. The presence of both, negatively charged gold nanoparticles (NPs) and gold cations was crucial for the activation of 2,4-dichlorobenzaldehyde via the interaction with chlorine substituent atoms and aldehyde oxygen atoms as well as breaking of the "pseudo hydrogen bond" between aldehyde hydrogen atom and chlorine substituent, which destabilized the structure making it more active. Gold dopants did not influence significantly the condensation of ethyl cyanoacetate with benzaldehyde. [ABSTRACT FROM AUTHOR]

Abstract: An efficient and sustainable method was developed for the electrocatalytic synthesis of nano-sized 4H-pyran derivatives via a green, one-pot, three-component condensations of cyclic-1,3-diketones [including 1H-indene-1,3(2H)-dione, cyclohexane-1,3-dione, cyclopentane-1,3-dione, pyrimidine-2,4,6(1H,3H,5H)-trione], malononitrile or ethyl cyanoacetate, and isatins in an undivided electrochemically cell applying potassium bromide as the electrolyte in the alcoholic media. This electrosynthesis was introduced as a reliable and cost-effective approach for the high-yielding synthesis (76-92%) of the target compounds. The synthesized 4H-pyran and chromene nanoparticles could open an effective way for production of nano-sized drugs.Graphical abstract: [ABSTRACT FROM AUTHOR]

We have demonstrated three component reaction of isatin, enaminone and ethyl cyanoacetate leading to sprirooxindole scaffold without catalyst in water. The synthetic protocol has several advantages like wide substrate scope, atom-economy and operationally simple experimental procedures which provides rapid access to library of compounds. The mechanistic details of the reaction has been investigated during the course of study. [ABSTRACT FROM AUTHOR]

Abstract: In this paper, boron trifluoride supported on coconut shell nano-particles (nano-BF2O-coc) was prepared from nano-crystalline coconut shell through mechanical method using ultrasonication. The resultant was utilized to obtain nano-crystalline BF3 supported on coconut shell nano-particles (nano-BF2O-coc). The novel nanostructure has been characterized using Fourier transform infrared spectroscopy, transmission electron microscopy, field-emission scanning electron microscopy, and energy-dispersive X-ray spectroscopy (EDX) techniques. The catalytic activity of the solid acid catalyst has been successfully examined in a one-pot, three-component condensation reaction of barbituric acid, ethyl cyanoacetate or malononitrile, and aldehydes in refluxing ethanol to furnish pyrano[2,3-d]pyrimidine derivatives.Graphical abstract: [ABSTRACT FROM AUTHOR]

Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75-100% yield. [ABSTRACT FROM AUTHOR]

The conjugate hydrocyanation of chalcone derivatives using ethyl cyanoacetate as an organic cyanide source at room temperature under open air and transition metal-free conditions was described. The protocol has advantages of using relatively cheap, less toxic, stable and easy-to-handle cyanating reagent, high yield, and mild reaction condition. [ABSTRACT FROM AUTHOR]

New N-glycosides based on valproic acid analogs tetrazole derivatives were synthesized. The bis-tetrazole derived from 1,6-hexandiol was also connected to acetylated glucose and formed bis- N-glycoside. Structures characterizations have been performed using FT IR, H and C NMR spectroscopy. [ABSTRACT FROM AUTHOR]