Synthesis Of Ethyl Research Articles

The synthesis of ethyl 2-amino-1-(aryl)-5-(arylcarbamoyl)-6-oxo-1,6-dihydropyridine-3-carboxylates

The synthesis of ethyl 2-amino-1-(aryl)-5-(arylcarbamoyl)-6-oxo-1,6-dihydropyridine-3-carboxylates

Effect of Laterally Substituted Methoxy Group on the Liquid Crystalline Behavior of Novel Ester Molecules

Background: The aim of this research is to study the effect of length-to-width ratio on mesomorphism to enhance the understanding of its potential applications. This will be achieved by synthesizing a unique and innovative series of identical ester molecules, including lateral methoxy groups and terminal ethyl benzoate groups. In this research, we aim to find new insights into the relationship between molecular structures and mesomorphic behaviors, which could have significant implications for the development of advanced materials with adapted properties. : The objective of the study is to investigate the mesophase behavior of new ester mesogens and determine how they are influenced by lateral methoxy groups. By identifying the underlying perspectives and relationships between these variables, we hope to better understand the unique properties and potential applications of these materials. Method: In this research work, the focus is on the synthesis of ethyl(E)-4-((3-(4-alkoxy-3- methoxyphenyl)acryloyl)oxy)benzoate, which is prepared from Steglich esterification method by using (E)-3-(4-alkoxy-3-methoxyphenyl)acrylic acid and ethyl 4- hydroxybenzoate. Synthesis processes involve precise reaction sequences designed to ensure maximum yield and purity of the final product. By providing a detailed report on the experimental process, this study contributes to the ongoing research efforts aimed at the development of innovative compounds with various applications in liquid crystals Result: A new set of liquid crystal derivatives has been synthesized and studied to investigate the effect of molecular structure on the behavior of liquid crystals, with particular attention to the group -OCH3 located laterally. This series was composed of 12 derivatives (C1-C16). Among them, the first six derivatives (C1-C6) did not have the characteristics of a liquid crystal, while the remaining derivatives (C7 and C8) had a monotropic behavior, and C10-C16 had an enantiotropic smectogenic liquid crystal behavior without exhibition of the nematic phase. The average thermal stability of the smectic property was 87.33 °C, and the mesophase range was 2 °C to 14 °C. The molecular structure was confirmed by analytical and spectral analysis. The properties of liquid crystals of this new series were compared with those of other known structurally similar homologous series. The transition temperatures were determined with an optical polarizing microscope equipped with a heating phase. Conclusion: The mesomorphic thermal and optical properties of the compounds have been validated by DSC and POM techniques. The result shows that the length of the alkyl chain has a significant influence on the mesomorphic characteristics and thermal stability of the different mesophases. Evaluation of the compounds studied indicates that the molecules are sensitive to their lateral substituent, which influences the thermal characteristics and stability of the mesophase.

Synthesis of ethyl 2-methyl-4-(diethoxyphosphoryl)4,7-dihydro-5<i>H</i>-thiopyrano[3,4-<i>b</i>]furan-5-carboxylate and its functionalization at the position 3

Ethyl 2-methyl-4-(diethoxyphosphoryl)-4,7-dihydro-5 Н -thiopyrano[3,4- b ]furan-5-carboxylate was synthesized. It was shown that at elevated temperatures it is acetylated in presence of tin tetrachloride and chloromethylated with paraformaldehyde-hydrogen chloride system in the presence of zinc dichloride at the positon 3 of heterocyclic system. Reaction of chloromethyl derivative with N -, S - and О -nucleophiles were studied.

Molecular Dynamics Simulation, QSAR, DFT, Molecular Docking, ADMET, and Synthesis of Ethyl 3-((5-Bromopyridin-2-yl)Imino)Butanoate Analogues as Potential Inhibitors of SARS-CoV-2

Structural modifications of ethyl-3-((5-bromopyridin-2-yl)imino)butanoate ester enhances its biological activities. In the present work, the synthesis of a Schiff base by reacting 2-amino-5-bromo pyridine and ethyl acetoacetate was reported. Electronic properties were investigated by the computational method of density functional theory (DFT). The pass prediction score supported anti-viral efficacy which satisfied the Lipiniski rule and overall HOMO-LUMO. The most important part of this investigation was docking study which revealed that the ligands L07 has nearly efficacy to standard drugs and maximum docking score was found against Alpha variant (7EKF) at −6.7 kcal/mol, Beta variant (7ekg) at −6.2 kcal/mol, Gamma variant (7EKC) at −6.5 kcal/mol, Beta variant (7ekg) at −6.2 kcal/mol, SARS-CoV-2 Gamma variant (7EKC) at −6.2 kcal/mol, Delta variant (7V8B) at −6.1 kcal/mol and Omicron variant (7T9J) at −6.3 kcal/mol. Finally, molecular dynamics study was performed to determine the stability and it was reported that the molecules L07 has better stability to be an oral drug against the different variant of SARS-CoV-2 viral pathogen.

Biginelli reaction in the synthesis of ethyl 4-(6-aryl-5-benzoyl-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxamido)benzoates

Three-component Biginelli reaction of ethyl 4-(2,4-dioxo-4-phenylbutanamido)benzoate, aromatic aldehyde and thiourea in acetic acid in the presence of sodium acetate led to the formation of ethyl 4-(6-aryl-5-benzoyl4-hydroxy-2-thioxohexahydropyrimidine-4-carboxamido)benzoates. Structure of the obtained compounds was established by IR, 1H NMR, 13C spectroscopy methods.

Synthesis of ethyl 4-(2-fluoro-4-nitrophenoxy) picolinate

Cancer has seriously affected people's production and life. The appearance of anti-cancer drugs has brought good news to people. Ethyl 4-(2-fluoro-4-nitrophenoxy) picolinate is an important basic skeleton of a small molecule inhibitor of c-Met and a major intermediate in cancer therapy. A rapid and efficient method for the synthesis of compound 8 was established. Compound 8 was synthesized from picolinic acid by acylation and substitution. These steps were weight gain reaction. The synthesis method was optimized and the structure was confirmed by hydrogen NMR spectroscopy.

Features of the Reaction of 5-aminoisoxazoles with diethyl 2-oxosuccinate. Synthesis of ethyl 6-hydroxy-isoxazolo[5,4-b]pyridine-4-carboxylates

Features of the Reaction of 5-aminoisoxazoles with diethyl 2-oxosuccinate. Synthesis of ethyl 6-hydroxy-isoxazolo[5,4-b]pyridine-4-carboxylates

Synthesis of ethyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-4H/2H-chromene-3-carboxylates by cycloaddition of ethyl 2-(azidomethyl)-4H-chromene-3-carboxylates with alkynes

The cycloaddition reaction has been carried out between ethyl 2-(azidomethyl)-4H-chromene-3-carboxylates and phenylacetylenes/ activated alkynes. Phenylacetylene, 4-fluorophenylacetylene were provided mixture of 2H- and 4H-triazolylchromene-3-carboxylates, whereas methyl, methoxyphenylacetylene and acetylenedicarboxylates were provided exclusively 2H-triazolylchromene-3-carboxylates. Interestingly, prop-2-yn-1-ol and ethyl propiolate were provided exclusively 4H-triazolylchromene-3-carboxylates.

Agro-Waste Sourced Catalyst as an Eco-Friendly and Sustainable Approach for Knoevenagel Condensation Reaction

Background: The present work describes an eco-friendly and sustainable approach for the Knoevenagel condensation of an aromatic aldehyde with ethyl cyanoacetate, and salicylaldehyde with Meldrum acid for the synthesis of ethyl benzylidenecyanoacetate and 3-carboxy coumarin (2-oxo-2H-1-benzopyran) derivatives, respectively. The reaction was performed under green catalytic media-Water Extract of Watermelon Fruit Peel Ash (WEWFPA), which is an eco-friendly protocol derived from the agro-waste feedstock. Various protocols have been reported for the synthesis of Knoevenagel condensation reaction using a hazardous catalyst or/and solvents found toxic to the environment, requiring longer reaction time, giving poor yield, and requiring purification of the final product. The method at hand provides several added advantages like: being a completely green method, economic, inexpensive catalyst, and the final product isolated is in pure form with good yield. Objective: The objective of the study was to develop a green methodology for the synthesis of ethyl benzylidenecyanoacetate and 3-carboxy coumarin derivatives. Results: The agro-waste based catalyst developed in the present study avoids the use of external inorganic/ organic bases and additives. Knoevenagel condensation of ethyl benzylidenecyanoacetate and 3-carboxy coumarin derivatives is carried out under room temperature using microwave irradiation, which is a solvent-free synthesis, requiring less time and giving better yield. Methods: We have demonstrated that WEWFPA can be employed as a green homogenous agrowaste for the synthesis of ethyl benzylidenecyanoacetate and 3-carboxy coumarin derivatives under rt stirring and microwave irradiation in a very economical way. The developed method is found to be simple and robust, non-hazardous and solvent-free to obtain the target product. Conclusion: In conclusion, we have established an efficient, simple, agro-waste based catalytic approach for the synthesis of ethylbenzylidenecyanoacetate and 3-carboxy coumarin derivatives employing WEWFPA as an efficient catalyst under rt stirring and microwave synthesis. The method is a green, economical and eco-friendly approach for the synthesis of Knoevenagel condensation products. The advantages of the present approach are that the reaction is a solvent-free synthesis, requiring no external metal catalyst, chemical base free, short reaction time and excellent yield of product. The catalyst is agro-waste derived, which is abundant in nature, thus making the present approach a greener one.

Synthesis of Ethyl 2-(4-halobenzyl)-3-oxobutanoate and determination of its Biological activity by using prediction of activity spectra for substance

In this study, Synthesis of ethyl 2-(4-halobenzyl)-3-oxobutanoate was carried out by using addition of substituted benzyl bromide to a suspension of t-BuOK (Potassium tert-butoxide) in THF (tetrahydrofuran). The reaction mixture was then refluxed for 12 hr. The progress of reaction was monitored using thin layer chromatography (TLC). Synthesize compound are characterized by elemental analysis and spectral analysis like infra red spectroscopy, nuclear magnetic spectroscopy and mass spectroscopy (IR,1H-NMR, MS). Pharmacological activity of these compound were predicted by individually using prediction of activity spectra for substance (PASS). It shows various pharmacological activities and mechanism of action such as L-glucuronate reductase inhibitor, Gluconate 2-dehydrogenase (acceptor) inhibitor, Centromere associated protein inhibitor, Eye irritation, inactive, GST A substrate, Pectate lyase inhibitor, 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase inhibitor, Acetylcholine neuromuscular blocking agent, Antihypoxic, Aspulvinone dimethylallyl transferase inhibitor.

Palladium catalyzed molecular cascades for the synthesis of ethyl 2-methyl-2-(4-methyl-3-(morpholinomethyl)-2-oxopent-3-en-1-yl)-1-oxo-1,2,3,4,5,6-hexahydro-3aH-indene-3a-carboxylate

Palladium catalyzed molecular cascades for the synthesis of ethyl 2-methyl-2-(4-methyl-3-(morpholinomethyl)-2-oxopent-3-en-1-yl)-1-oxo-1,2,3,4,5,6-hexahydro-3aH-indene-3a-carboxylate

Regenerated coenzyme-based preparation of bienzyme-polymer nanoconjugates and their applications for the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate

Regenerated coenzyme-based preparation of bienzyme-polymer nanoconjugates and their applications for the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate

Core‐Shell Faujasite@Aqueous Miscible Organic‐Layered Double Hydroxides Composites with Tunable Acid/Base Properties for One‐Pot Synthesis of Ethyl trans‐α‐Cyanocinnamate

AbstractBifunctional acid‐base catalysts have been developed by fabricating core‐shell faujasite@aqueous miscible organic‐layered double hydroxides (FAU@AMO‐LDHs) composites via the growth of AMO‐LDHs on zeolite surfaces. Interestingly, by adjusting the acid/base properties of the composites, the one‐pot synthesis of ethyl trans‐α‐cyanocinnamate via deacetalization‐Knoevenagel reaction can be achieved up to 90% yield. In contrast, almost no desired products can be observed in cases of isolated zeolites and AMO‐LDHs, demonstrating the synergistic effect of zeolites and AMO‐LDHs as acid‐base catalysts. These findings open up new perspectives of the development of tunable acid‐base zeolite@LDHs composites in an acid‐base tandem reaction, which can selectively produce ethyl trans‐α‐cyanocinnamate up to 90% yield.

Continuous-Flow Processes for the Production of Floxacin Intermediates: Efficient C–C Bond Formation through a Rapid and Strong Activation of Carboxylic Acids

AbstractThe development of highly efficient C–C bond formation methods for the synthesis of ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-(dimethylamino)acrylate 1 in continuous flow processes has been described, which is based on the concept of rapid and efficient activation of carboxylic acid. 2,4-Dichloro-5-fluorobenzoic acid is rapidly converted into highly reactive 2,4-dichloro-5-fluorobenzoyl chloride by treating with inexpensive and less-toxic solid bis(trichloromethyl)carbonate. And then it rapidly reacts with ethyl 3-(dimethylamino)acrylate to afford the desired 1. This process can be performed under mild conditions. Compared with the traditional tank reactor process, less raw material consumption, higher product yield, less reaction time, higher operation safety ensured by more the environmentally friendly procedure, and process continuity are achieved in the continuous-flow system.

Synthesis of ethyl (R)-4-chloro-3-hydroxybutyrate by immobilized cells using amino acid-modified magnetic nanoparticles

Fe3O4-Arg was selected as the optimal carrier due to its high activity recovery of immobilized cells in the preparation of Fe3O4-Arg-Cells. The optimal immobilization conditions for the preparation of Fe3O4-Arg-Cells were 30 °C, 4 h, pH 7, and 3 g dry yeast. The activity recovery of immobilized cells reached 76.8 %. For a batch reduction in a shaker in an alternating magnetic field, Fe3O4-Arg-Cells were used as a catalyst to gain ethyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE). For further improvement in reduction productivity, a continuous reduction in the magnetic fluidized bed reactor system (MFBRS) was completed. Under their optimal transformation conditions, it took 24 h for Fe3O4-Arg-Cells to complete the conversion of ethyl 4-chloro-3-oxobutanoate (COBE) (0.8553 mol/L) in the shaker and only 8 h for the batch reduction in an alternating magnetic field. Continuous reduction in MFBRS provided new ideas for the efficient production of (R)-CHBE; 1.5882 mol/L (10 mL) of COBE can be completely converted in 6 h. The conversion and enantiomeric excess (e.e.) of (R)-CHBE were 100 % and above 99.9 % respectively, in the three reaction systems mentioned above.

The ultrasound accelerated solvent-free synthesis of ethyl 7-methyl-5-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate through Biginelli reaction catalyzed by Amberlyst-15

Multi-component reactions (MCRs) played an important role to produce complex molecular structures in a one-step process. Among all MCRs reported, Biginelli reaction was one of the most well-known and used in organic synthesis to constitute pyrimidine scaffolds. Therefore, a solvent-free Biginelli reaction of 2-aminothiazole, benzaldehyde and ethyl acetoacetate catalyzed by Amberlyst-15 (A-15) had attracted us to pay attention and to do research in order to highly obtain a desired product, a frame of thiazolo[3,2-a]pyrimidine being present in many active biological compounds. Amberlyst-15, polystyrene resin regarded as a green acidic solid, available commercial, inexpensive and reusable catalyst had been firstly and successfully developed for solvent-free Biginelli reaction under ultrasound irradiation to form thiazolo[3,2-a]pyrimidine. Most factors which had influenced on the reaction conversion and yield such as the molar ratios between 2-aminothiazole, benzaldehyde and ethyl acetoacetate, the amounts of catalyst A-15, and reaction time had been investigated. Consequently, the yield of ethyl 7-methyl-5-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate had been also found to depend on the amount of the acidic solid catalyst and little excess amounts of the two reactants, e.g. 2-aminothiazole and ethyl acetoacetate. The maximum yield has been obtained 76% after six-hour ultrasound irradiation at 80oC with the molar ratio of 2-aminothiazole : benzaldehyde : ethyl acetoacetate (1.4:1.0:1.4) and 50 mg of catalyst A-15. The results showed that Amberlyst-15 had high capability of recovery and recycling owing to the inconsiderably changes of product yields after two recycle runs.

A solid solution of ethyl and d 3-methyl 2-[(4-meth-yl-pyridin-2-yl)amino]-4-(pyridin-2-yl)thia-zole-5-carboxyl-ate.

The synthesis of ethyl 2-[(4-methyl-pyridin-2-yl)amino)-4-(pyridin-2-yl)thia-zole- 5-carboxyl-ate via the Hantzsch reaction and partial in situ transesterification during recrystallization from methanol-d 4 to the d 3-methyl ester, resulting in the title solid solution, ethyl 2-[(4-methyl-pyridin-2-yl)amino)-4-(pyridin-2-yl)thia-zole-5-carboxyl-ate-d 3-methyl 2-[(4-methyl-pyridin-2-yl)amino)-4-(pyridin-2-yl)thia-zole-5-carboxyl-ate (0.88/0.12), 0.88C17H16N4O2S·0.12C16D3H11N4O2S, is reported. The refined ratio of ethyl to d 3-methyl ester in the crystal is 0.880 (6):0.120 (6). The pyridine ring is significantly twisted out of the plane of the approximately planar picoline thia-zole ester moiety. N-H⋯N hydrogen bonds between the secondary amino group and the pyridine nitro-gen atom of an adjacent symmetry-related mol-ecule link the mol-ecules into polymeric hydrogen-bonded zigzag tapes extending by glide symmetry in the [001] direction. There is structural evidence for intra-molecular N⋯S chalcogen bonding and inter-molecular weak C-H⋯O hydrogen bonds between adjacent zigzag tapes.

Synthesis of Ethyl 2,2-Bis{[(benzoylcarbamothioyl)oxy]methyl}propanoate and Its Complexes with Copper(II) and Cobalt(II) Ions

The structures of ethyl 2,2-bis{[(benzoylcarbamothioyl)oxy]methyl}propanoate and its 1 : 1 complexes with copper(II) and cobalt(II) ions were determined by electronic absorption, IR, and 1H and 13C NMR spectroscopy and elemental analysis. The coordination entity in the complexes includes oxygen and sulfur atoms of the benzoyl and carbamothioyloxy groups of both ligand branches. The copper(II) ion has octahedral configuration with trigonal distortion, and the cobalt(II) ion has five-coordinate square–pyramidal configuration. The thermal behavior of the title compounds was studied by differential scanning calorimetry and thermogravimetric analysis.

Синтез и биологическая активность 3-замещённых 1H-спиро[бензо[<i>h</i>]хиназолин-5,1’-циклогептан]-2,4(3H,6H)-дионов

На базе этил-4’-амино-1’H-спиро[циклогептан-1,2’-нафталин]-3’-карбоксилата (аминоэфир) разработан метод синтеза этил 4’-(феноксикарбониламино)-1’H-спиро[циклогептан-1,2’-нафталин]-3’-карбоксилата. Взаимодействие последнего с первичными аминами привело к получению 3-замещённых 1H-спиро[бензо[h]хиназолин-5,1’-циклогептан]-2,4(3H,6H)-дионов. Конденсацией аминоэфира с м-хлорфенилизоцианатом синтезирован этил-4’-{[(3-хлорфенил)карбамоил)имино]-3’,4’-дигидро-1’H-спиро[циклогептан-1,2’-нафталин}-3’-карбоксилат, который циклизован в 3-(3-хлорфенил)-1H-спиро[бензо[h]хиназолин-5,1’-циклогептан]-2,4(3H,6H)-дион. Показано наличие противоопухолевой и антимоноаминоксидазной активности у синтезированных соединений.

Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System

Bioreductions catalyzed by alcohol dehydrogenases (ADHs) play an important role in the synthesis of chiral alcohols. However, the synthesis of ethyl (S)-4-chloro-3-hydroxybutyrate [(S)-CHBE], an im...