Presence Of Triethylamine Research Articles

Microwave-Assisted Synthesis and Antimicrobial Activity of Novel Azetidinones from Dehydroacetic Acid

This paper describes the reaction of dehydroacetic acid with primary aromatic amines to yield Schiff bases (2a-2g) by using microwave system. Schiff bases irradiated with dimethyl formamide in presence of triethyl amine and chloroacetyl chloride to afford azetidinones (3a-3g) in excellent yields. The products, characterized on the basis of spectral data, have shown moderate to good antimicrobial activity against some bacteria and fungi.

Rhodium‐Catalyzed Reductive Hydroformylation of Polyunsaturated Vegetable Oils Assisted by Triethylamine/N‐methylimidazole Ligands Combination

AbstractIn this work, the reductive hydroformylation of linseed and sesame oils was carried out successfully by using a rhodium catalyst precursor associated to triethylamine/N‐methylimidazole ligands combination. Interestingly, in the presence of triethylamine and N‐methylimidazole at a precise ratio with respect to rhodium, the isomerization reaction can be inhibited and control experiments realized on methyl linoleate and methyl linolenate have clearly shown that no conjugated products were formed. This new catalytic system is full of interest since the yields in alcohols, after 24 h, are equal to 21% and 15% for Rh/triethylamine combination, whereas equal to 58% and 63% for Rh/triethylamine/N‐methylimidazole combination, for linseed and sesame oils, respectively.

Synthesis, mechanistic insights, and anticancer evaluation of novel 2-aroylbenzo[b]thiophen-3-ols: A DFT and Hirshfeld surface analysis

A simple one-pot reaction was employed for the synthesis of 2-aroylbenzo[b]thiophene derivatives by reacting 2-mercaptobenzoic acid with substituted bromomethyl aryl ketones in the presence of triethylamine and DMF in significant yield and purity. The structure of the product was elucidated through spectroscopic data and confirmed through single crystal X-ray diffraction data. The benzo[b]thiophene ring was found to be nearly coplanar with the adjacent carbonyl group and conformationally stabilized by intramolecular hydrogen bonding. The key intramolecular cyclization takes place via an in-situ generated enol, which is most likely formed and reacts at the carboxylic group mediated by the conjugate acid, triethylammonium bromide. Density functional theory (DFT) was employed to investigate the energy profile of the reaction at the B3LYP/6–31G(d,p) level. Finally, all the synthesized 2-aroylbenzo[b]thiophene-3-ols were screened in vitro against HCT116 (colorectal) and MCF-7 (breast) cancer cell lines at 25 μM and 50 μM treatments, indicating the antiproliferative potential of several derivatives.

Self-assembly of tetra nuclear lanthanide (Pr, Nd) hydroxo clusters with functionalized β-diketone: Experimental and theoretical studies

Reaction of LnCl3·6H2O (Ln = Pr, Nd) with functionalized β-Diketone {ortho-hydroxydibenzoylmethane (HO-DBM)} in 1:2 ratio in methanol and in presence of triethylamine (excess) as base yielded two tetra nuclear lanthanide hydroxo clusters of composition [Ln4(O-DBM)4(HO-DBM)4(µ3-OH)2][Et3NH]2.3CH2Cl2, (Ln = Pr (1), Nd (2)). The clusters 1 and 2 has been structurally characterized by single crystal X-ray diffraction. A one-dimensional supramolecular chain is observed in the solid state structure (2), where dichloromethane solvent molecules are linked to the phenyl rings of adjacent diketone linkers through CH⋯π and Cl⋯π interactions. Theoretical studies support the stability of structure (2), with calculated geometric parameters aligning with experimental findings.

Organotin(IV) complexes anchored on the magnetic UiO-66-NH2 metal–organic framework: Synthesis and evaluation of cytotoxicity

The magnetic metal–organic framework nanocomposite Fe3O4@UiO-66-NH2 was prepared and reacted first with 5, 5′-methylene bis-salicylicaldehyde and then benzhydrazide. In this way, a hydrazone ligand is loaded on the nanocomposite. This functionalized magnetic MOF was reacted with R2SnCl2 (R = Ph, Me) in the presence of triethylamine; thus organotin(IV) complex was immobilized on nanostructures (Fe3O4@UiO-66-SnR2). In order to increase cellular uptake, MOF-based magnetic nanocomposites carrying organotin(IV) complex were also modified by folic acid (Fe3O4@UiO-66-SnR2-FA). All synthesized nanomaterials were characterized using FT-IR, FE-SEM, HRTEM, EDX, XRD, VSM, and TGA techniques. Then, the in vitro cytotoxicity of nanocomposites as well as free hydrazonic ligand and organotin(IV) complexes were evaluated against HT-29, A549 and Hela cell lines using the MTT method. Based on the results, folate-modified targeted systems show more cytotoxic activity than others, and the highest activity was observed for Fe3O4@UiO-66-SnPh2-FA against HeLa cells.

Identification of imidazo[1,2-a]pyridines-pyrazole-pyran hybrids as potent glucose-6-phosphate dehydrogenase (G6PD) inhibitors: Synthesis, molecular docking, DFT studies and ADME prediction

In this study, we aimed to identify new anticancer agents by synthesizing a series of Imidazo[1,2-a]pyridines fused with pyrazole-pyran scaffolds 7a–g in good yields (75–85 %) under microwave irradiation. The synthesis was performed through a one-pot, three-component cyclocondensation reaction of 2-(p-substituted)imidazo[1,2-a]pyridine-3-carbaldehyde 4a-g, malononitrile 5, and 5-methyl-2,4-dihydro-3H-pyrazol-3-one 6 in the presence of triethylamine as a catalyst in acetonitrile. The characterization of all synthesized compounds was accomplished through various spectroscopic techniques. All the synthesized compounds were investigated for their anticancer potential in vitro, using an MTT-based assay against A549 lung cancer cell lines. Compounds 7b, 7e, and 7c demonstrated notable anti-proliferative activity against the A549 cell line, while compound 7e showed a significantly lower fluorescence generation (24-fold less) in the G6PD inhibition assay compared to the other compounds.

Synthesis and Polymerization of Poly Acryl Imide and One of Their Derivatives Then Curing the Product with Alkyl Halide

The present work involved four steps: First step include reaction of acrylamide ,N-?-Methylen-bis(acryl amide) and N-tert Butyl acryl amide with poly acryloyl chloride in the presence of triethyl amine (Et3N) as catalyst, the second step include homopolymerization of all products of the first step by using benzoyl peroxide(BPO) as initiator in (80-90)Co in the presence of Nitrogen gas(N2). In the third step the poly acrylimide which prepare in second step was convert into potassium salt by using alcoholic potassium hydroxide solution. Fourth step include Alkylation of the prepared polymeric salts in third step by react it with different alkyl halides(benzyl chloride, allylbromide , methyl iodide) by using DMF as solvent for(10-12) hours. Structure Confirmation of all prepared polymers were proved using FT-IR, 1H-NMR and C13-NMR spectroscopy for some polymers. Other physical properties including softening and melting points of the polymers were also measured.

A green and efficient synthesis of alkyl 2-((5-hydroxy-1H-pyrazole-4-carbonothioyl)thio)acetates via a one-pot, solvent-free reaction

A green and efficient synthesis of alkyl 2-((5-hydroxy-1H-pyrazole-4-carbonothioyl)thio)acetates is described. The method involves a one-pot, solvent-free reaction of pyrazolone derivatives, carbon disulfide, and alkyl bromoacetates in the presence of triethylamine. The crude products were readily purified by simple water washing followed by recrystallization from diethyl ether. The structures of the synthesized pyrazole-4-carbonothioyl-thio-acetate derivatives were confirmed by IR, 1H NMR, 13C NMR, and mass spectrometry.

Microwave-assisted synthesis of solketal from glycerol and acetone in the presence of SAPO-34 and SAPO-5

Solketal is one of the most promising additives improving the properties of motor fuels. Investigations related to process intensification of synthesis of solketal from glycerol and acetone is gaining importance. The present work illustrates the use of the microwave mode for intensification of this process in the presence of silicoaluminophosphates (SAPO) as catalysts. The main focus of the study was placed on tuning the textural, acidic, and catalytic properties of SAPO-34 and SAPO-5 via variation of the synthesis parameters, such as the nature of Al and Si sources and the structure-directing agent. The catalytic properties of SAPO materials were investigated in the synthesis of solketal from glycerol and acetone under microwave assistance at the acetone/glycerol molar ratio of 2.4 in a methanol solution (glycerol/methanol: 1 g/1 mL) and 56 °C. It was demonstrated that the selectivity towards solketal was 91.1–98.6 % in the presence of the studied materials. The activities of mesoporous SAPO-34 and SAPO-5 prepared in the presence of triethylamine were higher as compared with microporous SAPO-34 prepared in the presence of tetraethylammonium hydroxide due to the high mesoporosity and a larger content of acid sites. The 90.4 % conversion of glycerol and 98.6 % selectivity towards solketal were observed in the presence of mesoporous 7.6%SAPO-34 for 90 min. The advantage of using microwave technology is shown. The solketal yield in the reaction under microwave irradiation was 3 times higher than that in the process performed under thermal heating conditions.

Base-Promoted Aminoamidation of Cinnamoyl Chlorides with Aryl Amines: Access to β-Amino Amides.

Herein, a base-promoted strategy for the synthesis of β-amino acids derivatives from α,β-unsaturated acyl chlorides derivatives and aryl amines has been described. In the presence of triethylamine, a tandem Michael addition and nucleophilic substitution progress was generated. The current method features readily available raw materials, mild reaction conditions, high atom economy, and wide tolerance for the coupling partners.

Facile synthesis and tunable fluorescent properties of a new D-π-A isocoumarin: Applications in encryption and OLED technology

A facile synthesis of a new D-π-A isocoumarin (ICP-NH2) with only two steps under mild conditions through O-acylation/Wittig/reduction reaction has been established. The readily accessible phosphonium salt precursor 1 and 4-nitrobenzoyl chloride 2 produced intermediate ICP-NO2 in the presence of triethylamine. Subsequently, ICP-NO2 underwent conversion to ICP-NH2 through the reduction of stannous dichloride. ICP-NH2 exhibits enhanced fluorescence overcoming the photo-induced electron transfer (PET) process in ICP-NO2. ICP-NH2 demonstrates a significant change in fluorescence from blue to green in various polar solvents, and DFT analysis confirmed that its solvatochromism is attributed to intramolecular charge transfer (ICT) effect. ICP-NH2 undergoes noticeable acidochromism based on reversible protonation and deprotonation reactions with TFA and TEA, leading to periodic changes in fluorescence from green to dark blue. This phenomenon can be utilized in designing reusable encryption technology. Additionally, ICP-NH2 can be employed in the fabrication of a cyan green OLED device.

Синтез 5-амино-3-арил-1H-пиразол-4-карбонитрилов на основе гидразинов или бензгидразидов в условиях ультразвуковой активации

Pyrazoles containing amino and carbonitrile groups have a wide range of biological activities, including antimicrobial, antiinflammatory, antitumor, antioxidant, and are used to create pesticides and dyes. Also, these compounds are synthons for the preparation of various polyheterocyclic compounds. New potentially biologically active 5-amino-3-aryl-1H-pyrazole-4-carbonitriles containing pharmacophoric substituents have been obtained via three-component condensation reactions of malonic dinitrile with substituted aromatic aldehydes and benzhydrazides or hydrazines. This work considers the limits of applicability of hydrazines and hydrazides as weak nucleophiles in similar processes. The described target compounds have been synthesized using the «green chemistry» approach under ultrasonic activation in water or a mixture of water and isopropyl alcohol in the presence of triethylamine as base catalyst. The applicability of this environmentally friendly, economical and efficient approach for the synthesis of nitrogen-unsubstituted (7, 8) and N-aryl- (4, 6) or N-aroyl-substituted (1–3) pyrazole-4-carbonitriles has been demonstrated. The target pyrazole-4-carbonitrile (2) is formed and Schiff base (2’) is released as a by-product in the reaction of the weak binucleophile 3-nitrobenzhydrazide with 4-benzyloxy-3-methoxybenzaldehyde and malonic dinitrile. Step-by-step syntheses have shown that the initial reaction of a three-component interaction can be either croton condensation or the formation of a Schiff base. In any case, during subsequent heterocyclization, unstable substituted pyrazolines are formed, which aromatize to the target pyrazoles in the presence of atmospheric oxygen under synthesis conditions. The composition and structure of the products have been confirmed by elemental analysis, NMR 1H, 13C spectroscopy, HSQC, and HMBC heteronuclear correlations.

Synthesis, characterization and bioactive evaluation of cobalt(II) and copper(II) complexes of {4-[5-(5-sulfanylidene-2,5-dihydro-1H-1,2,4-triazol-3-yl) furan-2-yl] phenyl} acetic acid

A new triazole derivative was synthesized by three steps. The first step involve adding 2-carboxyaledhyed furan to the 4-amino phenyl acetic acid after converting the substituted aromatic amine to the diazanium salt. In the first stage, [4-(5-formylfuran-2-yl) phenyl] acetic acid is the title of product. The second step is adding the thiosemicarbazide to the [4-(5-formylfuran-2-yl) phenyl] acetic acid which it gives the (4-{5-[(2-carbamothioylhydrazinylidene) methyl] furan-2-yl} phenyl) acetic acid. A final compound with the title {4-[5-(15-sulfanylidene-2,5-dihydro-1H-1,32,4-triazol-3-yl) furan-22-yl] phenyl} acetic acid was produced as a result of adding sodium acetate and chloro ethyl acetate to the product from the second step in the presence of triethyl amine which is used as a ligand to prepare cobalt(II) and copper(II) complexes. The structures of synthesized compounds were identified through the utilization of diverse measures, these measurements were (UV-Vis spectrum, LC-MS technique, FT-IR spectrophotometer, conductivity measurements, GC-mass spectra and atomic absorption) and melting point measurement. The results confirmed that the complexes have octahedral geometry. The biological activity data for the synthesized compounds revealed that the ligand and its complexes had antibacterial activity. KEY WORDS: Synthesis, Triazole derivatives, Cobalt(II) complex, Copper(II) complex, Biological evaluation Bull. Chem. Soc. Ethiop. 2024, 38(6), 1595-1607. DOI: https://dx.doi.org/10.4314/bcse.v38i6.8

Ni(II)/Yb(III)-metallogels for distinctive fluorescent ‘turn-on’ detection of m-phenylenediamine: Toward construction of multiple logic gates

New versatile Schiff base gelator (HL) and its highly selective Ni(II)-and Yb(III)-based metallogels 1–2 have been synthesized and characterized by spectral techniques. Gelator HL in presence of triethylamine (Et3N) with Ni(NO3)2·6H2O and anhydrous Yb(NO3)3 in DMF/MeOH(1:1) solvents forms MG1 and MG2 supramolecular gels, respectively at room temperature (rt). Rheological results show thermal stability up to 100 ℃ and structurally rigid nature of MG1 and MG2. Remarkably, MG1 and MG2 were examined for identification of cations, anions, nitroaromatics and aromatic amines (AAs) but unable to recognize any analytes except for m-phenylenediamine (MPD) by using MG1. Metallogel MG1 shows highly selective response to MPD environmental pollutant with a limit of detection (LoD) of 7.58 × 10-7 M, without any interference of competing analytes. Interestingly, depending upon fascinating fluorescent On-Off-On switching behavior, molecular logic device has been fabricated with AND and IMPLICATION-logic gates function by employing the chemical inputs (i) HB, Ni(II) (MG1), Yb(III) (MG2) and (ii) HB, MG1 and MPD based on emission change at different wavelengths as output signal.

Mixed ligand complexes of Pt(II) Tertiary phosphines and 1-(benzo[d]thiazol-2-yl)-3-phenylthiourea; Crystal structure and DFT of [Pt(C14H9N3S2)(dppe)].CH2Cl2

This paper describes a series of Pt(II) thiourea complexes (1–4). The complexes were synthesized by a reaction between [PtCl2(diphos)] and the ligand 1-(benzo[d]thiazol-2-yl)-3-phenylthioure in the presence of triethylamine, with all reactants present in equimolar amounts. The produced complexes exhibited square planar geometry, which was validated by FT-IR and 1HNMR . Single crystal XRD study revealed that the coordination geometry was distorted square planar in [Pt(Btzt)(dpppe)]. Hirshfeld surface analysis was used to delve deeper into the intermolecular interactions which showed that the combined contribution of H⋯H and H⋯C contacts in the stabilization of the supramolecular assembly was 81.3%. A void analysis was carried out which showed that there was no large cavity in the supramolecular assembly. Theoretical studies were also conducted on [Pt(Btzt)(dpppe)]. The DFT analysis was carried out using the B3LYP Hybrid method in combination with Def2-SVP. The theoretical findings indicated just 3% differences between the theoretical and experimental Figures. Furthermore, the computed HOMO-LUMO gap was 3.4 eV, which was close to the anatase photocatalyst's band gap. DFT predicted that all complexes are non-magnetic with μB=0. There are high electron donation and back-donation between heteroatoms and transition metals in the complexes.

Multicomponent reaction for synthesis, molecular docking, and anti-inflammatory evaluation of novel indole-thiazole hybrid derivatives.

In this article, novel thiazol-indolin-2-one derivatives 4a-f have been synthesized via treatment of thiosemicarbazide (1) with some isatin derivative 2a-f and N-(4-(2-bromoacetyl)phenyl)-4-tolyl-sulfonamide (3) under reflux in ethanol in the presence of triethyl amine (TEA). The structures of new products were elucidated by elemental and spectral analyses. Moreover, all compounds were investigated for their in vivo anti-inflammatory activity using celecoxib as a reference drug. The target compound 4b was the most active anti-inflammatory candidate and exhibited higher edema inhibition (EI = 38.50%) than that recorded by celecoxib (EI = 34.58%) after 3h. Furthermore, the most active compounds 4b and 4f were subjected to a molecular docking study inside COX-2 enzyme to show their binding interactions. Both compounds 4b and 4f showed good fitting into COX-2 binding site with docking energy scores -11.45kcal/mol and -10.48kcal/mol, respectively which indicated that compound 4b revealed the most promising and effective anti-inflammatory potential.

Synthesis, characterization, enzyme inhibition and molecular docking studies of benzothiazole derivatives bearing alkyl phenyl ether fragments

Novel benzothiazole derivatives containing alkyl/benzyl phenyl ether fragments have been synthesized through two step reaction process. Initially, 2-hydroxybenzaldehyde was refluxed with 2-aminothiophenol in the presence of sodium metabisulfite (Na2S2O5) in DMF solvent followed by treating it with alkyl and aromatic halides in the presence of triethylamine in dry acetone to get the product derivatives (1–11) in better yields. These products were characterized by means of modern spectroscopic (1H, 13C NMR and HR-ESI-MS) techniques and screened for in vitro tyrosinase inhibitory activity. In the series, three compounds 13 (IC50 = 8.6 ± 0.2 µM), 3 (IC50 = 11.1 ± 0.5 µM), and 12 (IC50 = 18.2 ± 0.1 µM) showed excellent inhibition comparing with the standard kojic acid (IC50 = 17.8 ± 0.6 µM). Likewise, six compounds 9, 10, 11, 2, 4, and 5 attributed significant activity ranging from IC50 22.6 ± 0.8 to 29.2 ± 0.3 µM. Besides, compound 6 (IC50 = 40.6 ± 0.5 µM) was found least active while two compounds 7 and 8 were found inactive. The molecular docking study on molecules and their interaction with tyrosinase protein revealed a consistent pattern in the activity of kojic acid. The electronic characteristics of active derivatives 2, 3, 9–12, and kojic acid were examined using the TD-DFT approach. The study found that the HOMO and LUMO were concentrated on the π-conjugated system of the benzothiazole rings moiety, indicating a significant delocalization of electrons. The study also found that compounds compared to kojic acid, possess chemical hardness and stability properties, with lower electrophilicity index indicating higher bioactivity and lower toxicity. The study also highlighted the importance of comprehensive ADMET profiling in early drug development to ensure safety and efficacy.

A Novel One-Pot Three-Component Approach to Orthoaminocarbonitrile Tetrahydronaphthalenes Using Triethylamine (Et_3N) as a Highly Efficient and Homogeneous Catalyst Under Mild Conditions and Investigating Its Anti-cancer Properties Through Molecular Docking Studies and Calculations

An efficient and environmentally friendly method for the one-pot synthesis of ortho-aminocarbonitrile tetrahydronaphthalenes has been developed in the presence of triethylamine (Et3N) as a homogeneous catalyst. The multicomponent reactions of benzaldehydes, cyclohexanone and malononitrile were carried out under mild conditions to obtain some ortho-aminocarbonitrile tetrahydronaphthalene derivatives. A broad range of structurally diverse benzaldehydes were applied successfully, and corresponding products (4A-L) were obtained in good to excellent yields (87-98%) in very short times (10-25 minutes). The present approach provides several advantages including simple workup, high yields, very mild reaction conditions, short reaction times, little catalyst loading and not requiring specialized equipment. Furthermore, with the help of computational chemistry and drug design methods, the anti-cancer properties of these compounds were studied and investigated. All the synthesized compounds bind to an agonist at the active site of the 3A8P protein, which leads to the inactivation of this protein and produces beneficial effects during cancer treatment. In synthesized compounds, the ligands establish hydrogen bonds with leucine A:728 residues through nitrogen, which has a very special and vital role in biological sciences and pharmaceutical connections. In this study, it was found that these compounds have the potential to become an oral anti-cancer drug.

Deconvoluting Substrates, Support, and Temperature Effects on Leaching and Deactivation of Pd Catalysts: An In Situ Study in Flow.

Leaching behavior of three different Pd heterogeneous catalysts (PdEnCat 30, FibreCat FC1001, and Pd/Al2O3) during the Heck reaction of iodobenzene and methyl acrylate, in the presence of triethylamine, was compared using a tandem flow reactor. While leaching was observed in all three cases, Pd/Al2O3 appeared to be the most robust, showing little/no leaching at ambient temperature. The leached Pd species also appear to display different catalytic activities. With a slight modification of the reactor, the leaching caused by individual components of the reaction mixture can be assessed separately. For the polymer-supported catalysts, triethylamine caused the largest amount of leaching, even at 30 °C. In contrast, the leaching from Pd/Al2O3 was observed only in the presence of iodobenzene at 90 °C. Variations in leaching behavior were ascribed to differences in Pd species and immobilization methods.

Synthesis of Mesylated and Tosylated α-Hydroxy-Benzylphosphonates; Their Reactivity and Cytostatic Activity.

α-Hydroxyphosphonates and their acylated and phosphorylated derivatives may be of significant biological activity including cytotoxic effects. To extend the pool of the potentially bioactive species, new methane- and arenesulfonyloxyphosphonates were synthesized by the sulfonylation of differently substituted α-hydroxy-benzylphosphonates using methanesulfonyl chloride or p-toluenesulfonyl chloride at 25 °C in the presence of triethylamine in toluene. The new sulfonyl derivatives were obtained in 54-80% yields. In the case of the 4- or 2-methoxy substituent in the aromatic ring, surprisingly the corresponding α-chlorophosphonates were the exclusive products, whose formation was explained assuming a quinoid intermediate and supported by theoretical calculations. With a 3-methoxyphenyl substituent, the expected mesylation of the hydroxy group took place. Attempted alcoholyses of the diethyl α-methanesulfonyloxy-benzylphosphonates with different substituents in the benzyl ring at ∼140 °C in the presence of triethylamine under microwave irradiation left the P-function intact under the conditions applied, instead, the mesyloxy group was substituted by an alkoxy unit in a selective new reaction. The α-alkoxy-benzylphosphonates were isolated in 60-77% yields. While α-chloro- or α-bromo-benzylphosphonates proved to be rather inefficient in the Michaelis-Arbuzov reaction with triethyl phosphite, according to a new possibility, the α-methansulfonyloxy-benzylphosphonates underwent an efficient Arbuzov fission using the phosphite in excess at 135 °C. The arylmethylenebisphosphonates were obtained in yields of 76-81%. Bioactivity studies with the members of the phosphonate library revealed pronounced in vitro cytostatic effect of the α-hydroxy- and α-mesyloxy-3,5-di-tert-butylbenzylphosphonates on human breast carcinoma cell culture with IC50 values of 16.4 and 28.0 μM, respectively. The mesyloxy species was also cytostatic on melanoma cells (IC50 = 34.9).