Bis Methyl Research Articles

Novel Areca Nut extract mediated preparation of TiO2 nanoparticles and its catalytic synthesis of 3, 3′- (phenyl methylene) bis-(4-hydroxy-2H-chromen-2-one) derivatives

• Preparation of TiO 2 nanoparticles by Novel Areca nut extract and characterized by using UV-Vis, FT-IR, XRD and SEM with EDAX analyses. • Synthesized 3, 3′- (phenylmethylene) bis-(4-hydroxy-2H-chromen-2-one) derivatives by using biogenic TiO 2 nanoparticles and synthesized compounds were characterized by different spectral techniques like FT-IR, 1 H NMR, 13 C NMR and LCMS studies. • DFT studies of synthesized compounds showed that the HOMO and LUMO plays significant role in knowing the structure-activity relationship. Moreover, electrostatic potential maps of synthesized compounds have shown behavioral reactive sites. • All the studied compounds exhibited good antioxidant, antimicrobial and anti-tuberculosis activities. • Employed biogenic TiO 2 catalyst exhibited best recyclability upto fifth cycle. The present study describes the preparation of Areca Nut extract mediated TiO 2 and its catalytic application for the synthesis of 3, 3′-(phenyl methylene) bis-(4-hydroxy-2H-chromen-2-one) derivatives by conventional multicomponent reaction. The synthesized compounds have been characterized by FT-IR, 1 H NMR, 13 C NMR and mass spectrometric techniques. Computational studies have been carried out to interpret the structural activity relationship of the synthesized compounds using the B3LYP program at 6e311þþ (d, p) basis set. Additionally, the synthesized compounds were screened for their efficacy towards the antioxidant, antimicrobial, and antituberculosis properties. Further, the recyclability of the employed catalyst has been studied.

Influence of the chain extender of a segmented polyurethane on the properties of polyurethane-modified asphalt blends

This paper reviews the influence of the hard segment (HS) chemical structure on the properties of thermoplastic polyurethanes based on dimer fatty acid soft segments, and on their resulting blends with bitumen. Three types of hard segments were used which consist in 4,4′-methylene bis(phenyl isocyanate) (MDI) reacted either with 1,4-butanediol (BDO), 1,4:3,6-dianhydro D-sorbitol (isosorbide) or 2-ethyl-1,3-hexanediol (EHDO). The characterization of thermoplastic polyurethanes (TPUs) containing 13 wt% HS was conducted by differential scanning calorimetry, dynamic mechanical analysis, Hansen solubility parameters measurements and morphology analysis. The use of Hansen solubility parameters combined with thermal and swelling analyses provides information about the quality of phase separation occurring in the neat TPUs. Phase separation depends on the hard segments used and on their ability to self-organize within crystalline structures. Morphology analysis and swelling measurements of the TPU blended with bitumen by fluorescence microscopy show that the swelling of the polymer is highly dependent on the quality of phase separation between soft and hard segments in the pure polymer as well as on the compatibility of these segments with bitumen. Highly phase separated TPUs offer elasticity improvement to the bituminous blend.

Transesterification of Ethyl-10-undecenoate Using a Cu-Deposited V2O5 Catalyst as a Model Reaction for Efficient Conversion of Plant Oils to Monomers and Fine Chemicals.

Transesterification of ethyl-10-undecenoate (derived from castor oil) with 1,4-cyclohexanedimethanol over a recyclable Cu-deposited V2O5 catalyst afforded 1,ω-diene, the corresponding cyclohexane-1,4-diylbis(methylene) bis(undec-10-enoate), a promising monomer for the synthesis of biobased polyesters, in an efficient manner. Deposition of Cu plays an important role in proceeding the reaction with high selectivity, and both the activity and the selectivity are preserved for five recycled runs by the addition of the substrates. The present catalyst was effective for transesterification with other alcohols, especially primary alcohols, demonstrating a possibility of using this catalyst for efficient conversion of plant oil to various fine chemicals.

Fenugreek seed mucilage grafted poly methacrylate pH-responsive hydrogel: A promising tool to enhance the oral bioavailability of methotrexate

This study aimed to develop the Fenugreek seed mucilage-based pH-responsive hydrogel system in order to improve the oral bioavailability of methotrexate (MTX). Fenugreek seed mucilage (FSM) was extracted from Trigonella foenum-graecum seeds. F1-F9 formulations of pH-responsive hydrogels were prepared using various FSM ratios, methacrylic acid (MAA), and methylene bis acrylamide (MBA) via free radical polymerization technique. Swelling behavior and in vitro drug release studies of prepared hydrogels were evaluated. Toxicity studies of prepared hydrogels were performed on normal cells and on Wistar rats (n = 6). Moreover, in vivo pharmacokinetics parameters were studied on albino rabbits. Hydrogels formation was confirmed by FTIR analysis, thermal analysis and SEM studies. The maximum swelling of hydrogel was found to be 384.7% at pH 7.4. MTX-loaded hydrogel showed the controlled release of MTX up to 24 h following Super Case II transport. Prepared hydrogels exhibited no toxicity in normal cells as well as in experimental subjects. MTX loaded hydrogels exhibited less inhibition compared to free MTX on Hela cells. In Vivo studies revealed 7.5-fold improved oral bioavailability of MTX with higher Cmax (928 ng/mL). These results indicate that the pH-responsive hydrogel system based on FSM is a promising tool for the controlled delivery of MTX.

Process Optimization for Development of Guar Gum-Based Biodegradable Hydrogel Film Using Response Surface Methodology.

In the current study, a guar-gum-based biodegradable hydrogel film was prepared using an initiator (potassium persulfate), crosslinker (N-N methyl bis acrylamide), and plasticizer (glycerol) for packaging of fruits and vegetables. The effect of independent variables (initiator, crosslinker, and plasticizer) on the biodegradation (% wt. loss), color difference (ΔE), hardness (N), swelling index (%), and transparency (%) of the film was studied using Box–Behnken design, random surface methodology (RSM). The results showed significant effects on all the abovementioned parameters, and it was observed that the developed model was accurate, with a prediction error of only −3.19 to 2.99%. The optimized formulation for the preparation of hydrogel film was 0.15% initiator, 0.02% crosslinker, and 2.88% plasticizer exhibiting satisfactory biodegradability, color difference, hardness, swelling index, and transparency. Results showed that a guar-gum-based biodegradable hydrogel film has adequate physical, optical, and biodegradable properties and can be successfully utilized in the food packaging industry.

The Thermo-Oxidative Behavior of Cotton Coated with an Intumescent Flame Retardant Glycine-Derived Polyamidoamine: A Multi-Technique Study

Linear polyamidoamines (PAAs) derived from the polyaddition of natural α-amino acids and N,N′-methylene bis(acrylamide) are intumescent flame retardants for cotton. Among them, the glycine-derived M-GLY extinguished the flame in horizontal flame spread tests at 4% by weight add-on. This paper reports on an extensive study aimed at understanding the molecular-level transformations of M-GLY-treated cotton upon heating in air at 300 °C, 350 °C and 420 °C. Thermogravimetric analysis (TGA) identified different thermal-oxidative decomposition stages and, coupled to Fourier transform infrared spectroscopy, allowed the volatile species released upon heating to be determined, revealing differences in the decomposition pattern of treated and untreated cotton. XPS analysis of the char residues of M-GLY-treated cotton revealed the formation of aromatic nanographitic char at lower temperature with respect to untreated cotton. Raman spectroscopy of the char residues provided indications on the degree of graphitization of treated and untreated cotton at the three reference temperatures. Solid state 13C nuclear magnetic resonance spectroscopy (NMR) provided information on the char structure as a function of the treatment temperature, clearly indicating that M-GLY favors the carbonization of cotton with the formation of more highly condensed aromatic structures.

Swelling studies on poly(n, n-dimethyl acrylamide-co-acrylic acid) hydrogels

Hydrogel copolymers based on N, N-dimethyl acrylamide (DMA) and acrylic acid (АAc) were synthesized with different molar composition ratios ([DMA-AAc] = 30÷70, 50÷50 and 70÷30) using ammonium peroxydisulfate as a free radical initiation system and in the presence of various amounts of N, N’-methylene bis (acrylamide) as a crosslinker agent (0.05, 0.1 and 0.3 mol. %) and water as reactant medium. The swelling technique characterized the obtained copolymer by different amounts to added of the crosslinking agent. While a large amount of crosslinking agent in the poly (DMA-co-AAc) hydrogels was reduced the swelling degree in the water medium, a smaller amount in the gel indicated the tendency of the gel to burst. Absorption studies were made using on different concentrations of copper sulphate (CuSO4). Poly (DMA-co-AAc) hydrogels absorption capacity is competitive when there is more N, N-dimethyl acrylamide content in copolymer than others. The swelling ratios of low concentration of Cu (II) ion are higher than those of higher concentration of Cu (II) ion. Hydrogel gave the highest swelling ratio for the solution containing the lowest Cu (II) ion concentration than for the solution containing the highest Cu (II) ion.

β-cyclodextrin modification by cross-linking polymerization as highly porous nanomatrices for olanzapine solubility improvement; synthesis, characterization and bio-compatibility evaluation

Herein, we report highly porous and amorphous nanomatrices developed by cross-linking polymerization with subsequent condensation technique for solubility, dissolution and ultimately bioavailability enhancement of poorly soluble drug olanzapine (OLN). β-cyclodextrin was chemically cross-linked with monomer 2-acrylamido 2-methylpropane sulfonic acid (AMPS) by using methylene bis acrylamide (MBA) as cross-linking agent. Developed nanomatrices were characterized by zetasizer, FTIR, XRD, SEM, DSC, swelling, sol-gel, drug loading, stability, porosity (%), solubility, and in-vitro dissolution analysis. The developed porous nanomatrices are intended for oral administration of poorly soluble drugs therefore, to determine the biocompatibility of the system to the biological environment, in-vivo cytotoxicity study was also conducted using rabbit model which endorsed the safety of the nanomatrices with biological system. The particle size of nanomatrices were found 152.30 ± 07.46 d.nm. XRD analysis depicted the highly amorphous nature of nanomatrices while. To evaluate the pharmacokinetic profile of olanzapine, in-vivo studies were also conducted. The in-vivo and dissolution experiments revealed that drug release characteristics were significantly improved by nanomatrices as compared with the reference product (OLANZIA®). The solubility of olanzapine by the developed nanomatrices was enhanced noticeably up to 40.11 times which is higher than previously reported β-cyclodextrin formulations. The efficient method of preparation, improved solubility, rapid and high dissolution and non-toxic βCD-co-poly (AMPS) nanomatrices may be a promising approach for oral delivery of poorly soluble drugs.

Synthesis of sulfonated melamine-functionalized Fe3O4@SiO2@Si–(CH2)3@melamine nanoparticles and its application in the synthesis of 4,4’-(aryl methylene)bis(3-methyl-1H-pyrazol-5-ol)s and hexahydroquinolines

Synthesis of sulfonated melamine-functionalized Fe3O4@SiO2@Si–(CH2)3@melamine nanoparticles and its application in the synthesis of 4,4’-(aryl methylene)bis(3-methyl-1H-pyrazol-5-ol)s and hexahydroquinolines

A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor

A convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural diversity of the synthesized compounds was demonstrated. In the electrophysiological experiments using the patch clamp technique on Purkinje neurons, the compound 1,4-phenylenedi(methylene)bis(5-aminoisoxazole-3-carboxylate) was shown to be highly potent positive modulator of the AMPA receptor, potentiating kainate-induced currents up to 70% at 10−11 M.

Synthesis of pyrazolone based heterocylic bisazo acid dyes and their dyeing performance on silk and wool fibers

In the present work, the aim is to show the utilization of heterocyclic bisazo acid dyes (3a-3 h) based on 1-phenyl-3-methyl-5-pyrazolone, which was synthesized by coupling of tetrazotised 3,3′-methylene bis (2-amino-5-iodo benzoic acid) with various pyrazolone coupling components (a-h). Dyes synthesised by elemental nitrogen analysis, IR and 1HNMR spectra were characterised. They were tested on wool and silk. The result showed good to excellent rubbing fastness and wash fastness properties as well fair to very good light fastness. Also, the absorption spectra and colorimetric data (L*, a*, b*, C*, H*, K/S) was analysed.

Nonlinear optical behavior of non‐centrosymmetric biferrocenyl Schiff‐base derivatives and their DNA binding potential supported by DFT and electrochemical investigations

AbstractTwo new non‐centrosymmetric biferrocenyl Schiff bases, that is, N‐(ferrocenylmethylene)‐4‐(4‐(ferrocenylmethyleneamino)phenoxy)benzenamine (FeL1) and 4,4′‐([1,1′‐biferrocenyl]‐4,4′‐diylbis(methylene)bis(N‐benzylideneaniline) (FeL2), have been synthesized and studied by density functional theory (DFT) to understand their nonlinear optical (NLO) behavior. The synthesized compounds were characterized by FTIR, NMR, and UV–visible spectroscopic techniques. DFT studies were performed to obtain the polarizability and first‐order hyperpolarizability parameters useful in determining the NLO response. Results indicate that the substituted biferrocenyl Schiff bases show a substantial increase in first‐order hyperpolarizability (44 times greater than the reference urea) compared with unsubstituted ferrocene. The enhanced NLO behavior follows the trend FeL2 > FeL1 > urea. Bader's atoms in molecules (AIM) theory has been employed to obtain topological parameters and critical points to evaluate the nature and strength of different types of intramolecular interactions. Charge delocalization in the complexes was investigated through natural bond order (NBO) analysis. It was observed that intramolecular charge transfer (ICT) is responsible for the optical nonlinearity of the biferrocenyl Schiff bases, with hydrogen bonding playing a prominent role in the bonding networks leading to increased hyperpolarizability. Furthermore, molecular electrostatic potential (MEP) surfaces of the molecular systems have also been analyzed. From an application viewpoint, the interaction of the biferrocenyl derivatives with fish‐sperm DNA was studied through spectrophotometric and electrochemical measurements. Results indicate major groove binding with DNA, which is also predicted by molecular docking studies.

Crystallographic and Spectroscopic Investigations on Oxidative Coordination in the Heteroleptic Mononuclear Complex of Cerium and Benzoxazine Dimer.

Among lanthanide-based compounds, cerium compounds exhibit a significant role in a variety of research fields due to their distinct tetravalency, high economic feasibility, and high stability of Ce(IV) complexes. Herein, a systematic investigation of crystallographic information, chemical properties, and mechanistic formation of the novel Ce(IV) complex synthesized from cerium(III) nitrate hexahydrate and 2,2′-(methylazanediyl)bis(methylene)bis(4-methylphenol) (MMD) ligand has been explored. According to the analysis of the crystallographic information, the obtained complex crystal consists of the Ce(IV) center coordinated with two nitrate ligands and two bidentate coordinated (N-protonated and O,O-deprotonated) MMD ligands. The fingerprint plots and the Hirshfeld surface analyses suggest that the C–H⋯O and C–H⋯π interactions significantly contribute to the crystal packing. The C–H⋯O and C–H⋯π contacts link the molecules into infinite molecular chains propagating along the [100] and [010] directions. Synchrotron powder X-ray diffraction (XRD) and X-ray absorption spectroscopy (XAS) techniques have been employed to gain an understanding of the oxidative complexation of Ce(IV)-MMD complex in detail. This finding would provide the possibility to systematically control the synthetic parameters and wisely design the precursor components in order to achieve the desired properties of novel materials for specific applications.

Influences of Chemical Functionalities on Crystal Structures and Electrochemical Properties of Dihydro-benzoxazine Dimer Derivatives

Dihydro-1,3,2H-benzoxazine dimer derivatives or dihydro-benzoxazine dimers are a class of compounds typically prepared by ring-opening reactions between dihydro-benzoxazines and phenols. Dihydro-benzoxazine dimers act as chelating agents for several transition and rare-earth cations. To better understand the chelating properties, it is necessary to examine their structural features and electrochemical characteristics thoroughly. However, the electrochemical properties of dihydro-benzoxazine dimers have not been tremendously examined. Herein, eight derivatives of dihydro-benzoxazine dimers possessing different substituents on the benzene ring and the tertiary-amine nitrogen were synthesized as model compounds to investigate their influences on crystal structures and electrochemical properties. The crystal structure of the dihydro-benzoxazine dimer, namely 2,2′-(cyclohexylazanediyl)bis(methylene)bis(4-methoxyphenol) (7), is identified for the first time and further used to compare with the crystal structures of other derivatives reported previously. For all the derivatives, intermolecular O–H⋅⋅⋅O hydrogen bonds are the significant interactions to hold the crystal packing of (7) and also the other derivatives. Hirshfeld surface analyses confirm the presence of intermolecular O–H⋅⋅⋅O hydrogen bonds. Redox behavior of the eight dihydro-benzoxazine dimers was studied by cyclic voltammetry. An oxidation peak observed at 0.25–0.47 V corresponds to the oxidation of the phenolic –OH group to the phenoxonium intermediate. The shift in the electrochemical peak positions is due to the different abilities of the substituents to stabilize the phenoxonium cation intermediate. The stabilizing power is ranged in the following order: methoxy > dimethyl > ethyl ≈ methyl, and N-cyclohexyl > N-methyl. Thus, the derivative (7), which contains both the methoxy and N-cyclohexyl groups, has the lowest oxidation potential. Our work elucidates the effect of the substituents on the crystal structures and electrochemical properties of the dihydro-benzoxazine dimers.

Application ofPoly (Agar-Co-Glycerol-Co-Sweet Almond Oil) Based Organo-Hydrogelsas a Drug Delivery Material.

In this study, it was aimed to investigate the synthesis, characterization and drug release behaviors of organo-hydrogels containing pH-sensitive Agar (A), Glycerol (G), Sweet Almond oil (Wu et al. in J Mol Struct 882:107–115, 2008). Organo-hydrogels, which contained Agar, Glycerol and different amounts of Sweet Almond oil, were synthesized via the free-radical polymerization reaction with emulsion technique using glutaraldehyde or methylene bis acrylamide crosslinkers. Then, the degree of swelling, bond structures, blood compatibility and antioxidant properties of the synthesized organo-hydrogels were examined. In addition, Organo-hydrogels which loaded with Ceftriaxone and Oxaliplatin were synthesized with the same polymerization reaction and release kinetics were investigated. In vitro release studies were performed at media similar pH to gastric fluid (pH 2.0), skin surface (pH 5.5), blood fluid (pH 7.4) and intestinal fluid (pH 8.0), at 37 °C. The effects on release of crosslinker type and sweet almond oil amount were investigated. Kinetic parameters were determined using release results and these results were applied to zero and first-order equations and Korsmeyer-Peppas and Higuchi equations. Diffusion exponential was calculated for drug diffusion of organo-hydrogels and values consistent with release results were found.

Radiation initiated synthesis, characterization, and swelling behavior of poly (acrylic acid‐co‐acrylamide)/starch grafted hydrogel

AbstractThe powerful waves of ultrasound are used in polymerization reactions in the absence of initiator. In the present research, the hydrogel was obtained by water‐soluble acrylic monomers, starch, and the crosslinking agent of methylene bis acrylamide dissolved in water/glycerol dual. The hydrogel is formed by these waves only in viscous environments such as glycerol, heat, or initiator is not required. In the presence of ultrasound, the time of product formation is reduced to a few minutes. Moreover, the resulting hydrogels have more uniform microscopic structure and are more swollen. The structure of the grafted hydrogel was examined meanwhile the hydrogel swelling in three environments of pure water, saltwater, and under pressure was measured. It was found that the grafted hydrogel has double swelling rate in the pure. Also, after loading the ciprofloxacin into the synthesized hydrogel, this drug is released 99% in initial 20 min. 0.1 g starch in 1.5 g acrylic hydrogel has the most drug release. The high swelling capacity in the pH ranges of 5–9 shows the extension of drug application in acidic or alkaline environments, and also after several using the gel and the capacity of water absorbency, which was about 70% of its initial water, indicates the perfect reusability capacity of the gel.

Removal of heavy metals from abandoned smelter contaminated soil with poly-phosphonic acid: Two-objective optimization based on washing efficiency and risk assessment

Soil washing is a feasible technology to achieve rapid remediation and reuse of contaminated sites. However, there is still a need to seek eco-friendly and low-cost washing reagents. In this study, a two-objective optimization method has been proposed to investigate the removal efficiencies of eluents and risk of migration (risk assessment code, RAC) of residual metal simultaneously when soil Cd and Pb washed by polyamino polyether methylene phosphonate (PPMP) and bis (hexamethylene triamine penta (methylenephosphonic acid)) (BHMT). The coefficients of determination of the equations proved that D-optimal mixture design could be used for optimizing and modeling of the two objectives during soil washing. And their single-factor (concentration, solution pH, or contact time) and interaction effects indicated that PPMP react with Cd and Pb through chelation at strong acid in soil, whereas acid dissolution effect would convert the stable form of soil Pb into unstable form. BHMT could rapidly remove more acid-soluble fractions of Cd and Pb through the electric double layer adsorption, and is favorable under neutral conditions. Moreover, the optimum removal efficiencies of soil Cd and Pb were 83.98 and 41.29%, and RACs were 45.1 and 5.16% respectively in PPMP washing; accordingly, 69.31 and 28.11% of optimum removals and 32.45 and 0.98% of RACs for soil Cd and Pb were obtained in BHMT leaching. Therefore, PPMP and BHMT are two feasible remediation reagents of the abandoned industrial soils contaminated by heavy metals.

Synergistic effect of potassium iodide on corrosion inhibition of copper by tetraphosphonic acid in hydrochloric acid solution

Synergistic effect of KI on the corrosion inhibition efficiency of methylene bis [(2-hydroxy-5, 1-phenylene) bismethylene] tetraphosphonic acid (TPA) on corrosion of copper in 0.5 M HCl have been tested using weight loss, electrochemical impedance spectroscopy (EIS) and potentiodynamic polarization techniques. The study show that copper is more efficiently inhibited by decreasing the concentration of TPA, and enhancement in inhibition efficiency was observed with an addition of 0.02 M potassium iodide due to synergism. The highest inhibition efficiency of 91% was observed for10−8 M TPA while an addition of 0.02 M KI to 10−8 M TPA improved the inhibition efficiency to 98%. Electrochemical test data prove that they are cathodic inhibitor and exhibit remarkable corrosion inhibition ability. The morphology confirms that the synergistic effect is due to coadsorption of iodide ions and TPA is co-operative in nature. Furthermore, the inhibition efficiency of (TPA + KI) does not depend on temperature. The adsorption of TPA alone or with iodide ions on the metal surface followed Frumkin adsorption isotherm. Thermodynamic parameters (K ads, ΔG°ads, ΔS°ads) were calculated using the adsorption isotherms from temperatures ranging from 25 to 55 °C. The experimental results were confirmed by density functional theory (DFT) and molecular dynamic simulation (MDS) calculation.

Sulfonated poly (Ester-Urethane) / ionic liquids systems: synthesis, characterization and properties

A new class of materials based on crosslinked poly (ester-urethane) containing low proportions of ionic liquid were synthesized using biobased sulfonated oligoester diol, trimethylol propane (TMP), 4,4′-methylene bis(cyclohexyleisocyanate) (HMDI) and 1-butyle-3-methylimidazolium acetate (BMIMAc). Sulfonated oligoester with a well-controlled molar mass was first obtained by melt polycondensation catalyzed by Ti(OBu)4. The resulting products were characterized by, 1HNMR, DSC and MALDI-TOF MS techniques. The systems of crosslinked poly (ester-urethane) and ionic liquid were obtained via a one-shot process. FTIR technical was used for a more effective control of crosslinking reaction. The Thermomechanical analysis of the resulting materials were performed by DSC and DMA technique. Furthermore, the hydrolytic and oxidative degradation study revealed that the degradation of systems mainly depends on the content in ionic liquid and the crosslinking degree of networks.

Synthesis of amides and esters containing furan rings under microwave-assisted conditions

Abstract In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO− or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl)furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5-dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furandicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.