Aliphatic Anhydrides Research Articles

Design, Synthesis, Characterization, Docking and Biological Assessment of Innovative 5-(Pyrazin-2-yl)-1, 3, 4-oxadiazol-2-amine Derivatives for Enhanced Anti-fungal and Anti-Bacterial Activities

This study presents a new class of compounds, specifically 5-(Pyrazine-2-yl) 1,3,4-oxadiazol-2-amine and its derivatives, synthesized with aliphatic anhydrides. The successful synthesis is validated through comprehensive characterization involving 1H-NMR, 13C-NMR, FTIR, and Mass Spectra. The synthesized subordinates, represented as formula 3 and 3(a-h), go through orderly assessment for in-vitro antibacterial and antifungal properties against Staphylococcus aureus, Escherichia coli, and Candida albicans. The assessment of antimicrobial activity, conducted through the disc diffusion method with reference compounds, reveals significant efficacy in a majority of the synthesized compounds, with some exhibiting particularly promising results. Molecular docking studies further highlight favourable interactions for all novel compounds. This examination underlines the capability of 5-(Pyrazine-2-yl) 1,3,4-oxadiazol-2-amine subsidiaries against both bacterial and fungal strains.

Study on the Reactivity of Mixed Carboxylic Palmitic Anhydrides via the Esterification Reaction Using Heterogeneous Catalyst

Abstract: of Organic Chemistry LR17ES08: Faculty of Sciences in Sfax, Route de Soukra Km 3,5 – BP 1171-3000, Sfax, Tunisia : The anhydrides were prepared in the presence of triethylamine in the organic solvent by a reaction between fatty acid and acid chloride. Mixed aromatic palmitic were more reactive and selective than the aliphatic anhydrides. The palmitic group was the most involved in acylation. Good yields of fatty esters were obtained with total conversion of mixed anhydrides.

Catalytic Ketonization over Oxide Catalysts (Part XIV): The Ketonization and Cross-Ketonization of Anhydrides, Substituted Acids and Esters

A series of 20 wt.% MO2/S catalysts (where M = Ce, Mn or Zr and S = SiO2 or Al2O3) were prepared using various precursors of the active phases. The resulting catalysts were characterized using different methods (XRD, TPR and SBET). For the first time, anhydrides were used as potential starting materials for ketone synthesis. This novel reaction was performed on various aliphatic anhydrides in the presence of catalysts within a temperature range of 523–723 K. For all anhydrides, except for pivalic anhydride, the appropriate ketones were obtained with good or very good yields. The vapor-phase catalytic ketonization of esters of benzene-1,x-dicarboxylic acids (x = 2, 3 or 4) with acetic acid were studied in the range of 673–723 K in order to obtain 1,x-diacetylbenzenes. Their yields strongly increased with an increase in the x value (0, 8 and 43% for x = 2, 3 and 4, respectively). The presence of acetophenone as a side product was always noted. In the case of ω-phenylalkanoic acids, their vapor-phase ketonization with acetic acid led to the formation of appropriate ketones with 47–49% yields. Much lower yields of ketones (3–19%) were obtained for acids and ethyl esters containing heterocycle substituents (with O or S atoms) and/or vinyl groups. In the reaction between ethyl 4-nitrophenylacetate and acetic acid, only the products of ester decomposition (p-toluidine and p-nitrotoluene) were determined.

Light-Mediated Synthesis of Aliphatic Anhydrides by Cu-Catalyzed Carbonylation of Alkyl Halides

Acid anhydrides are valuable in the chemical industry for their role in synthesizing polymers, pharmaceuticals, and other commodities, but their syntheses often involve multiple steps with precious metal catalysts. The simplest anhydride, acetic anhydride, is currently produced by two Rh-catalyzed carbonylation reactions on a bulk scale for its use in synthesizing products ranging from aspirin to cellulose acetate. Here, we report a light-mediated, Cu-catalyzed process for producing aliphatic, symmetric acid anhydrides directly by carbonylation of alkyl (pseudo)halides in a single step without any precious metal additives. The transformation requires only simple Cu salts and abundant bases to generate a heterogeneous Cu0 photocatalyst in situ, maintains high efficiency and selectivity upon scale-up, and operates by a radical mechanism with several beneficial features. This discovery will enable the engineering of bulk processes for producing commodity anhydrides efficiently and sustainably.

A New Unsaturated Aliphatic Anhydride from Aspergillus candidus T1219W1, an Endophytic Fungus, from Pittosporum mannii Hook f.

A new unsaturated aliphatic anhydride derivative (Z)-(12Z)-heptadec-12-enoic-2′-hydroxypropanoic anhydride (1) and ten known compounds, three flavonoids (2–4), two terphenyllins (5-6), four triterpenoids (7-8, 10-11), and one n-fatty acid (9), were isolated from the EtOAc extract of Aspergillus candidus T1219W1, an endophytic fungus, inhabiting Pittosporum mannii. All the isolated compounds were characterized using 1D- and 2D-NMR and HR-EI experiments together with the reported literature. p-terphenyls are suggested to be the chemophenetic marker of the genus Aspergillus. The ethyl acetate crude extract as well as some isolated compounds of A. candidus was assayed for antibiofilm activity, anti-inflammatory (ROS) activity, and cytotoxicity on brine shrimps and the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) cytotoxicity assay on 3T3 cell lines. The tested sample showed good antibiofilm activity with the lowest MBEC50 obtained at 64 μg/mL. Compounds showed low anti-inflammatory activity even at high concentration (250 μg·mL−1 with an IC50 of 59.6 ± 0.1 μg·mL−1) with moderate cytotoxicity on brine shrimps at high concentration (1000 μg·mL−1, with 46.67% mortality). However, no cytotoxic activity was observed against 3T3 cell lines.

Acylation of Peat by Aliphatic Anhydrides

Acylation of Peat by Aliphatic Anhydrides

Palladium-Catalyzed One-Step Synthesis of Stereodefined Difunctionalized Glycals

Palladium-Catalyzed One-Step Synthesis of Stereodefined Difunctionalized Glycals

Bay-Region Annulative π-Extension of o-Iodobiphenyls with Aliphatic Anhydrides Catalyzed by Pd(OAc)2.

Bay-region annulative π-extension of o-iodobiphenyls with aliphatic anhydrides was developed. Many o-iodobiphenyls and aliphatic anhydrides can react well under the optimized conditions. A lot of phenanthrol derivatives can be efficiently prepared by this approach. The control experiments support that dibenzopalladacyclopentadienes may be the reaction intermediates.

The synthesis of derivatives of tetra(hexa)hydro[1,2,3]triazolo-[4,5-e][1,4]diazepines and their acylation

Aim. To study the conditions for reduction of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines and develop the method for the synthesis of their tetra- and hexahydroderivatives.Results and discussion. It has been found that the functional hydroxy and carbonyl groups of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines tend to selective reduction with complex metal hydrides, and it has allowed to develop methods for the synthesis of their hydrogenated derivatives and to carry out the acylation of the diazepine cycle.Experimental part. The selective reduction of the hydroxy group was obtained by the interaction of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines with a 2-fold excess of NaBH4 in the boiling isopropanol. It allowed obtaining derivatives of tetrahydro[1,2,3]triazolo[4,5-e][1,4]diazepine-8(3H)-one with the yield of 61-82 %. The complete reduction of the diazepine cycle can be achieved only by using a 5-fold excess of LiAlH4-Me3SiCl hydration system and long-term boiling in THF. It has been shown that the tetrahydroderivatives synthesized with aliphatic carboxylic anhydrides are prone to selective acylation of the N4 diazepine ring atom, while hexahydroderivatives form a product of acetylation at N4 and N6 atoms.Conclusions. The conditions for the partial and complete reduction of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines have been found, convenient methods for the synthesis of tetrahydro- and hexahydroderivatives have been developed, and their directed functionalization by acyl groups has been performed.

Synthesis, Spectroscopic Properties and DFT Calculation of Novel Pyrrolo[1′,5′-a]-1,8-naphthyridine Derivatives through a Facile One-pot Process

Novel pyrrolo[1′,5′-a]-1,8-naphthyridine compounds (L1-L4) have been synthesized through a facile one-pot process by the reaction of the corresponding 1,8-naphthyridines with aliphatic anhydride. The structures were established by spectroscopic data. Further, X-ray crystal analysis of 7-diacetamino-2,4-dimethy-1,8-naphthyridine (L1) identifies its molecular structure and reveals π- π stacking. The synthetic mechanisms for L2, L3 were studied by density functional theory calculations. And a comprehensive study of spectroscopic properties involving experimental data and theoretical studies is presented. L1 exhibited electronic absorption spectrum with λ max at ∼320 nm. L2-L4 exhibited similar electronic absorption spectra with λ max at ∼390 nm that is tentatively assigned to π→π* transition. The assignment was further supported by density functional theory (DFT) calculations. Novel pyrrolo[1′,5′-a]-1,8-naphthyridine compounds have been synthesized through a facile one-pot process. Further, X-ray crystal analysis and spectroscopic properties are presented.

UV-Assisted 3D Printing of Glass and Carbon Fiber-Reinforced Dual-Cure Polymer Composites.

Glass (GFR) and carbon fiber-reinforced (CFR) dual-cure polymer composites fabricated by UV-assisted three-dimensional (UV-3D) printing are presented. The resin material combines an acrylic-based photocurable resin with a low temperature (140 °C) thermally-curable resin system based on bisphenol A diglycidyl ether as base component, an aliphatic anhydride (hexahydro-4-methylphthalic anhydride) as hardener and (2,4,6,-tris(dimethylaminomethyl)phenol) as catalyst. A thorough rheological characterization of these formulations allowed us to define their 3D printability window. UV-3D printed macrostructures were successfully demonstrated, giving a clear indication of their potential use in real-life structural applications. Differential scanning calorimetry and dynamic mechanical analysis highlighted the good thermal stability and mechanical properties of the printed parts. In addition, uniaxial tensile tests were used to assess the fiber reinforcing effect on the UV-3D printed objects. Finally, an initial study was conducted on the use of a sizing treatment on carbon fibers to improve the fiber/matrix interfacial adhesion, giving preliminary indications on the potential of this approach to improve the mechanical properties of the 3D printed CFR components.

Thermal and dielectric properties of newly developed linear aliphatic-ether linked bismaleimide-polyhedral oligomeric silsesquioxane (POSS-AEBMI) nanocomposites

A new series of four different linear aliphatic ether linked aromatic bismaleimides (AEBMIs) were synthesized from the respective linear aliphatic ether-linked aromatic diamines and maleic anhydride. Further, the POSS-AEBMI nanocomposites were developed by Michael addition reaction of bismaleimide with varying mass percentages of octa(aminophenyl)silsesquioxane and were characterized by the fourier transform infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis. Data from thermal studies revealed that the POSS-reinforced AEBMI nanocomposites possesses higher glass transition temperature (Tg), thermal stability, limiting oxygen index, and lower dielectric constant when compare to that of neat AEBMI. X-ray diffraction and transmission electron microscopy analysis confirmed the molecular level dispersion of POSS in the AEBMI matrix.

Catalyst-Free, Direct, High Regio- and Chemoselective Conversion of Epoxides to Vicinal Haloesters Under Mild, Neutral, and Solvent-Free Conditions

A catalyst-free, high regio- and chemoselective method is described for the mild conversion of wide varieties of epoxides directly to their corresponding vicinal haloesters using quaternary ammonium halides R4N+X- (X equals; Cl, Br, I; R = n-butyl, n-pentyl, n-hexyl) in the presence of an aliphatic or aromatic carboxylic anhydride at room temperature under neutral and solvent-free conditions.

Synthesis and Properties of Sodium Mono-alkylamide Maleate Surfactants

Abstract The synthesis of a series of sodium mono-alkylamide maleate surfactants was described, and the surface activity properties of the surfactants were studied. The mono-alkylamide maleic acids were synthesized by amidation using primary aliphatic amine (lauryl, myristyl, cetyl) and maleic anhydride as starting material. They were structurally characterized by IR, 1H-NMR and MS. The sodium mono-alkylamide maleate surfactants were prepared by neutralization of the precursor mono-alkylamide maleic acids with sodium hydroxide. They reduced the surface tension of water to 32–34 mN · m–1 at concentration levels of 10–4–10–3 mol · L–1.

Preparation and antimicrobial activity of poly (vinyl chloride)/gelatin/montmorillonite biocomposite films

The aim of this study was using a novel antimicrobial thermoplastic plasticizer based on aliphatic anhydride derivative dodecenyl succinic anhydride (DSA) for blending poly (vinyl chloride), PVC, with gelatin in presence of montmorillonite (MMT) using Brabender via polymer melting technique. This anhydride-based plasticizer blended the membrane ingredients homogenously under melting process. The used plasticizer exhibited high performance antimicrobial potency for some biomedical and industrial applications. The prepared biocomposite films were evaluated for antimicrobial activity using agar disc diffusion method against gram-positive and gram-negative bacteria such as: Staphylococcus aureus (S. aureus), Klebsiella pneumonia (K. pneumonia), Bacillus cereus (B. cereus), Bacillus subtilis (B. subtilis) and Escherichia coli (E. coli). The majority of these biocomposites, except the plasticized PVC with DOP, have shown inhibitory effect at different concentrations (1.0-20) mg/ml against all above mentioned bacteria. However, C. albicans and A. niger were the most resistant strains.

Catalyst-free, direct, high regio-, and chemo-selective conversion of epoxides to 2-thiocyanatoalkyl alkanoates under neutral and solvent-free conditions

A catalyst-free, direct, high regio-, and chemo-selective method is reported for the facile conversion of a wide variety of epoxides to their corresponding 2-thiocyanatoalkyl alkanoates, which contain two important functional groups (ester and thiocyanate), using a mixture of tetrabutylammonium rhodanide ((n-Bu)4NSCN) and an aliphatic or aromatic carboxylic anhydride under neutral and solvent-free conditions.

Expedient Synthesis, on Large Scale, of Aliphatic Chaetomellic Anhydrides from N-Allyl-2,2-dichlorocarboxyamides

Chaetomellic anhydride A and an analog (with two additional carbons) were obtained, on a preparative scale, starting from amides derived from the acylation of 2-(2-propenylamino)pyridine with 2,2-dichloropalmitic or 2,2-dichlorostearic acid. An alternative approach, in which the methyl substituent of the target anhydride is introduced by the carboxylic acid reactant and the long aliphatic chain is added through the allylamino moiety, proved unviable.

Synthesis of Novel Pyrrolo[1′,5′‐a]‐1,8‐naphthyridine Derivatives through a Facile One‐Pot Process

Novel pyrrolo[1′,5′‐a]‐1,8‐naphthyridine compounds have been synthesized through a facile one‐pot process by the reaction of the corresponding 1,8‐naphthyridines with aliphatic anhydride. The structures were established by spectroscopic data. Further X‐ray crystal analysis of 4′‐acetyl‐7‐methyl‐pyrrolo[1′,5′‐a]‐1,8‐naphthyridine (1) identifies its intriguing molecular structure and reveals the strong π‐π stacking.

Synthesis, characterization, and properties of novel polyetherester polyols and developed polyurethanes

AbstractThree kinds of cyclic anhydrides, which stand for aliphatic anhydride, aromatic anhydride, and anhydride containing double bond: succinic anhydride, phthalic anhydride, and maleic anhydride have been copolymerized with propylene oxide and low molecular weight polyoxypropylenediol via ring‐opening copolymerization initiator by double metal cyanide complex catalyst to synthesis a series of polyetherester (PEE) polyols. The structure of the obtained copolymers was confirmed by several analysis methods. Three kinds of polyetherester polyurethane (PEEPU) were thus synthesized by polymerization of as‐synthesized PEE polyol with 4,4′‐diphenylmethane diisocyanate. The mechanical properties of the obtained PEEPU were tested. The results showed that the mechanical properties of three polyurethanes are different based on their structure and composition. The inducing of the rigid phenyl group in the soft segment can improve the mechanical strength remarkably. The influences of ester content in soft segment and the hard segment content on the mechanical properties of PEEPU were studied. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 417–424, 2007

1,1'-(Ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) as a recyclable catalyst for acylation

Ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) catalyzes the acylation of structurally diverse alcohols, amines, thiols, and phenols with a variety of aliphatic and aromatic anhydrides. Steric factors in substrates as well as anhydrides and solvent play significant role during the formation of acylates. Chemoselective mono acetylation of symmetrical diols, primary hydroxy group over secondary and phenolic group and amines over phenols has been achieved. The compatibility of the protocol has been shown by the survival of different acid sensitive functionalities under the present reaction condition. The solvent, acetone, reacts with EDPBT giving bromoacetone and HBr, thus suppressing the bromination of substrates otherwise amenable to bromination. The reagent EDPBT being devoid of phase transfer property and owing to the high solubility of its precursor 1,1'-(ethane-1,2-diyl)dipyridinium dibromide (EDPDB) in water, it was possible to isolate pure acylates by an aqueous work-up circumventing the need for further purification. The process is superior owing to the recyclability of the reagent. The spent reagent can be recovered, regenerated, and reused without any significant loss.