Reaction Of Anhydride Research Articles

Removal of lead (II) ions from water using chitosan/polyester crosslinked spheres derived from chitosan and glycerol-based polyester

The present study reports development of eco-friendly polymeric spheres derived from crosslinking of chitosan (CTS) with different polyesters. The polyesters were synthesized via polycondensation reaction of maleic anhydride with 1,4-butadiol and glycerol, potential renewable chemical, as hydroxyl sources. The structures of the prepared polyesters and the crosslinking of CTS/polyester spheres were confirmed by Fourier transform infrared spectroscopy. Crosslinking of CTS with polyesters enhances the structure and the stability of CTS-based spheres in aqueous media, but decreases its hydrophilicity. The obtained spheres were employed for adsorption of lead ions (Pb2+) from aqueous solutions. The batch adsorption experiments were evaluated to investigate the effect of glycerol-loading on adsorption of Pb2+ ions. The results indicated that the amount of adsorbed (Pb2+) ions was increased with time and operating temperature. The maximum 83.5% removal efficiency of Pb2+ ions from aqueous solution was achieved at pH= 5.0. The experimental data was described with the Langmuir and Freundlich isotherm models, whereas the Freundlich model showed the best fit of the data.

Synthesis and in vitro anticancer activity evaluation of spiro[indolo[2,1-b]quinazoline-pyrano[2,3-c]pyrazole] via sequential four-component reaction

Cancer is still incurable and it is considered as a main health problem worldwide. The identification of novel compounds with high toxicity and low side effects is one of the biggest challenges among interested researchers. In this study, a rapid and simple strategy for synthesis of spiro[indolo[2,1-b]quinazoline-pyrano[2,3-c]pyrazole] derivatives via sequential four-component reaction of isatoic anhydride, isatin, malononitrile, and 3-methyl-pyrazolones in CH2Cl2 at room temperature is described. This procedure has short reaction time and mild reaction conditions. Simple purification and no chromatographic process, are the other notable advantages of this protocol which make it attractive. To evaluate the anticancer activity of our synthetic compounds, pancreatic cancer cell (Panc1), cancer cell of breast (MDA-MB-231), colon cancer cell (HT-29), and normal human adult dermal fibroblast (HDF) were firstly cultured and by using MTT assay, the possible toxicity of related compounds was analyzed. Our results suggested that no compounds have 50% growth inhibitory concentration (IC50) values lower than etoposide (as a reference drug) against all cancer cell lines and among nine synthetic compounds, only 4a compound was effective against Panc1 pancreatic cancer cells.

Microwave-assisted, catalyst and solvent free synthesis of tryptanthrin derivatives and their in-vitro cytotoxic activity on prostate DU145 cancer cell lines

A straightforward and efficient synthesis of tryptanthrin derivatives has been accomplished by the addition reaction of isatoic anhydrides and isatins under microwave irradiation. This decarboxylative and dehydrative addition reaction proceeded under solvent free conditions. In vitro cell based bioassay results revealed that 3ab and 3bb had unique cytotoxicity and selectivity with IC50 values of 5.90 ± 3.65 μM and 1.96 ± 0.83 μM, respectively in DU145 cells and they were found to be nontoxic to normal prostate epithelial RWPE-1 cells up to 25 μM.

Synthesis and evaluation of antioxidant and antimicrobial activity of new spiropyrrolopyrrolizine compounds: Using Fe3O4/TiO2/Multiwall carbon nanotubes (MWCNTs) magnetic nanocomposites

In this research, we synthesized the Fe3O4/TiO2/multiwall carbon nanotubes (MWCNTs) magnetic nanocomposites using water extract of Spinacia oleracea leaves, and the high performance of synthesized catalyst was confirmed by employing of it in the multicomponent reaction of reaction of isatoic anhydride, tert‐butylisocyanide, diamines, or hydroxyamines, electron‐deficient acetylenic ester, α‐haloketones, and Et3N in water at ambient temperature for the production of new spiropyrrolopyrrolizine compounds in high yields. This catalyst could be used several times in these reactions and have main role in the yield of product. The synthesized compounds have NH and OH group in their structure and, for this reason, have good antioxidant activity. Also, employing Gram‐positive and Gram‐negative bacteria in the disk diffusion procedure confirmed the some spiropyrrolopyrrolizine derivatives antimicrobial effect. The results showed that synthesized compounds prevented the bacterial growth. This used procedure for preparation of spiropyrrolopyrrolizine derivatives have some advantages such as low reaction time, product with high yields, and simple separation of catalyst and products.

Microwave assested synthesis of phthalimide amino derivatives with their antioxidant potential

Imide is the configuration of amide in which the nitrogen atom is affix to two carbonyl group. Imide mention to any compound which carry the divalent radical. Phthalimide possess a structural feature CHNO and an imide ring which help them to be biologically active and pharmaceutically useful.Phthalimides have served as starting materials and intermediates for the synthesis of many types of alkaloids and pharmacophores.In view of broad biological activity of phthalimide, we herein plan to synthesize a series of new phthalimide derivatives by incorporating new pharmacophores at various positions with the hope to get therapeutically active compounds. The aim the study is to synthesize phthalimide derivatives by using microwave assisted synthesis method and compare the activity of the synthesized molecules. Thus, the current communication employed the technology gracefully for the synthesis, identification and characterization of some novel derivatives by the reaction of Phthalic anhydride with urea, glycine, aniline, sulphanilic acid to yield various Phthalimide derivatives using domestic microwave by getting percentage yield 70.7%, 76.65%, 80.21% and 73.78% of synthesized compound BBBand Brespectively. The compound B(92.86%) showed higher percentage practical yield. All synthesized compound(s) were subjected to melting point determination, TLC analysis, column chromatography (for purification), H-NMR and Mass Spectrometry. All synthesized derivatives were subjected for DDPH scavenging activity, in which compound Bwas found to have high anti-oxidant potential (69.56%) when ascorbic acid was taken as standard. All the chemicals used were of highly pure and procured from Central Drug House (New Delhi).

Fabrication of a dual stimuli-responsive magnetic nanohydrogel for delivery of anticancer drugs

A dual stimuli-responsive magnetic nanohydrogel was fabricated as a potent drug delivery system (DDS) for ‘smart’ treatment of cancer by chemo/hyperthermia approach. For this objective, Fe3O4 nanoparticles (NPs) were produced via a co-precipitation approach and then modified by 3-(trimethoxysilyl) propylmethacrylate (MPS) moiety. The modified NPs were copolymerized with N,N′-(dimethylamino)ethyl methacrylate (DMAEMA), and maleic anhydride (MA) monomers by a free radical polymerization approach to afford a Fe3O4@P(DMAEMA-co-MA) core-shell NPs. Afterward, the NPs were shell crosslinked by the reaction of anhydride unites with neutralized cystamine (Cys). The fabricated pH- and reduction-responsive magnetic nanohydrogel was physically loaded with methotrexate (MTX), as an anticancer drug, and its drug loading efficiency (LE) was calculated as 64 ± 2.7%. The developed nanohydrogel/MTX exhibited proper stimuli-triggered drug release behavior that qualified it as an efficient DDS according to the abnormal micro-environment of cancerous tumors. The anticancer activity investigation using chemo/hyperthermia therapy approach by MTT-assay revealed that the nanohydrogel/MTX might show better clinical outcomes than those of the free MTX.

Developing “Polymer‐in‐Salt” High Voltage Electrolyte Based on Composite Lithium Salts for Solid‐State Li Metal Batteries

AbstractThe stringent demands for lithium salts make the design of “polymer‐in‐salt” type solid electrolyte restricted since it was proposed in 1993. Herein, a novel polymer‐in‐salt solid electrolyte is developed via a supramolecular strategy based on poly(methyl vinyl ether‐alt‐maleic anhydride) (PME) and novel single‐ion lithiated polyvinyl formal (LiPVFM)/lithium bis(trifluoromethylsulfonyl)imide (LiTFSI) composite salts (Dual‐Li). Hydroxyl of LiPVFM in Dual‐Li forms a strong hydrogen bond with the carboxylic acid group generated by the partial ring‐opening reaction of maleic anhydride in PME. Meanwhile, PME with abundant carbonyl enables the improved LiTFSI coordination in the polymer/salt composites. As a result, the greatly enhanced mutual solubility of PME and Dual‐Li is of importance to build a “polymer‐in‐salt” solid electrolyte (PISE), which exhibits high ionic conductivity of 3.57 × 10–4 S cm–1, wide electrochemical window beyond 5 V, and superior lithium‐ion transference number of 0.62 at 25 °C as well as excellent interfacial compatibility with electrodes. The as‐assembled LiCoO2||Li solid batteries present prominent high‐voltage cyclability with 89.2% capacity retention in 225 cycles. Furthermore, LiNi0.7Mn0.2Co0.1O2||Li pouch cells exhibit remarkable safety even under harsh conditions. The study offers a promising strategy to address the high voltage compatibility and interfacial issues using PISE in solid‐state batteries.

Production of Cyclic Anhydride-Modified Starches

Modified starches offer a biodegradable, readily available, and cost-effective alternative to petroleum-based products. The reaction of alkenylsuccinic anhydrides (ASAs), in particular, is an efficient method to produce amphiphilic starches with numerous applications in different areas. While ASAs are typically derived from petroleum sources, maleated soybean oil can also be used in an effort to produce materials from renewable sources. The reaction of gelatinized waxy maize starch with octenylsuccinic anhydride (OSA), dodecenylsuccinic anhydride (DDSA), a maleated fatty acid (TENAX 2010), phthalic anhydride (PA), 1,2,4-benzenetricarboxylic acid anhydride (trimellitic anhydride, TMA), and three maleated soybean oil samples, was investigated under different conditions. To minimize the reaction time and the amount of water required, the outcome of the esterification reaction was compared for starch dispersions in benchtop dispersed reactions, for starch melts in a heated torque rheometer, and for reactive extrusion in a pilot plant scale twin-screw extruder. The extent of reaction was quantified by 1H NMR analysis, and changes in molecular weight and diameter were monitored by gel permeation chromatography (GPC) analysis. The outcome of the reactions varied markedly in terms of reaction efficiency (RE), molecular weight distribution, and average hydrodynamic diameter, for the products derived from the different maleated reagents used, as well as for the different reaction protocols.

Synthesis and Study Antibacterial Activity of Some New Polymers Containing Maleimide Group

By condensation of benzaldehyde with thiourea in absolute ethanol in the presence of glacial acetic acid as a catalyst, the Schiff base(1-benzylidenethiourea)[I] was synthesized by synthesis of 4-(3-benzylidenethioureido)-4-thioxobut-2-enoic acid compound[II] by reaction of maleic anhydride with schiff base [I] in DMF. When treating compound [II] with ammonium persulfate (NH4)2S2O8 (APS) as an ethanol initiator to obtain polymer [III], compound [III] reacted to polymer [IV] with SOCl2 in benzene. Sulfamethizole, celecoxib, salbutamol, 4-aminoantipyrine to yield polymers [V-VIII], compound [IV] reaction with different drugs. Spectral evidence established the structure of synthesized compounds: FTIR and 1HNMR, UV-Vis Spectroscopy and Elemental Analysis (C.H.N-S). These synthesized derivatives [V-VIII] were tested for their antibacterial activity against Bacillus subtilis (G+) and Escherichia coli (G-) by agar well diffusion process, and the results showed that all polymers had a greater diameter of the growth inhibition region. This may be relative to the presence of sulfamethizole medication, maleimide group and Schiff bases, Polymer[V] demonstrated excellent inhibition against Bacillus subtilisa and E.coli.

Synthesis and Antibacterial Evaluation of 1,3-Benzoxazepine-1,5-diones bearing Benzothiazole Moiety

Azo-aldehyde derivative (2) was prepared through reaction of 2-hydroxybenzaldehyde with diazonium ion generated from 2-aminobenzothiazole (1). The producing aldehyde (2) was then treated with some anilines consisting (4-nitroaniline, 3-nitroaniline, 4-aminophenol, 4-methoxyaniline, 4-bromoaniline, 4-chloroaniline and 2,4-dichloroaniline) by (MW) method to give seven Schiff bases (3a-g). Cyloaddition reactions of Schiff bases (3a-g) and phthalic anhydride utilizing (MW) means in dry benzene yielded seven new 1,3-benzoxazepine-1,5-diones (4a-g) carrying the unit of benzothiazole. Determination of verves of final benoxazepines athwart bacteria done on Staphylococcus aurous (Gram-positive) and Escherichia coli (Gram-negative). The outputs showed that all benzoxazepine compounds exhibited greater activity to standard antibiotic (gentamycin) athwart Staphylococcus aurous. Moreover, the benzoxazepines (4a, 4b, 4c, 4d, 4e and 4g) appeared best activity athwart Escherichia coli comparably with that of standard antibiotic.

Model-based zero emission safety concept for reactors with exothermal reactions for chemical plants

To avoid major accidents caused by runaway reactions, a new safety concept called SmartHIP1 is introduced, with the objective to prevent runaway reactions and avoid emissions. The basic principle is based on an online model-based approach by using safety instrumented systems. Different criteria exist for calculating the hazard potential of a runaway reaction and its early detection. The approaches of the literature from the last years are analysed and divided into three different groups: Divergence, Accumulation and Adiabatic Criterion. Each approach is compared to the other by applying it to an esterification reaction of acetic anhydride with methanol. The approaches are evaluated according to different requirements, like accuracy, wide range of application or reliability.

A novel and efficient four-component synthesis of chromen–based dithiocarbamate derivatives by homogeneous catalysts under solvent-free conditions

An efficient and one-pot procedure is described for the synthesis of a variety of derivatives of 1,2-dihydrobenzo[f]chromen-3-ones and 3,4-dihydrochromen-2-ones under solvent-free conditions via a pseudo-four-component domino reaction of acetic anhydride, aryl aldehydes, glycine-based dithiocarbamates, and phenols/naphthols in the presence of l-proline and H4[Si(W3O10)4].xH2O as green catalysts. All products were made under the green strategy for the synthesis of corresponding products with excellent yields (up to 94%) and diastereoselectivity.

Synthesis and Identification of Epoxy Derivatives of 5-Methylhexahydroisoindole-1,3-dione and Biological Evaluation.

Cyclic imides belong to a well-known class of organic compounds with various biological activities, promoting a great interest in compounds with this functional group. Due to the structural complexity of some molecules and their spectra, it is necessary to use several spectrometric methods associated with auxiliary tools, such as the theoretical calculation for the structural elucidation of complex structures. In this work, the synthesis of epoxy derivatives of 5-methylhexahydroisoindole-1,3-diones was carried out in five steps. Diels–Alder reaction of isoprene and maleic anhydride followed by reaction with m-anisidine afforded the amide (2). Esterification of amide (2) with methanol in the presence of sulfuric acid provided the ester (3) that cyclized in situ to give imides 4 and 4-ent. Epoxidation of 4 and 4-ent with meta-chloroperbenzoic acid (MCPBA) afforded 5a and 5b. The diastereomers were separated by silica gel flash column chromatography, and their structures were determined by analyses of the spectrometric methods. Their structures were confirmed by matching the calculated 1H and 13C NMR chemical shifts of (5a and 5b) with the experimental data of the diastereomers using MAE, CP3, and DP4 statistical analyses. Biological assays were carried out to evaluate the potential herbicide activity of the imides. Compounds 5a and 5b inhibited root growth of the weed Bidens pilosa by more than 70% at all the concentrations evaluated.

Cover Feature: Three‐Component Castagnoli‐Cushman Reaction of 3‐Arylglutaconic Acid Anhydrides, Carbonyl Compounds, and Ammonium Acetate: a Quick and Flexible Way to Assemble Polysubstituted NH‐δ‐lactams (Eur. J. Org. Chem. 11/2021)

The Cover Feature shows the synthesis of NH-δ-lactams through three-component Castagnoli–Cushman reaction of 3-arylglutaconic anhydrides with carbonyl compound and ammonium acetate. The way chemical building blocks are united to form the desired heterocyclic product is compared to the famous tile-matching Tetris game. More information can be found in the Communication by M. Krasavin et al.

Copper Supported onto Magnetic Nanoparticles as an Efficient Catalyst for the Synthesis of Triazolobenzodiazepino[7,1‐b]quinazolin‐11(9H)‐ones via Click N‐Arylation Reactions

AbstractA novel catalyst is designed and synthesized based on immobilization of copper onto modified magnetic nanoparticles. The catalyst was characterized by several characterization techniques. The catalyst was applied for the synthesis of a novel series of heterocyclic scaffold containing a 1,4‐benzodiazepine fused with a 1,2,3‐triazole ring and a quinazolin‐11(9H)‐one skeleton. The method is based on the direct synthesis of quinazolin‐11(9H)‐one ring by the reaction of isatoic anhydride (or anthranilic acid) and propargylamine, and an aldehyde, containing a leaving group on its aromatic ring. The reaction contains an in situ sequential click reaction of azide group with terminal alkyne and subsequent N‐arylation reaction to afford the final products. The method benefits various advantages, such as regioselectivity and high yield of the products. The reusability of the catalyst was evaluated and the results showed that the catalyst is highly reusable in 10 sequential reactions.

Collagen-Based Thiol-Norbornene Photoclick Bio-Ink with Excellent Bioactivity and Printability.

As the essential foundation of bioprinting technology, cell-laden bio-ink is confronted with the inevitable contradiction between printability and bioactivity. For example, type I collagen has been widely applied for its excellent biocompatibility; however, its relatively low self-assembly speed restricts the performance in high-precision bioprinting of cell-laden structures. In this study, we synthesize norbornene-functionalized neutral soluble collagen (NorCol) by the reaction of acid-soluble collagen (Col) and carbic anhydride in the aqueous phase. NorCol retains collagen triple-helical conformation and can be quickly orthogonally cross-linked to build a cell-laden hydrogel via a cell-friendly thiol-ene photoclick reaction. Moreover, the additional carboxyl groups produced in the reaction of carbic anhydride and collagen obviously improve the solubility of NorCol in neutral buffer and miscibility of NorCol with other polymers such as alginate and gelatin. It enables hybrid bio-ink to respond to multiple stimuli, resulting in continuous cross-linked NorCol networks in hybrid hydrogels. For the first time, the collagen with a triple helix structure and gelatin can be mixed and printed, keeping the integrity of the printed construct after gelatin's dissolution. The molecular interaction among giant collagen molecules allows NorCol hydrogel formation at a low concentration, which leads to excellent cell spreading, migration, and proliferation. These properties give NorCol flexible formability and excellent biocompatibility in temperature-, ion-, and photo-based bioprinting. We speculate that NorCol is a promising bio-ink for emerging demands in tissue engineering, regenerative medicine, and personalized therapeutics.

Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes

A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.

Synthesis of β-keto-sulfones using alkyl/aryl sulphinates in ionic liquids [bmim-BF4] as an efficient and reusable reaction medium

Synthesis of β-keto-sulfones using alkyl/aryl sulphinates in ionic liquids [bmim-BF4] as an efficient and reusable reaction medium

Recyclable High-Performance Epoxy-Anhydride Resins with DMP-30 as the Catalyst of Transesterification Reactions.

Epoxy-anhydride resins are widely used in engineering fields due to their excellent performance. However, the insolubility and infusibility make the recycling of epoxy resins challenging. The development of degradable epoxy resins with stable covalent networks provides an efficient solution to the recycling of thermosets. In this paper, 2,4,6-tris(dimethylaminomethyl)phenol (DMP-30) is incorporated into the epoxy-glutaric anhydride (GA) system to prepare high-performance epoxy resins that can be recycled below 200 °C at ordinary pressure via ethylene glycol (EG) participated transesterification. The tertiary amine groups in DMP-30 can catalyze the curing reaction of epoxy and anhydride, as well as the transesterification between ester bonds and alcoholic hydroxyl groups. Compared with early recyclable anhydride-cured epoxy resins, the preparation and recycling of diglycidyl ether of bisphenol A (DGEBA)/GA/DMP-30 systems do not need any special catalysts such as TBD, Zn(Ac)2, etc., which are usually expensive, toxic, and have poor compatibility with other compounds. The resulting resins have glass transition temperatures and strengths similar to those of conventional epoxy resins. The influences of GA content, DMP-30 content, and temperature on the dissolution rate were studied. The decomposed epoxy oligomer (DEO) is further used as a reaction ingredient to prepare new resins. It is found that the DEO can improve the toughness of epoxy resins significantly. This work provides a simple method to prepare readily recyclable epoxy resins, which is of low-cost and easy to implement.

Charge-reversal silver clusters for targeted bacterial killing.

Bacterial infections have become a common global health problem, causing a wide range of properties and life loss. The development of a highly efficient, low-toxicity and targeted bacterial agent is urgently needed. As a conventional antibacterial agent, silver nanoparticles have been used for a long time, but they are still unable to achieve targeted bacterial killing. Herein, we have prepared surface positively (Ag(+) nanoparticles) and negatively (Ag(-) nanoparticles) charged silver nanoparticles by reduction of AgNO3 to construct Ag(-)/Ag(+) clusters. The zeta potential of the Ag(-)/Ag(+) nanoclusters could be controlled by changing the ratio of Ag(-) nanoparticles to Ag(+) nanoparticles. The surface negatively changed silver nanoparticles were prepared from the reaction of methyl maleic anhydride with the amino on the surface positively changed silver nanoparticles. In the acidic environment, Ag(-) nanoparticles undergo charge reversal, and Ag(-)/Ag(+) clusters with negatively charged nanoparticles and big-size are transformed into positively charged nanoparticles with small size. The in vitro experimental results demonstrate that the positively charged nanoparticles can be well adsorbed on the negatively charged bacteria, exhibiting a high bactericidal ability. Furthermore, the in vivo skin wound healing experiment showed that the Ag(-)/Ag(+) clusters could serve as an efficient antibacterial agent to combat bacterial infection.