Aromatic Acid Chlorides Research Articles

Cooperative Cu/Pd-Catalyzed 1,5-Boroacylation of Cyclopropyl-Substituted Alkylidenecyclopropanes.

A Cu/Pd-cocatalyzed 1,5-boroacylation of cyclopropyl-substituted ACPs with B2pin2 and acid chlorides has been developed. Using cyclopropyl-substituted ACPs as the starting material, a broad range of 1,5-boroacylated products with multiple functional groups was prepared in good yields with excellent regio- and stereoselectively. Both aromatic and aliphatic acid chlorides were tolerated in this reaction.

Novel triazolo pyridine derivatives and their anti cancer activity

A series of novel triazole functionalized trifluoromethyl pyridine derivatives was prepared starting from pyridine 1. Compound 1 on reaction with sulphuric acid gave compound 2 which on chlorination followed by hydrazine hydrate and obtained compound 3 and 4. Compound 4 on reaction with diverse substituted aliphatic and aromatic acid chlorides produced amide derivatives 4a-h and 5a-h. All the final compounds were evaluated for anti cancer activity against four human cancer cell lines such as HeLa - Cervical cancer (CCL-2); COLO 205- Colon cancer (CCL-222); HepG2- Liver cancer (HB-8065); MCF7 - Breast cancer (HTB-22). Promising compounds 4f and 4g were identified.

Synthesis and anticonvulsive activity of new 1,3-diazaadamantane derivatives

The work is devoted to the synthesis and study of the neurotropic activity of some derivatives of 3,7-diazabicyclo/3.3.1/nonanes. For this, various 5,7-dialkyl, methylphenyl, diphenyl 1,3-diazaa-damantanes 1 were synthesized, which, upon interaction with acid chlorides of aliphatic, aromatic and heterocyclic acids, were converted into the corresponding 3,7-diazabicyclo/3.3.1/nonanes. The anticonvulsant activity of the synthesized compounds was studied. Among them, substances with pronounced anticorazole activity were identified.

Design of Multitarget Inhibitors as Tracheal Smooth Muscle Relaxants.

Asthma complications and adverse effects associated with steroidal therapy highlight the need for non-steroidal compounds intercepting asthmatic pathophysiology at multiple targets. The present investigation was carried out to evaluate the tracheal smooth muscle relaxant effect of virtually designed, combinatorially synthesized polyfunctional N-heteroarylamides. Virtual screening and molecular docking studies of designed compounds were performed using PyRx and AUTODOCK 4.2 software against molecular targets viz. FLAP, LTB4, and H1 receptor. Cross-validation of virtual screening results and active site, confirmation was performedusingVlife MDS software version 3.5. The combinatorial approach was used to synthesize designed compounds in which heterocyclic amines were reacted with substituted aromatic acid chlorides by nucleophilic substitution reaction to obtain a 5x5 mini-library. The structures of synthesized leads were confirmed by infrared and proton magnetic resonance spectroscopic analysis. Synthesized compounds were evaluated for their smooth muscle relaxation effect on isolated goat tracheal smooth muscle. Results were calculated as a percent decrease in contraction response observed using histamine and LTB4. The tested compounds produced anticipated tracheal smooth muscle relaxant activity. Based on the results of screening the structure-activity relationships (SAR) have been reported. Present study concluded that synthesized polyfunctional N-heteroarylamides have a tracheal smooth muscle relaxant effect. The mode of action is predicted from the analysis of virtual screening results. A good correlation was observed between virtual screenings and biological activities of lead molecules suggesting the rationale used to optimize the structural requirements of a ligand for selected targets is appropriate.

A Reductive Benzylation for Benzenes Using Aroyl Chlorides and Triethylsilane Catalyzed by Aluminosilicate-Stabilized Silyl Cations on Montmorillonite

AbstractWe discovered that the aluminosilicate-stabilized silyl cations, which were created from a solid-acid catalyst, the proton-exchanged montmorillonite, and Et3SiH, efficiently promoted the reductive benzylation of benzenes with aromatic carboxylic acid chlorides and Et3SiH in one pot.

Synthesis of some new 1,4-benzoxazine-pyrazoles in water as EGFR targeting anticancer agents

• A general and efficient synthesis • Eco-friendly water as solvent • Compounds 4c and 4n were shown comparable activity over four human cancer cell with the standard etoposide. • Compounds 4c and 4n displayed promising inhibitory activity on tyrosine kinase EGFR when compared with the standard Erlotinib. A general and efficient synthesis of some new 3,5-disubtituted 1,4-benzoxazine-pyrazole hybrids ( 4a-4n ) in eco-friendly water via a tandem Sonogashira coupling and cyclocondensation sequence from aromatic acid chlorides, 3-(3- oxo -2 H -benzo[ b ][1,4]oxazin-4(3 H )-yl)propanenitrile, and hydrazine hydrate was reported herein. Among them, the compounds 4c and 4n showed comparable activity against four human cancer cell lines like MCF-7 (breast), A549 (lung), HeLa (cervical), and PC3 (prostate) with the standard etoposide. In addition, the compounds 4b , 4e, 4i , and 4j exhibited promising activity against all the cell lines when compared with the etoposide. Moreover, the compounds 4c and 4n displayed promising inhibitory activity over tyrosine kinase EGFR when compared with the standard erlotinib.The results of in silico pharmacokinetic and docking studies of two most potent analogues 4c and 4n were also supported the consistent in vitro anticancer activity results.

Synthesis and Evaluation of new 4(3H)-quinazolinones derivatives as potential Anti-Inflammatory agents

Ten different 2, 7-disubstituted [1, 3, 4]-thiadiazolo [2, 3-b] quinazolin-5(4H)-ones were synthesized by action of 3-amino-2-mercaptoquinazolin-4(3H)-ones with various aliphatic and aromatic acid chloride in the presence of phosphorousoxy chloride. The newly synthesized compounds have been characterized by their analytical and spectral (IR, 1HNMR and Mass) properties. Further, they have been screened for their anti-inflammatory (in vitro and in vivo) by standard method.

Novel polyesters based on indazole moiety: Synthesis, characterization and applicability as efficient inhibitors for acidic X-65-steel corrosion

In this report, novel series of unsaturated polyesters Va­d and VIa­d containing indazole moiety were successfully prepared via interfacial polycondensation technique of indazole derivatives III and IV with different aromatic and aliphatic acid chlorides; isophthaloyl­, terephthaloyl­, adipoyl­, and sebacoyl chlorides. The prepared polyesters were categorized by elemental analyses, IR, 1H NMR, Mass spectra, GPC, Thermogravimetric (TGA), X-ray analyses (XRD), and therefore the morphology was examined by scanning microscopy (SEM). They showed high thermal stability and different morphology structure. The corrosion protection performance of prepared polyesters Va­d and VIa­d on X65­steel in molar oil of vitriol was assessed using potentiodynamic polarization (PDP), electrochemical impedance spectroscopy (EIS), and SEM. Electrochemical tests (EIS and PDP) displayed polymers could efficiently impede the X65­steel corrosion and acted as inhibitors of the mixed type. At the optimal dose of 150 mg/L, the protection capacities of Va-d and VIa-d polymers ranged from 86.9% to 97.8%. adsorption of Va­d and VIa­d followed the adsorption model of Langmuir isotherm. Surface morphology examination by SEM also revealed that Va­d and VIa­d polymers form an efficient block layer on the surface of X65­steel to separate the acidic solution.

Systematic study on acylation of methyl 3-aminocrotonate with acid chlorides of aliphatic, aromatic and α, β-unsaturated acids: A comparative evaluation of the preference for regio- and stereoselectivity vis-à-vis 3-aminocrotononitrile

Acylation of methyl 3-aminocrotonate 1a in benzene with a variety of aliphatic and aromatic acid chlorides including α, β-unsaturated acid chloride in the presence of an added organic base, (either pyridine or triethylamine) is reported. The preferred N, C-site selectivity in these reactions has been compared with the terminal selectivity of the products obtained previously on acylation of methyl 3-aminocrotononitrile 1b . A strong preference either for N- or C- selectivity in N, C-acylation has been observed for both 1a and 1b based on the choice of acid chlorides and added organic base. Interestingly, irrespective of the enamine 1a or 1b , acylation with α, β-unsaturated acid chlorides in the presence of triethylamine afforded 3,4-dihydropyridin-(2 H )-one via [3.3] sigmatropic rearrangement of the corresponding intermediary N(E)-enamide. Accrued results show methyl 3-aminocrotonate to be a better precursor for preparation of enamides (N-acylated products) whereas 3-aminocrotononitrile is found to be a preferred choice for preparation of enaminones (C-acylated products). An attempt is made to offer a preliminary theoretical interpretation for observed site selectivity.

Friedel–Crafts acylation of antiaromatic norcorroles: electronic and steric modulation of the paratropic current

The first ever Friedel–Crafts acylation of an antiaromatic macrocycle was performed for norcorrolatonickel(ii) reacting with aromatic or aliphatic carboxylic acid chlorides in the presence of AlCl3.

Synthesis, structure and properties of 7-((4-amino-5-thio-1,2,4-triazole-3-yl)methyl)-theophylline derivatives

The combination of derivatives of 1,2,4-triazole and theophylline creates fertile soil for biologically active substances. The use of these heterocyclic systems allows the use of simple chemical modification methods and available reagents. This determines the relevance of the chosen direction of scientific research. The aim of the work was to study synthesis methods and study the properties of heterocyclic systems containing theophylline and 1,2,4-triazole fragment in their structure, create a chemical variety that was interesting from a scientific point of view and was promising in the search for biologically active substances. Materials and methods . Theophylline was used as the starting material. Using alkylation reactions, hydrazinolysis, interaction with a carbon disulfide followed by heterocyclization with an excess of hydrazine hydrate, 7-((4-amino-5-thio-1,2,4-triazole-3-yl)methyl)theophylline was obtained. The following stages of the chemical conversion included alkylation reactions with haloalkanes, the formation of azomethine compounds by reaction with aromatic aldehydes, and the reaction with aromatic carboxylic acid chlorides. The structure of the obtained compounds was confirmed by data of elemental analysis, 1H NMR spectroscopy and IR-spectrophotometry. The individuality of substances was established by using high performance liquid chromatography with diode-array and mass spectrometric detection. Results . S-alkylderivatives of 7-((4-amino-5-thio-1,2,4-triazole-3-yl)methyl)-theophylline, Schiff bases and carboxamides were synthesized, their structure was proved, and physical properties were investigated. The synthesized compounds have been subjected to the in silico molecular docking study against the kinases of anaplastic lymphoma by using the 2XP2 ligand, lanosterol 14-α-demethylase by using the 3LD6 ligand, cyclooxygenase-2 by using the ligand 4Z0L which were downloaded from the protein data bank (PDB). Conclusions . Molecular docking has shown the ability of the synthesized compounds to influence the kinase activity of anaplastic lymphoma, cyclooxygenase-2 and lanosterol-14-α-demethylase.

A facile synthetic route and dual function of network luminescent porous polyester and copolyester containing porphyrin moiety for metal ions sensor and dyes adsorption

Abstract In this work, A novel optical metal ion sensor microporous polyesters and copolyesters containing porphyrin moiety as a monomeric unit in the main chain were successfully prepared by the interfacial condensation polymerization from 5,10,15,20-Tetrakis(4-hydroxyphenyl) porphyrin (Por-OH) and 5,10,15,20-Tetrakis(4-hydroxy-3-methoxyphenyl) porphyrin (Por-V) with aliphatic and aromatic acid chlorides derivatives (such as; adipoyl chloride, and azobenzene-4,4′-dicarboxylic chloride, respectively). These polyesters and copolyesters are characterized by FT-IR, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), X-ray diffraction, UV–Visible absorbance, fluorescence emission, and SEM measurements. The results show that our novel compounds are amorphous, have good thermal stability with high char yield and possess peaks similar to the porphynoid structure that make them good metal ion sensors with different metals ions (such as; Zn+2, Cu+2, Ni+2, Co+2, and Fe+3). Also, they can be used as dye adsorbents in aqueous solution and displayed amazing adsorption and selectivity toward cationic dye methylene blue (MB) over anionic sunset yellow (SY) in the dye's mixture.

Synthesis of Dibenzofuranone-Oxime Derivatives with Anticonvulsant, Antihypoxic, and Anti-Ischemic Activity

New dibenzofuranone-oxime derivatives were designed based on active structures of oxime esters. Compounds of the proposed group were synthesized using 3,4,6,7,8,9-hexahydrodibenzo[b,d]furan-1(2H)-one oxime and aromatic acid chlorides. The anticonvulsant activity of the new compounds was studied. The structure— activity relationship was analyzed. Compound 1a [3,4,6,7,8,9-hexahydrodibenzo[b,d]furan-1(2H)-one O-(3,4-dichlorobenzoyl)oxime] was the most active compound after i.p. injection to mice in the maximal electroshock test over a wide dose range of 20 – 100 mg/kg. Compound 1a at doses of 10 and 30 mg/kg exhibited antihypoxic activity in a hypoxia test with hypercapnia in a hermetic chamber and anti-ischemic activity at a dose of 10 mg/kg in a rat ischemic stroke model.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

Synthesis of aromatic polyketones by nonstoichiometric Friedel–Crafts polycondensation using AlCl3

Aromatic polyketones were successfully synthesized by Friedel–Crafts acylation using AlCl3 between aromatic dicarboxylic acid chlorides and 2,2′-dimethoxybiphenyl under both stoichiometric and nonstoichiometric conditions.

High optical transparency, low dielectric constant, and light color of organosoluble polyamides based on 10,10-bis[4-(4- amino-3-trifluoromethylphenoxy)phenyl]- 9(10H)-anthrone

A new aromatic diamine, 10,10-bis[4-(4-amino-3-trifluoromethylphenoxy)phenyl]-9( 10H)-anthrone (BATFPA), has been synthesized from anthrone via three-step procedure. Low-temperature polycondensation of BATFPA with various aromatic dicarboxylic acid chlorides produced novel fluorinated polyamides with moderate to high inherent viscosities of 0.75–1.03 dL/g while the weight-average molecular weight and number-average molecular weight were in the range of 66,000–74,000 and 37,000–41,000, respectively. Nearly, all the polymers were readily soluble in polar solvents, such as N,N-dimethyl acetamide (DMAc), N-methyl-2-pyrrolidinone, pyridine, and tetrahydrofuran, and afforded transparent, light-colored, and flexible films upon casting from DMAc solvent. These polymers had glass transition temperatures of 249–309°C, 10% weight loss temperatures of 486–517°C, and char yields of 53–61% at 800°C under nitrogen. All polymers were amorphous and their films exhibited tensile strengths of 64–86 MPa, tensile moduli of 1.8–2.2 GPa, and elongation at break of 10–18%. These polymers had dielectric constants ranging from 3.25 to 3.76 (100 Hz), low moisture uptake in the range of 0.72–1.18%, and high transparency with an ultraviolet–visible absorption cutoff wavelength in the 360–378 nm range.

Synthesis and Functionalization of Ynone-Based Tubular Microporous Polymer Networks and Their Carbonized Products for CO2 Capture

Ynone-based microporous polymer networks (YMPNs) were synthesized by the reaction of aromatic dicarboxylic acid chloride and alkyne groups under Sono-gashira cross-coupling reaction conditions. As the reaction proceeded in a mixture of toluene and triethylamine (TEA), tubular precipitates formed rapidly. The microscopic and XRD studies showed thatthe precipitates had a core-shell structure with a rod-shaped triethylammonium chloride (TEA-HC1) crystalline core and a polymeric shell. The core was removed by washing with methanol to provide a hollow polymeric tube. The TEA-HC1 rod formed in situ during the cross-coupling reaction and served as a template in forming the tubular morphology. YMPNs could be modified with ease because of the presence of highly reactive ynone groups. YMPNs were functionalized with ethylenediamine by the Michael-type addition reaction. The amino group functionalized YMPNs were used as precursors of nitrogen-doped porous carbons. The pyrolysis of the polymers at 800 °C produced microporous carbon materials withoutthe activation process. The carbon materials showed significantly enhanced Brunauer-Emmett-Teller (BET) surface areas and CO2 uptake capacities compared to their precursor polymers.

Synthesis of Diarylacetylenes Bearing Electron-Withdrawing Groups via the Smiles Rearrangement

Nitrobenzyl benzothiazol-2-yl sulfones and nitrobenzyl 1-phenyl-1H-tetrazol-5-yl sulfones react with chlorides of aromatic acids to form β-acyl derivatives. These products undergo the Smiles rearrangement resulting in the formation of the corresponding nitrophenyl arylacetylenes in 50–60% overall yields (approx. 75% per step). Sulfones bearing CF3 or CN groups instead of a NO2 substituent form mixtures of the acetylenes in moderate yields and benzyl aryl ketones in yields above 40%.

Kinetics of interfacial hydrolysis of an aromatic acid chloride

The interfacial hydrolysis of trimesolyl chloride (TMC) is studied in this work. TMC, together with meta-phenylene diamine (mPDA), forms the pair of monomers commercially used extensively in the preparation of thin film composite membranes for reverse osmosis. The interfacial hydrolysis of TMC is a side reaction in this process, and affects the kinetics of film formation and properties of the film that forms. Here, we develop a methodology for the kinetic study of this hydrolysis, and use it to determine and model the kinetics of hydrolysis of TMC. In order to provide the context, we first establish the circumstances under which it can be competitive with the main reaction. It is shown that pH has a significant effect on the kinetics of hydrolysis, and because of this, the hydrolysis can be self-limiting under most circumstances. The presence of a surfactant, often present in such systems, can influence the kinetics in significant ways. The kinetics has been modeled as a function of the reactant concentration and pH, and the model tested against experimental data obtained with different initial TMC concentrations, and at different concentrations of a commonly used surfactant, Tween 85.

Facile Synthesis and Antimicrobial Activity of 5‐Amino‐3‐methyl‐1‐phenyl‐1H‐thieno[3,2‐c]pyrazole‐6‐carbonitrile and Their Derivatives

5‐Amino‐thieno[3,2‐c]pyrazole derivative 2 was prepared by Gewald reaction in a one‐pot procedure. The amino group of compound 2 like primary aromatic amine formed the diazonium salt when treated with NaNO2/HCl, followed by coupling with different nucleophiles to yield the azo coupling products 3a–d. The reactivity of 5‐amino‐thienopyrazole 2 has been investigated towards different electrophilic reagents such as aromatic aldehydes, alkyl halide, acid chloride, acid anhydride, phenyl isothiocyanate, carbon disulfide, ethyl glycinate, and thioacetamide, which afforded the reaction products 4–14, respectively.