Reaction Of Acyl Chlorides Research Articles

Nano CoCuFe2O4 catalyzed coupling reaction of acid chlorides with terminal alkynes: A powerful toolbox for palladium-free ynone synthesis

The present work describes the application of nano CoCuFe2O4 toward the coupling reaction of acyl chlorides with terminal alkynes. By this catalytic system, ynone derivatives were formed in high yields via a palladium-free strategy. This protocol avoids the use of phosphine ligands as well as toxic CO sources. Recovery of catalyst by employing an external magnetic field and its reuse up to 9 consecutive trials confirm the robustness of this catalytic system.

Synthesis of thiazole derivatives using magnetic nano zirconia–sulfuric acid as an efficient and recyclable catalyst in water

Fe3O4 magnetic core covered by zirconia shell bearing sulfonic acid groups (Fe3O4@ZrO2–SO3H) was prepared and used as an efficient acidic catalyst in the synthesis of thiazole derivatives by the reaction of acyl chloride with ammonium thiocyanate, amino acids and alkyl bromides. Fe3O4@ZrO2–SO3H exhibited high catalytic activity in the synthesis of thiazole derivatives. This new catalytic method for thiazole derivatives provided rapid access to the desired compounds in high yields in water media upon refluxing followed by a simple work-up procedure. The developed method is a significant improvement of the currently available synthetic approaches to thiazole derivatives.

Synthesis and Structural Characterization of 6-(N-Methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic Acid Methyl Ester Isomers

A series of monoamide isomers have been successfully synthesised and characterised using combination of common spectroscopic techniques such Fourier Transform Infrared (FT-IR), 1H and 13C Nuclear Magnetic Resonance (NMR) and Ultraviolet-visible (UV-vis). The monoamide compounds namely 6-(3-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L1), 6-(4-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L2), 6-(5-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L3) and 6-(6-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L4) were prepared from reaction between 6-(methoxycarbonyl)pyridine-2-carboxylic acid with 2-amino-N-methylpyridine (where N = 3, 4, 5 and 6) by using acyl chloride reaction. In this present studies, the synthesis and characterization of these compounds are discussed along with the inductive effects contributed by methyl substituted groups at the pyridine ring.

Polyamide thin film composite nanofiltration membrane modified with acyl chlorided graphene oxide

In order to reach both high water permeability and high ion rejection, a thin-film composite nanofiltration membrane (PA/GO-COCl) with acyl chlorided graphene oxide (GO-COCl) embedded in polyamide (PA) layer was fabricated by interfacial polymerization of piperazine and trimesoyl chloride. GO-COCl was synthesized by acyl chloride reaction with graphene oxide and then added into a nonpolar organic (hexane) phase using 2% ethanol as dispersant. The surface morphologies and chemical structures of the modified membranes were observed by scanning electronic microscopy, atomic force microscopy, X-ray photoelectron spectroscopy and FTIR spectroscopy. Water flux of the PA/GO-COCl membrane increased from 11.6 to 22.6Lm−2h−1, and salt rejection of Na2SO4 increased from 95.0% to 97.1%, compared with those of the pristine PA membrane. Enhanced performances of the PA/GO-COCl membrane were attributed to the incorporation of laminated graphene oxide sheets, which decrease effective thickness of the active layer and keep the layer intact for high rejection rate. This graphene oxide embedded membrane overcomes the trade-off effect of conventional thin film composite nanofiltration membranes, suggesting a novel method for fabricating 2D laminar materials embedded thin film composite membranes for nanofiltration or reverse osmosis.

Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp(3))-H arylation.

The synthesis of β-arylated alkylamides via alkyl C–H bond arylation has been realized by means of direct one-pot reactions of acyl chlorides, aryl iodides and 8-aminoquinoline. Depending on the structure of the starting materials, both single and double β-arylated alkylamides could be accessed.

ChemInform Abstract: Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Preparation of Pyrrolizine by Intramolecular Capture of Intermediates with Alkenes or Alkynes.

AbstractThe intramolecular capture of the corresponding isocyanate ions, generated from (I), (IV) and (VIII), as well as the N‐acyliminium ion from (VI) with alkene and alkyne units is described.

ChemInform Abstract: Sequential Multicomponent Synthesis of α‐Ketoimides, from Acyl Chlorides, Isocyanides, and Silver Salts of Carboxylic Acids.

AbstractThe sequential three component reaction of acyl chlorides, isocyanides, and silver carboxylates affords moderately stable keto‐iminoanhydrides which spontaneously undergo a Mumm rearrangement to produce the target α‐ketoimides (IX) and (XI).

Copper-catalyzed one-pot tandem reactions toward the synthesis of indoles using o-iodoanilines, acyl chlorides, and Wittig reagents

The one-pot reactions of acyl chlorides, Wittig reagents, and o-iodoanilines involving a copper-catalyzed C–C coupling have been realized to provide various indoles. The reactions proceed on the basis of the in situ generation of allenes to incorporate o-iodoanilines via tandem Michael addition, C–C coupling, and tautomerization to afford indoles. This direct one-pot protocol allows the synthesis of indoles with all easily available materials.

Polyethylene glycol-400/H3PO2: an eco-friendly reductive system for the synthesis of selanylesters

An alternative green method was described for the synthesis of selanylesters by reactions of acyl chlorides with arylselenols, generatedin situby reaction of diaryl diselenides with hypophosphorous acid (H3PO2) using polyethylene glycol-400 (PEG-400) as the solvent.

Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: preparation of pyrrolizine by intramolecular capture of intermediates with alkenes or alkynes.

The preparation of substituted pyrrolizines through the Schmidt reaction of acyl chlorides with alkyl azides has been realized. Intramolecular capture of the isocyanate ion and N-acyliminium ion intermediates from the Schmidt process with alkene or alkyne units was achieved, and the efficiency of the conversion with respect to ring construction and bond formation was demonstrated.

ChemInform Abstract: Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Capture of N‐Acyliminium Ion Intermediates with Aromatic Rings.

Intramolecular Schmidt reaction of acyl chlorides with alkyl azides through N-acyliminium ion intermediates is designed and realized. The intramolecular capture of the intermediates with aromatic rings affords several nitrogen-containing tricyclic skeletons. The important feature of the domino process is the efficiency in bond reorganization and ring formation.

Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: capture of N-acyliminium ion intermediates with aromatic rings.

Intramolecular Schmidt reaction of acyl chlorides with alkyl azides through N-acyliminium ion intermediates is designed and realized. The intramolecular capture of the intermediates with aromatic rings affords several nitrogen-containing tricyclic skeletons. The important feature of the domino process is the efficiency in bond reorganization and ring formation.

ChemInform Abstract: Palladium‐ and Solvent‐Free Synthesis of Ynones by Copper(I)‐Catalyzed Acylation of Terminal Alkynes with Acyl Chlorides under Aerobic Conditions.

AbstractAn easy, very efficient, and fast method for the cross‐coupling reaction of acyl chlorides with terminal alkynes is developed.

Copper-catalyzed three-component synthesis of 5-acetamidoimidazoles from carbodiimides, acyl chlorides and isocyanides

Only very limited methods are available for the synthesis of 5-amino imidazoles. We report in this paper that three-component reaction of acyl chlorides, carbodiimides and α-isocyanoacetates or TosMIC took place smoothly in the presence of Et3N (2.5 equiv.) and a catalytic amount of copper iodide (0.2 equiv.) to afford 1,4-disubstituted 5-acetamidoimidazoles in good yields.

A facile and rapid route for the synthesis of Cu/Cu2O nanoparticles and their application in the Sonogashira coupling reaction of acyl chlorides with terminal alkynes

This work reports a simple, rapid and efficient protocol for synthesis of Cu/Cu2O nanoparticles. The prepared Cu/Cu2O nanoparticles were effectively utilized for Sonogashira coupling reaction of acyl chlorides with terminal alkynes.

Preparation of a novel stabilizer and its thermal‐oxidative stabilization effect on polyamide 6

A novel stabilizer containing hindered phenol and hindered amine light stabilizer (HALS) group in one molecule was prepared through the acyl chloride reaction followed by the amidation reaction. Its structure was characterized by electrospray ionization mass spectrometry (ESI‐MS) and proton nuclear magnetic resonance (1H‐NMR), Fourier transform infrared spectroscopy (FT‐IR). The thermogravimetric analysis (TGA) results under nitrogen and air atmosphere indicated that the addition of the novel stabilizer efficiently improved the thermal and thermal‐oxidative stability of polyamide 6 (PA6). The thermal‐oxidative stabilization effect of the novel stabilizer on PA6 was further evaluated in terms of reduced viscosity, tensile properties, and chemical structure after accelerated thermal aging in an air circulating oven at 150°C. The results indicated that the novel stabilizer could improve the thermal‐oxidative stability of PA6 effectively, resulting in the high retention of reduced viscosity and tensile strength, and the low ratio of terminal carboxyl group to amino group. The mechanism of the novel stabilizer on the thermal‐oxidative stabilization of PA6 was also discussed. POLYM. ENG. SCI., 54:2197–2206, 2014. © 2013 Society of Plastics Engineers

ChemInform Abstract: An Efficient Method for the Preparation of Hydroxamic Acids.

Reactions of acyl chlorides with hydroxylamine hydrochloride and NaHCO3 generate the corresponding hydroxamic acid products in ethyl acetate and water at room temperature for 5 min. This is a simple and efficient method to synthesize a wide range of hydroxamic acids from carboxylic acids in excellent yield and high purity after simple post-treatment without chromatographic purification. In this process, the highlights are the simple separation of products and cheaply available reagents.

Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Rapid Access to Fused Polycyclic Nitrogen-Containing Heterocycles via a Multistep One-Pot Transformation

The first intramolecular Schmidt reaction of acyl chlorides with alkyl azides has been developed. In this one-pot conversion, an ω-azido hydrocinnamic acid is converted to a tricyclic lactam. The most important feature of the process is the efficiency in bond formation (one bond broken and three new bonds created) and ring construction (two new rings formed).

NaHSO4‐SiO2‐Promoted Solvent‐Free Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazole Derivatives

An efficient protocol has been developed for the preparation of a library of benzoxazole, benzimidazole, and benzothiazole derivatives from reactions of acyl chlorides with o‐substituted aminoaromatics in the presence of catalytic amount of silica‐supported sodium hydrogen sulphate under solvent‐free conditions. Simple workup procedure, high yield, easy availability, reusability, and use of ecofriendly catalyst are some of the striking features of the present protocol.

One-Pot Synthesis of 5-Acyl-2-amino-1,3,4-thiadiazoles

A novel two-step one-pot synthesis of 5-acyl-2-amino-1,3,4-thiadiazoles by the reaction of acyl chlorides with N-isocyanoiminotriphenylphosphorane in the presence of KSCN is described. It was found that THF and KSCN are the key reagents to obtain the desired products in high isolated yields.