Imidazoles In Water Research Articles

Practical and Selective Syntheses of S‐Acyl and N‐Acyl Glutathiones with N‐Acyl Imidazoles in Water

AbstractA selective, mild, convenient, and green protocol for the preparation of S‐acyl and N‐acyl glutathiones is described involving the chemical modification of glutathione (GSH) with N‐acyl imidazoles at room temperature in water. The syntheses of S‐acyl glutathiones were achieved in very high yields using 1 equiv. of an N‐acyl imidazole in water at room temperature, without the need of a base. Double acylation of GSH with various N‐acyl imidazoles in weakly basic aqueous media in the presence of N‐hydroxysuccinimide (HOSu) as the activating reagent followed by selective deprotection of the S‐acyl group with aqueous ammonia at room temperature gave high yields of N‐acyl glutathiones. Moreover, the reaction could accommodate a diverse range of carboxylic acids such as (hetero)benzoic acids, phenylacetic acids, aliphatic acids from short‐chain fatty acids (including acetic acid), long‐chain polyunsaturated fatty acids, secondary or tertiary amino acids, and carboxylic acids containing clickable functional groups, fluorescent probes, or drugs.

An eco-compatible pathway to the synthesis of mono and bis-multisubstituted imidazoles over novel reusable ionic liquids: an efficient and green sonochemical process.

Novel and environmentally benign ionic liquids (ILs) comprised of DABCO were successfully synthesized. These ILs were used as robust catalysts for the sonochemical one pot multi-component synthetic route for the functionalized annulated imidazoles in water with excellent yields. The present protocol scored well in terms of yield economy as compared with the conventional procedures. The merits of the current green method include simplicity, applicability, broad functional groups tolerance, clean reaction profiles, and no tedious work-up and they give high-to-quantitative yields. From the environmental viewpoint, these eco-friendly green catalysts can be effortlessly retrieved and reused at least seven successive times without substantial loss in catalytic activity.

EDTA Catalyzed Green Protocol for Multicomponent Synthesis of Some Novel Highly Substituted Imidazoles in Water

The multicomponent reaction of N-substituted isatin derivatives with ammonium acetate and substituted aromatic aldehydes in the presence of catalytic amount of EDTA readily gives rise to substituted imidazoles under controlled microwave irradiation in water. The presented method is mild, environmentally friendly, inexpensive and highly effective to give the products in good to excellent yields. The chemical structures of the respective synthesized compounds were confirmed by analytical and spectral data.

ChemInform Abstract: A Simple and Efficient 2N2O‐Cu(II) Complex as a Catalyst for N‐Arylation of Imidazoles in Water.

AbstractFour inexpensive and air‐ and moisture‐stable 2N2O—Cu complexes are synthesized, one of them shows good catalytic activity for the N‐arylation of imidazoles in water.

A simple and efficient 2N2O–Cu(II) complex as a catalyst for N‐arylation of imidazoles in water

Four inexpensive and air‐ and moisture‐stable 2N2O–Cu complexes were synthesized, one of which proved to exhibit good catalytic activity for the N‐arylation of imidazoles in water. A variety of aryl iodides and aryl bromides underwent coupling with imidazoles promoted by the catalytic system with moderate to excellent yields. Copyright © 2015 John Wiley & Sons, Ltd.

ZnO nanorods: Efficient and reusable catalysts for the synthesis of substituted imidazoles in water

A simple procedure has been developed for the synthesis of ZnO nanorods (ZnO NRs). The newly synthesized crystals were characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). Moreover, the catalytic activity was examined in the one-pot, three-component synthesis of 2,4,5-triaryl-1H-imidazoles in water under reflux conditions. The results confirmed ZnO NRs to be mild, benign and effective catalysts for the preparation of tri-substituted imidazoles in high yield via an operationally simple and environmentally friendly procedure. Furthermore, the catalyst can be conveniently recovered and reused for at least three runs without any activity loss.

ChemInform Abstract: Copper Powder‐Catalyzed N‐Arylation of Imidazoles in Water Using 2‐(Hydrazinecarbonyl)pyridine N‐Oxides as the New Ligands.

AbstractThe novel catalytic system allows the N‐arylation of imidazole and pyrrole with aryl iodides and bromides in water as the solvent without the need for an inert atmosphere.

Copper powder-catalyzed N-arylation of imidazoles in water using 2-(hydrazinecarbonyl)pyridine N-oxides as the new ligands

2-(2-Hydrazinecarbonyl)pyridine N-oxides, which were derived from pyrrole-2-carbohydrazides and pyridine N-oxides, were synthesized and utilized as the ligands for copper powder-catalyzed N-arylation of imidazoles with aryl halides in water. Imidazoles could be arylated smoothly with various aryl halides to provide the title products in preferable yields without the need of an inert atmosphere.

ChemInform Abstract: Efficient Copper‐Catalyzed Ullmann Reaction of Aryl Bromides with Imidazoles in Water Promoted by a pH‐Responsive Ligand.

A series of 1,10-phenanthroline derivatives were used as supporting ligands for copper-catalyzed Ullmann reaction in neat water. The catalytic system based on 4,7-dihydroxy-1,10-phenanthroline has demonstrated the promising catalytic performances for aryl bromides. The catalytic system was applicable to a wide scope of substrates, high catalytic activity and selectivity were observed for the reactions of electron-deficient, electron-rich, and heterocyclic aryl bromides with imidazoles containing different steric hindrance. The superior promoting effect of 4,7-dihydroxy-1,10-phenanthroline is attributed to its water solubility under the basic conditions.

Efficient Copper‐Catalyzed Ullmann Reaction of Aryl Bromides with Imidazoles in Water Promoted by a pH‐Responsive Ligand

AbstractA series of 1,10‐phenanthroline derivatives were used as supporting ligands for copper‐catalyzed Ullmann reaction in neat water. The catalytic system based on 4,7‐dihydroxy‐1,10‐phenanthroline has demonstrated the promising catalytic performances for aryl bromides. The catalytic system was applicable to a wide scope of substrates, high catalytic activity and selectivity were observed for the reactions of electron‐deficient, electron‐rich, and heterocyclic aryl bromides with imidazoles containing different steric hindrance. The superior promoting effect of 4,7‐dihydroxy‐1,10‐phenanthroline is attributed to its water solubility under the basic conditions.

ChemInform Abstract: Synthesis of 2,4,5‐Trisubstituted and 1,2,4,5‐Tetrasubstituted Imidazoles in Water Using p‐Dodecylbenzenesulfonic Acid as Catalyst.

2,4,5-Trisubstituted imidazoles have been synthesized by treatment of benzil with aldehydes and ammonium acetate in water under reflux in the presence of p-dodecylbenzenesulfonic acid as catalyst. The same reaction using an additional amine affords 1,2,4,5-tetrasubstituted imidazoles. The products are formed in high yields within 4 h under eco-friendly conditions.

ChemInform Abstract: Efficient Use of a Surfactant for Copper‐Catalyzed Coupling Reaction of Arylboronic Acids with Imidazoles in Water.

AbstractCopper‐catalyzed oxidative coupling of arylboronic acids with imidazoles can be performed in water just using an amphiphilic surfactant.

Ultrasound-promoted synthesis of (4 or 5)-aryl-2-aryloyl-(1H)-imidazoles in water

Article history: Received March 27, 2013 Received in Revised form August 27, 2013 Accepted 14 September 2013 Available online 14 September 2013 A green and efficient method for the synthesis of (4 or 5)-aryl-2-aryloyl-(1H)-imidazoles via self-condensation reaction of arylglyoxal hydrates in the presence of ammonium acetate using water as solvent under ultrasonic irradiation was reported. The reactions proceeded in high yields and very short reaction time. Introduced procedure is completely ecofriendly and don’t need any toxic organic solvent in all performing steps. In addition, we use computational chemistry for acquiring some information about the thermochemistry and geometrical structure of these imidazole derivatives. © 2013 Growing Science Ltd. All rights reserved.

Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water

Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-free conditions, providing an efficient, practical, and greener method for the synthesis of N-arylimidazoles.

Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in water using p-dodecylbenzenesulfonic acid as catalyst

2,4,5-Trisubstituted imidazoles have been synthesized by treatment of benzil with aldehydes and ammonium acetate in water under reflux in the presence of p-dodecylbenzenesulfonic acid as catalyst. The same reaction using an additional amine affords 1,2,4,5-tetrasubstituted imidazoles. The products are formed in high yields within 4 h under eco-friendly conditions.

ChemInform Abstract: Simple Synthesized Mannich Bases as Ligands in Cu‐Catalyzed N‐Arylation of Imidazoles in Water.

AbstractA simple, environmentally friendly and efficient protocol for the N‐arylation of imidazoles and related N‐heterocycles is developed.

Simple synthesized Mannich bases as ligands in Cu-catalyzed N-arylation of imidazoles in water

1,4-Bis(2-hydroxy-5-methoxybenzyl)piperazine and its analogues were used as efficient ligands for CuI-catalyzed N-arylation of imidazoles with aryl halides in water under mild conditions (120 °C for 12 h) with 10 mol% of CuI, 20 mol% of the Mannich base, and two equivalents of KOH or K2CO3 in the presence of 10 mol% phase transfer catalyst (n-Bu)4NBr. A variety of products were synthesized in moderate to excellent yields using this inexpensive catalytic system.

ChemInform Abstract: Novel One‐Pot Synthesis of (4 or 5)‐Aryl‐2‐aryloyl‐(1H)‐imidazoles in Water and Tauto‐Isomerization Study Using NMR.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Pyridine N‐Oxides as Ligands in Cu‐Catalyzed N‐Arylation of Imidazoles in Water.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A Simple and Efficient Catalytic System for N‐Arylation of Imidazoles in Water

A Simple and Efficient Catalytic System for N‐Arylation of Imidazoles in Water