16112-38-2

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 106-49-0 p-toluidine 
• 134-81-6 benzil 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 631-61-8 ammonium acetate 
• 104-85-8 para-methylbenzonitrile 

Relevant academic research and scientific papers

One-pot synthesis of tri- and tetra-substituted imidazoles using sodium dihydrogen phosphate under solvent-free conditions

Sodium dihydrogen phosphate (NaH2PO4) efficiently catalyzes the condensation reaction of benzil, aldehydes, amines and ammonium acetate in a four-component reaction under solvent-free conditions. The reaction proceeds rapidly and affords the corresponding tetra-substituted imidazoles in high yields. Also an efficient route was developed for the synthesis of tri-substituted imidazoles from condensation of benzil, aldehydes and ammonium acetate using NaH2PO4.

Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions

In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40-70 min for trisubstituted imidazoles and 30-40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92-98% for trisubstituted imidazoles and 94-98% for tetrasubstituted imidazoles) in simple multicomponent reactions. The structure of these products was confirmed via FT-IR and NMR. Green and recyclable catalysts, eco-friendly and solvent-free conditions, high catalytic activity, shorter reaction time, easy recovery by an external magnet, high purity, and excellent yields are some features of these reactions.

Ag–TiO2 nanocomposite-catalyzed one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles: a green and benign approach

Ag–TiO2 nanocomposite as an efficient catalyst was synthesized and characterized by AFM analysis. This nanocomposite acts as a heterogeneous and recyclable catalyst for the room temperature synthesis of 1,2,4,5-tetrasubstituted imidazoles from aldehydes, benzil, ammonium acetate and several anilines or aliphatic amines via one-pot four-component condensation reaction in H2O as a green solvent. Ag–TiO2 nanocomposite was simply recovered by filtration and was reused up to three times.

Sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles: a high-loaded and magnetically separable acid catalyst for multicomponent reactions

Abstract: In this study, a PVAm-bearing SO3H groups/Fe3O4 nanocomposite was prepared via a simple and in situ polymerization of acrylamide onto the surface of magnetic nanoparticles without using organosilane precursors. In order to obtain amine-functionalized magnetic, Hofmann degradation was carried out. In the following, sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles was prepared by covalent grafting of chlorosulfonic acid on amine groups. The introduction of polymer to the surface of magnetic nanoparticles increases the loading content with functional groups extremely. The resulting hybrid material was effectively employed as an unprecedented acid magnetic catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions. High yields, mild reaction conditions, short reaction times, operational simplicity with reusability are the notable features of the catalyst. The structure of the newly developed catalyst was characterized using TGA, FT-IR, SEM, TEM, VSM, EDX, CHNS, and XRD analysis. Magnetic separation and recycling of the catalyst for at least 8 runs is possible without any significant deterioration in catalytic activity. This work is the first report of employing PVAm as a linker for immobilizing liquid acid on a support.

One-pot synthesis of multisubstituted imidazoles catalyzed by Dendrimer-PWAn nanoparticles under solvent-free conditions and ultrasonic irradiation

An efficient, green and eco-friendly protocol has been developed for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles via one-pot condensation reaction using Dendrimer-PWAn as catalyst under solvent-free conditions or ultrasonic irradiation in excellent yields. The reactions under conventional heating conditions were compared with the ultrasonic-assisted reactions. The operational simplicity, practicability and applicability of this protocol to various substrates make it an interesting alternative to previous procedures. The present methodology offers several advantages such as excellent yields, short reaction times, a cleaner reaction, and the absence of any tedious work-up or purification. The catalyst is easily separated from the products by filtration and also exhibits remarkable reusable activity. SEM, BET and DLS of the catalyst were also investigated after each reaction cycle.

Appel reagent as novel promoter for the synthesis of polysubstituted imidazoles

We present an efficient method for the synthesis of polysubstituted imidazoles in the presence of Appel reagent (Ph3P/CCl4). Tri-substituted imidazoles is synthesized via condensation of aldehydes, benzil and ammonium acetate, and tetra-substituted imidazole is prepared via condensation of aldehydes, benzil, ammonium acetate and primary amines. These protocols allow the simple preparation of the desired products using readily available reagent instead of complex, expensive and toxic reagents under mild reaction conditions in excellent yields.

Synthesis of silyl-protected terminal thioalkyne-substituted tetraaryl imidazoles: utilization of Ag–Fe/ZSM-5 bimetallic nanooxides for cyclocondensation of polysubstituted imidazoles

An improved one-pot and ecofriendly approach to tri- and tetraaryl imidazoles through three- and four-component coupling reactions under neutral and solvent-less solid-phase conditions is presented. A series of nanosized Ag/metal oxide species on H–ZSM-5 support were tested in this procedure, with Ag–Fe/ZSM-5 bimetallic oxide nanoparticles exhibiting excellent catalytic activity for improved efficiency of the one-pot, multicomponent cyclocondensation reaction. The obtained bromoimidazole derivatives were converted into silyl-protected terminal alkynyl thiolate-substituted tetraaryl imidazoles by treatment with lithium 2,2,2-tris(trimethylsilyl)ethanedithioate, produced by reaction of organolithium reagent (Me3Si)3CLi with CS2 at 0?°C. These novel and stable synthetic intermediates are potential compounds for functionalization of imidazoles.

A waste to wealth approach through utilization of nano-ceramic tile waste as an accessible and inexpensive solid support to produce a heterogeneous solid acid nanocatalyst: To kill three birds with one stone

Regarding the subject of waste products/materials, recycling or reusing has had a pivotal role on account of environmental and economic reasons. As a consequence, the essential task, nowadays, can be invention of new and practical pathways to reuse or even recycle them. In this framework, until now, recycling of some waste products such as tile wastes has not been taken into consideration; so, we were prompted by the possibility of recycling tile wastes in the catalytic direction. To this end, we use them as cost-effective, available, and nontoxic support materials for the heterogenization of sulfuric acid, in order to prepare the novel nano-ceramic tile waste supported sulfonic acid catalyst (nano-ceramic tile waste-SO3H or n-CTW-SA). This solid acid catalyst was well characterized through FT-IR, XRD, FE-SEM, EDX, TEM, TGA, BET, BJH, pH analysis and Hammett acidity function. The as-prepared nano-ceramic tile waste supported sulfonic acid catalyst proved to be an active heterogeneous catalyst in multicomponent reactions (MRCs) for the rapid and efficient one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in high yields and selectivity. In comparison with some other homogeneous and heterogeneous catalysts, nano-ceramic tile waste supported sulfonic acid displayed a greater activity. Moreover, being highly stable, inexpensive, accessible, retrievable, reusable, and having low toxicity are some other beneficial points of this catalyst.

A new more atom-efficient multi-component approach to tetrasubstituted imidazoles: One-pot condensation of nitriles, amines and benzoin

A new more atom-efficient multi-component approach for the synthesis of tetrasubstituted imidazoles via the one-pot condensation of nitriles, primary amines and benzoin has been described. Using this method, a wide range of structurally diverse nitriles and primary amines were successfully condensed with benzoin in glycerol in the presence of TFA under microwave irradiation at 120 °C and all the products were obtained in good to excellent yields with higher atom efficiencies in comparison with the commonly used four-component condensation of aldehydes, ammonium acetate, primary amines and benzil.

Synthesis of Novel Organosiliconsulfur-Containing Tetrasubstituted Imidazoles Sonocatalyzed by LaxSr1-xFeyCo1-yO3 Nanoperovskites

The one-pot synthesis of tetrasubstituted imidazoles by use of a series of LaxSr1-xFeyCo1-yO3 perovskites as catalysts is described. The La0.8Sr0.2Fe0.34Co0.66O3 nanocatalyst had the greatest activity in the heterogeneous cyclocondensation of an aldehyde, benzil, ammonium acetate, and a primary aromatic amine in water under ultrasonic irradiation. Some of the derivatives generated during this work were utilized as substrates for the synthesis in good yields of novel multifunctional tetrasubstituted imidazoles with Me3Si, C=S, and SH groups, via nucleophilic attack of tris(trimethylsilyl)methyllithium (TsiLi) at the carbon of carbon disulphide.