61033-70-3

Usage

Chemical class

Imidazole derivatives

Physical form

Yellow crystalline solid

Molecular weight

208.187 g/mol

Uses

Synthesis of pharmaceuticals, organic compounds, agrochemicals, and dyes; building block in the production of various compounds

Biological activities

Antibacterial and antifungal properties

Importance

Valuable compound in the field of medicinal chemistry.

Upstream product

• 126121-25-3 2-(4-Nitro-phenyl)-1-nitroso-4,5-dihydro-1H-imidazole 
• 107-15-3 ethylenediamine 
• 62-23-7 4-nitro-benzoic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 619-73-8 4-nitrobenzyl chloride 
• 1184662-59-6 3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one 
• 2735-14-0 1,2-bis(4-nitrophenyl)acetylene 
• 619-72-7 4-nitrobenzonitrile 
• 259137-26-3 1-(4-methoxyphenyl)-2-(4-nitrophenyl)-4,5-dihydroimidazole 
• 122-04-3 4-nitro-benzoyl chloride 
• 51816-15-0 N-(2-chloroethyl)-4-nitrobenzamide 
• 126121-23-1 1-nitroso-2-phenyl-4,5-dihydro-1H-imidazole 

Downstream Products

• 555-16-8 4-nitrobenzaldehdye 
• 1614-06-8 2-(4-nitrophenyl)imidazole 

Relevant academic research and scientific papers

Visible Light-Promoted Aryl Azoline Formation over Mesoporous Organosilica as Heterogeneous Photocatalyst

N-heterocyclic compounds demonstrate wide applications ranging from natural compound production to coordination chemistry. Usually, the synthesis of N-heterocyclic compounds is conducted under thermal conditions, mostly by Lewis acids or metal-containing compounds as molecular catalysts. Here, we report a photocatalytic route for aryl azoline formation by mesoporous organosilica as visible light-active and heterogeneous photocatalyst. Via formation of aromatic aldehydes with various amines, 2-phenyl-2-imidazoline, 2-phenyl-2-oxazoline, 2-phenyl-2-thiazoline and their derivatives could be formed with high conversion and selectivity. Additionally, the organosilica photocatalyst showed high stability and reusability.

Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine

Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.

Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst

In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.

Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetic nanoparticles: A novel catalyst for the synthesis of imidazole derivatives under solvent-free conditions

New Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetite nanoparticles were prepared using a co-precipitation method and were used in the syntheses of imidazole derivatives under solvent-free conditions. The polyionene was easily prepared by reacting DABCO and 1,4-dibromo butane in DMF/methanol. It was then added to the previously formed layers and magnetic core-shell nanoparticles (P-MNPs) were functionalized. All the resultant nanoparticles were characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and vibrating sample magnetometry (VSM). The catalyst was readily recovered by simple magnetic decantation and can be recycled several times with no significant loss of catalytic activity.

Ruthenium(II) carbonyl complexes containing pyridoxal thiosemicarbazone and trans-bis(triphenylphosphine/arsine): Synthesis, structure and their recyclable catalysis of nitriles to amides and synthesis of imidazolines

Pyridoxal N(4)-substituted thisemicarbazone hydrochloride ligands (L1-3) were synthesized and reacted with the ruthenium(II) starting complexes [RuHCl(CO)(EPh3)3] (EP or As). The resulting complexes [Ru(CO)(L1-3)(EPh3)2] (1-6) were characterized by elemental analyses and spectroscopic techniques. The molecular structure of complex 5 was identified by means of single crystal X-ray diffraction analysis. The catalytic activity of the new complexes was evaluated for the selective hydration of nitriles to primary amides and also the condensation of nitriles with ethylenediamine under solvent free conditions. The processes were operative with aromatic, heteroaromatic and aliphatic nitriles, and tolerated several substitutional groups. The studies on the effect of substitution over thiosemicarbazone, reaction time, temperature, solvent and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favourable reaction conditions. A probable mechanism for both the catalytic reactions of nitrile has also been proposed. The catalyst was recovered and recycled in the hydration of nitriles for five times without any significant loss of its activity.

Efficient synthesis of 2-imidazolines in the presence of molecular iodine under ultrasound irradiation

An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25-30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.

Semi-empirical computation on mechanism of imidazolines and benzimidazoles synthesis and their QSAR studies

A green, mild and anaerobic synthesis of imidazolines and benzimidazoles from aldehydes and diamines using I2/KI/K2CO3/H2O system has been investigated by semi-empirical methods. The observed efficient direction of the above synthesis has been modeled from a comparison of the energies of four possible transition states arising from mono and di additions of iodines in the configured molecules. In the reaction I1 B is the most favorable transition state [TS] which is shown to be 20 Kcal/mol by PM3 analyses. The resulting trends of relative transition states energies are in excellent agreement with the experimental observations. Also, the bond order, bond length, heat of formation is in good agreement to the formation of product B. In order to establish the suitable mechanism of the reaction a quantitative structure activity relationship analysis has been made using hydrophobicity as the molecular descriptor. In this analysis the values of refractivity, polarizability, hydration energy, electron affinity, ionization potential and dipole moment of the compounds have been correlated with their hydrophobicity which has been taken as the molecular property.

COMPOUNDS FOR TREATMENT OF CANCER

The present invention relates to pharmaceutical compositions for treating cancer comprising BRAF inhibitors, (e.g. vemurafenib) and/or MEK inhibitor, (e.g. trametinib, RO5068760), in combination with anti-tubulin compounds of the invention or other known tubulin inhibitors, and using such compositions for treating cancer such as melanoma, drug-resistant cancer, and cancer metastasis.

Microwave mediated solvent free synthesis of 2-arylimidazolines from aldehydes using a solid base catalyst

2-Aryl imidazolines have been synthesized in solvent free condition using a catalytic amount of solid base (500mg) and by exposure to microwave. Ketones are not affected under these reaction conditions. Reaction time is short, clean products have been obtained and recovery is simple. The yields of the products are good.

Efficient and one-pot catalytic synthesis of 2-imidazolines and bis-imidazolines with p-toluenesulfonic acid under solvent free conditions

A practical, efficient, and inexpensive method for the synthesis of 2-imidazoline from the reaction of nitriles with ethylenediamine or 1,2-propanediamine using p-toluenesulfonic acid or pyridinium p-toluenesulfonate under reflux conditions is reported. This catalyst can be successfully applied for the chemoselective conversion of dicyanobenzenes to corresponding mono- and bis-imidazolines. The applications of these catalysts are feasible because of easy preparation, easy handling, stability, inexpensive, good activity, and eco-friendly.