13623-58-0

Usage

Uses

Used in Pharmaceutical Industry:
1H-IMidazole, 4,5-dihydro-2-(4-Methylphenyl)is used as a key intermediate compound for the synthesis of benziamide compounds. These benziamide compounds serve as PPAR (Peroxisome Proliferator-Activated Receptor) agonists, which play a crucial role in regulating cellular differentiation, development, and metabolism. PPAR agonists have been found to be effective in treating various diseases, including diabetes, obesity, and atherosclerosis, making 2-(4-Methylphenyl)-4,5-dihydro-1H-imidazole an important compound in the development of new therapeutic agents.

InChI:InChI=1/C10H12N2/c1-8-2-4-9(5-3-8)10-11-6-7-12-10/h2-5H,6-7H2,1H3,(H,11,12)

Upstream product

• 126121-22-0 1-Nitroso-2-p-tolyl-4,5-dihydro-1H-imidazole 
• 52809-98-0 N-benzoyl-4-methylthiobenzamide 
• 107-15-3 ethylenediamine 
• 57774-66-0 N-(Ethoxycarbonyl)-4-methylbenzenethiocarboxamide 
• 104-85-8 para-methylbenzonitrile 
• 99-94-5 p-Toluic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 106-38-7 para-bromotoluene 
• 14939-05-0 1-phenyl-3-(4-methylphenyl)prop-2-yn-1-one 
• 589-18-4 4-Methylbenzyl alcohol 
• 36288-37-6 N-hydroxy-4-methylbenzenecarboximidoyl chloride 

Downstream Products

• 37122-50-2 2-(p-tolyl)imidazole 
• 61320-58-9 2-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-imidazole 
• 1451258-28-8 C₁₆H₁₅N₃O₂S 
• 1440421-58-8 C₁₆H₁₇N₃O₂S 
• 1440421-52-2 C₁₇H₁₆N₂O₂S 
• 1440421-43-1 C₁₇H₁₈N₂O₂S 
• 1440421-57-7 C₃₄H₃₇N₃O₆S 

Relevant academic research and scientific papers

Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid

The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation of nitriles with ethylenediamine. Both of the MSS-SO3H and MSS-SO3Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.

Green Synthesis of 2-Substituted Imidazolines using Hydrogen Peroxide Catalyzed by Tungstophosphoric Acid and Tetrabutylammonium Bromide in Water

Various 2-substituted imidazolines were constructed from aromatic aldehydes with ethylenediamine using hydrogen peroxide as an oxidant in water. Tungstophosphoric acid (HPW) was found to be active for this transformation due to its ubiquitous catalytic and oxidative nature, and further combination of tetrabutylammonium bromide (TBAB) made this transformation more efficient and attractive. It was found that the yields of the corresponding 2-substituted imidazolines were markedly influenced by the position and nature of the substituents on the phenyl ring. A plausible mechanism was also proposed to clarify this catalytic oxidative system.

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.

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.

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.

Pd-catalyzed N-arylation of 2-imidazolines provides convenient access to selective cyclooxygenase-2 inhibitors

The re-emergence, in the recent years, of cyclooxygenase as a biological target in therapeutic areas other than inflammation is likely to require new optimized leads, particularly suited for the requirements of specific drug development programs. We devel

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.

Dissecting alkynes: Full cleavage of polarized C≡C moiety via sequential bis-michael addition/retro-mannich cascade

The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to the full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one π and two σ). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative nN → σ*C-C interaction.