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Usage

Uses

Used in Pharmaceutical Industry:
1H-Imidazole, 2-(2,4-dichlorophenyl)-4,5-dihydrois used as an antifungal agent for the treatment of yeast infections and athlete's foot. It functions by disrupting the production of ergosterol, a vital component of the fungal cell membrane, which leads to the inhibition of fungal growth and replication.
Used in Research and Laboratory Settings:
This chemical compound is also utilized as a research tool for studying the effects of imidazole derivatives on various biological processes. Its unique structure allows scientists to investigate its interactions with biological systems and potentially discover new therapeutic applications.

Upstream product

• 874-42-0 2,4-dichlorobenzaldeyhde 
• 107-15-3 ethylenediamine 

Relevant academic research and scientific papers

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.

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.

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.

A facile and efficient synthesis of 2-imidazolines from aldehydes using hydrogen peroxide and substoichiometric sodium iodide

The reaction of aldehydes with ethylenediamine for the preparation of 2-imidazolines has been studied using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate. A mild, green, and efficient method is established to carry out this reaction in high yield. Georg Thieme Verlag Stuttgart · New York.

Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors

A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO)2-3,4-Ph; (MeO)3-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development.

An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water

The system, I2/KI/K2CO3/H2O, oxidizes carbon-nitrogen bonds for the synthesis of imidazolines and benzimidazoles from aldehydes and diamines under anaerobic conditions in water at 90°C with excellent yields. The process is green, mild and inexpensive.