14599-72-5

Usage

Type of compound

Organic compound

Derivative of

Imidazolidinone

Structural feature

Contains a methoxy group attached to the meta position of a phenyl ring

Industrial applications

a. Pharmaceutical intermediate
b. Synthesis of other organic compounds

Biological activities

a. Antimicrobial properties
b. Anti-inflammatory properties

Potential uses

a. Development of new materials
b. Chemical reagent in organic synthesis

Range of applications

Industrial and biological due to unique chemical structure and properties

InChI:InChI=1/C10H12N2O2/c1-14-9-4-2-8(3-5-9)12-7-6-11-10(12)13/h2-5H,6-7H2,1H3,(H,11,13)

Upstream product

• 120-93-4 imidazolidone 
• 766-85-8 3-methoxy-1-iodobenzene 
• 18523-47-2 3-azidopropanoic acid 
• 536-90-3 m-Anisidine 
• 110-70-3 N,N`-dimethylethylenediamine 
• 14088-85-8 N¹-(3-methoxyphenyl)ethane-1,2-diamine 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1225208-19-4 C₁₈H₂₇N₃O₂ 
• 92491-23-1 4,5-dihydro-1-(3-methoxyphenyl)-3-methylimidazol-2(1H)-one 

Relevant academic research and scientific papers

PYRROLIDINE COMPOUNDS

The present invention provides compounds of the Formula (I) wherein L is selected from the group consisting of -CH2NHCH2-, -CH2NH-, -NH-, -S-, -S(O)-, -S(O)2-, -O-, -OCH2-, -OCH2CH2O-, -NHSO2NH-, (II) and (III), or a pharmaceutically acceptable salt thereof; a compound of the formula: (IV), processes for preparing the compounds and their salts, a pharmaceutical composition, and methods of treating patients in need of such treatment.

Nucleophilic substitution of azide acting as a pseudo leaving group: One-step synthesis of various aza heterocycles

The reaction of 3-azidopropanoic acid with the carbodiimide-based coupling reagent DIC leads to a six-membered-ring intermediate acting as a versatile precursor to a diverse set of aza heterocycles, including mono-, bi-, and tricyclic compounds.

Mild, convenient and versatile Cu-mediated synthesis of N-aryl-2-imidazolidinones

A mild, general, convenient and practical methodology for the selective copper-mediated mono N-arylation of unprotected 2-imidazolidinone was developed. Strong electron-donating groups and free hydroxy and amino groups on the aryl iodide substrates were well tolerated. The use of n-butanol as the solvent for the copper-catalysed mono-arylation of 2-imidazolidinone is unprecedented.

Lithiation of 1-arylimidazol-2(1H)-ones and 1-aryl-4,5-dihydroimidazol- 2(1H)-ones

1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.

Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds

The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.