939-06-0

Usage

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

Upstream product

• 28861-84-9 Ethyl 3-chloro-2-cyano-3-phenylpropenoate 
• 78-90-0 1,2-diaminopropan 
• 26851-78-5 2-phenyl-3-methyl-Δ²-thiazolidinium iodide 
• 13758-35-5 3,4,4-trimethyl-2-phenyl-4,5-dihydro-oxazolium; iodide 
• 1568-96-3 4,4-dimethyl-2-phenyl-Δ²-oxazolinium chloride 
• 5873-90-5 methyl benzimidate hydrochloride 
• 93-58-3 benzoic acid methyl ester 
• 100-52-7 benzaldehyde 
• 2227-79-4 benzenecarbothioamide 
• 19312-06-2 4,5-dihydro-4,4-dimethyl-2-phenoxazole 
• 2722-34-1 2-phenylthiazoline 
• 936-49-2 2-phenyl-2-imidazoline 
• 100-47-0 benzonitrile 

Downstream Products

• 1227199-90-7 5-(4-bromophenyl)-2-methyl-5H-imidazo[2,1-a]isoindole 
• 1227199-92-9 5-(4-bromophenyl)-3-methyl-5H-imidazo[2,1-a]isoindole 
• 147428-55-5 (+/-)-5-methyl-1,2-diphenyl-4,5-dihydro-1H-imidazole 
• 1427476-06-9 (+/-)-4-methyl-1,2-diphenyl-4,5-dihydro-1H-imidazole 

Relevant academic research and scientific papers

Substituent changes in the salen ligands of CuIINaI-complexes to induce various structures and catalytic activities towards 2-imidazolines from nitriles and 1,2-diaminopropane

Based on various comparable salen ligands, three synthesized CuIINaI-complexes present efficient catalytic activities for the coupling and cyclization reaction of 1,2-diaminopropane with nitriles towards 2-imidazolines. The catalytic results show that salen ligands with an electron-donating substituent and small steric hindrance improve the catalytic activity.

On DABAL-Me3 promoted formation of amides

The range and utility of DABAL-Me3 couplings of methyl esters and free carboxylic acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic acids derivatives. The influence of microwave energy on the reaction system was shown to be typically related to thermal effects (over-pressuring and superheating).

Copper-catalyzed N -arylation of 2-imidazolines with aryl iodides

The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, ligand-free conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.

IMIDAZOISOINDOLE NEUROPEPTIDE S RECEPTOR ANTAGONISTS

The present invention is directed to imidazoisoindole compounds which are antagonists of neuropeptide S receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which the neuropeptide S receptor is involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the neuropeptide S receptor is involved.

Synthesis of Imidazoles and Imidazolines from 1,2-Diamines and Ethyl (E)- and (Z)-3-Aryl-3-chloro-2-cyanopropenoates

Ethyl (E)- and (Z)-3-aryl-3-chloro-2-cyanopropenoates react stereoselectively with 1,2-diamines at room temperature to give ethyl(Z)-3-(2-aminophenylamino)-3-aryl-2-cyanopropenoates. When the reactions are carried out at higher temperatures, cyclization takes place and imidazoles and imidazolines are formed in moderate to high yields.

1,2- and 1,3-Diamine Exchange between Substituted 4,5-Dihydroimidazoles and 1,4,5,6-Tetrahydropyrimidines: Routes to Benzimidazoles, Dihydroimidazoles, and Tetrahydropyrimidines

A range of 2-substituted 4,5-dihydroimidazoles and 2-substituted 1,4,5,6-tetrahydropyrimidines when heated with an excess of substituted ethane-1,2-diamines, o-phenylenediamines, and propane-1,3-diamine underwent diamine exchange to give 2-substituted heterocycles derived from the solvent diamine.The reaction was an equilibrium process favouring six-membered rings.The synthetic scope is amplified by the ready aromatisation of these partially reduced heterocycles.

CARBON TRANSFER REACTIONS OF Δ2-OXAZOLINIUM AND THIAZOLINIUM CATIONS

Δ2-Oxazolinium and thiazolinium cations with or without an appendage at any of the heteroatoms transfer their C(2) units at the carboxylic acid oxidation level to binucleophiles and provide the corresponding heterocycles, thus mimicking carbon transfer reactions exhibited by THF models, N-methyl N'-tosyl/acetyl imidazolinium cations.However, these azolinium cations react with phenethylamine and tryptamine to furnish their N-acyl derivatives.

Heterocyclic Ring Interchange Reactions

Δ2-Oxazolinium and thiazolinium cations transfer their C(2) units to acyclic binucleophiles to furnish ring interchange non-aromatic heterocycles.