6844-34-4

Upstream product

• 6843-49-8 5-methyl-5-phenylimidazolidin-2,4-dione 
• 75356-43-3 1-(Cyano-methyl-phenyl-methyl)-3-methyl-urea 
• 29738-08-7 racem-α-Methyl-α-cyan-benzylisocyanat 
• 98-86-2 acetophenone 
• 74-88-4 methyl iodide 
• 1462367-32-3 1-[(4-methoxyphenyl)methyl]-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 

Downstream Products

• 102617-86-7 3,5-Dimethyl-2,4-dioxo-5-phenyl-imidazolidine-1-carbonitrile 
• 201607-11-6 (R)-3-methyl-5-methyl-5-phenylimidazolidine-2,4-dione 
• 201607-11-6 (R)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 
• 565-07-1 2-amino-2-phenylpropanoic acid 
• 4507-41-9 2-amino-2-phenyl propanoate de methyle 
• 1608154-38-6 3,5-dimethyl-5-phenyl-1-(5-(4-phenylpiperazin-1-yl)pentyl)imidazolidine-2,4-dione 
• 1608154-39-7 1-(5-(4-(2-fluorophenyl)piperazin-1-yl)pentyl)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 
• 1608154-40-0 1-(5-(4-(2-methoxyphenyl)piperazin-1-yl)pentyl)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 
• 1608154-32-0 C₁₆H₂₁BrN₂O₂ 

Relevant academic research and scientific papers

Connective synthesis of 5,5-disubstituted hydantoins by tandem α-amination and α-arylation of silyl ketene acetals

5,5-Disubstituted hydantoins, formally the cyclisation products of quaternary amino acids, were formed connectively from simple ester-derived starting materials by a one-pot tandem method. Amination of the silyl ketene acetal derivative of a methyl ester takes place by silver-catalysed addition to the N═N bond of an azocarboxamide, generating a N-amino-N′-aryl urea derivative of a substituted aminoester. Treatment with a base forms an ester enolate which undergoes arylation by intramolecular migration of an aryl ring to the α-position of the ester. The product undergoes ring closure to a hydantoin, which may itself be deprotected and functionalised. Aryl migration is successful with rings of various electronic character and with esters bearing functionalised and unfunctionalised chains, and the products have features in common with several bioactive compounds.

Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives

Available α-amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′-aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.

SAR-studies on the importance of aromatic ring topologies in search for selective 5-HT7 receptor ligands among phenylpiperazine hydantoin derivatives

The current study is focused on newly developed phenylpiperazine derivatives of aromatic methylhydantoin differing in mutual positions of methyl and phenyl moieties. The new compounds were synthesized using Bucherer-Bergs reaction, two-phase alkylation, Mitsunobu reaction and/or an alkylation under microwave irradiation. The compounds developed were assessed on their affinity for serotoninergic receptors 5-HT1A, 5-HT6, 5-HT 7 and α1-ARs in radioligand binding assays. Selected compounds were tested on their inhibitory effect at human 5-HT3A expressed in Xenopus Oocytes as well as on their activity at α1-adrenoceptor subtypes in functional and electrophysiological bioassays, respectively. Most of investigated compounds exhibited affinities for α1-ARs, 5-HT1A, 5-HT7 (Ki ～ 0.8-353 nM) significantly higher than those for 5-HT6 receptors. Very weak inhibitory effect at 5-HT3A accompanied with high activity at α1D-AR subtypes were observed for selected representative compounds. Among the current series, particularly 5-(4-fluorophenyl)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl) -5-methylimidazolidine-2,4-dione hydrochloride (25a) displayed the highest 5-HT7 affinity with Ki = 3 nM and selectivity with 40-3600 fold towards 5-HT1A, 5-HT6, and α1-ARs.

Intramolecular arylation of amino acid enolates

Dianionic enolates formed from N′-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N′-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway.

Racemic and Optically Active Hydantoins from Disubstituted Cyanoacetic Acids

Starting from the chiral disubstituted cyanoacetic acids 1 the racemates and some enantiomers of the 5,5-disubstituted hydantoins 6 and of the 3-methylhydantoins 7 are synthesized via the isocyanates 3.Their absolute configurations are determined.