70974-10-6

Usage

InChI:InChI=1/C11H12N2O2/c1-11(2)9(14)13(10(15)12-11)8-6-4-3-5-7-8/h3-7H,1-2H3,(H,12,15)

Upstream product

• 103-71-9 phenyl isocyanate 
• 19355-69-2 2-amino-2-cyanopropane 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 1483-73-4 diphenyliodonium bromide 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 66003-76-7 Diphenyliodonium triflate 
• 591-50-4 iodobenzene 
• 62-57-7 2-Aminoisobutyric acid 
• 98-80-6 phenylboronic acid 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 70974-09-3 5,5-dimethyl-3-(4-nitrophenyl)imidazolidine-2,4-dione 
• 87976-13-4 5,5-dimethyl-1,3-diphenyl imidazolidine-2,4-dione 
• 1394916-83-6 1-([1,1'-biphenyl]-4-yl)-5,5-dimethyl-3-phenylimidazolidine-2,4-dione 

Relevant academic research and scientific papers

N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature

Copper(I)-catalyzed N-arylation (both N1- and N3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts deliver

Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts

A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing elements. It is also applicable for the rapid diversification of pharmaceutically relevant hydantoins.

Copper-Mediated N-Arylations of Hydantoins

A set of two broadly applicable procedures for the N-arylation of hydantoins is reported. The first one relies on the use of stoichiometric copper(I) oxide under ligand- A nd base-free conditions and enables a clean regioselective arylation at the N3 nitrogen atom, while the second one is based on the use of catalytic copper(I) iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine and promotes arylation at the N1 nitrogen atom. Importantly, the combination of these two procedures affords a straightforward entry to diarylated hydantoins.

3,5,5-Trisubstituted hydantoins from activated (benzyloxycarbonylamino) malonic acids

Diethyl 2-alkyl-2-(benzyloxycarbonylamino)malonates were saponified, activated with oxalyl chloride, and treated with primary aromatic amines. This gave 3,5-disubstituted hydantoin-5-carboxamides. As second products, 2-alkyl-2-formamido-N1,Nsu

Comparison of copper(II) acetate promoted N-arylation of 5,5-dimethyl hydantoin and other imides with triarylbismuthanes and aryl boronic acids

This work demonstrates that the copper acetate promoted N-arylation of imides with boronic acids can be employed as a major method for the synthesis of N3-aryl hydantoins. Georg Thieme Verlag Stuttgart.

A large gem-dimethyl effect in the cyclization of ω-phenylhydantoic acids: Computational modeling of the gem-dimethyl effect on the acid- or base-catalyzed cyclization of hydantoic acids and esters

The rates of the cyclization of methyl-substituted 5-phenylhydantoic acids were measured in acid solutions. A particularly strong gem-dimethyl effect (GDME) was observed with the N-methyl compounds amounting to an acceleration of six powers of ten for the 2,2,3-trimethyl derivative. The variations in the free energies of activation for the cyclization of hydantoic acids and esters were modeled by the strain energies of the tetrahedral intermediates and of the reactants calculated by the MM3 force field. The neutral tetrahedral intermediate T0 was used for reaction series involving acid catalysis and the negatively charged intermediate T- for base catalysis. Very good agreement with the experimental GDME was obtained for the acid-catalyzed cyclizations of the complete series of the N-methyl-substituted substrates, showing that the accelerations result from a greater strain increase in the reactants. The results with T- are closely parallel, indicating that the loss of GDME observed under base catalysis with 2,2,3-trimethylhydantoate esters is not due to intramolecular strain in T-. A linear correlation (slope 1.22, r=0.934) is obtained for a plot of the free energy variations against strain energies for the reaction series of 5-phenylhydantoic acids when the data for the strongly deviating parent acid is excluded. Excellent LFERs are obtained between the reaction series of esters and acids. The observed large rate enhancements induced by N-substituents explain the switches to cyclization routes in synthetic reactions. Copyright