33558-00-8Relevant academic research and scientific papers
Syntheses based on natural α-amino acids. Cyanoethylation of 3-substituted 5-methyl-2-thiohydantoins
Ayupova,Shakhidoyatov
, p. 1394 - 1397 (2005)
Starting from α-alanine, the C- and S-cyanoethyl derivatives of 5-methyl-3-phenyl(allyl)-2-thiohydantoins have been synthesized. It was shown that the products of hydrolysis of C-cyanoethyl derivatives, 5-methyl-3-phenyl(allyl)-(β-carboxyethyl)-2-thiohydantoins, are formed in addition. 2005 Springer Science+Business Media, Inc.
Photochemical Deracemization at sp3-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer
Bach, Thorsten,Breitenlechner, Stefan,Gro?kopf, Johannes,Plaza, Manuel,Seitz, Antonia,Storch, Golo
supporting information, p. 21241 - 21245 (2021/12/27)
A photochemical deracemization of 5-substituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80–99% ee). The reaction is catalyzed by a chiral diarylketone which displays a two-point hydrogen bonding site. Mechanistic evidence (DFT calculations, radical clock experiments, H/D labeling) suggests the reaction to occur by selective hydrogen atom transfer (HAT). Upon hydrogen binding, one substrate enantiomer displays the hydrogen atom at the stereogenic center to the photoexcited catalyst allowing for a HAT from the substrate and eventually for its conversion into the product enantiomer. The product enantiomer is not processed by the catalyst and is thus enriched in the photostationary state.
N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature
Abha Saikia, Raktim,Barman, Dhiraj,Dutta, Anurag,Jyoti Thakur, Ashim
, p. 400 - 410 (2020/12/17)
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
Neerbye Berntsen, Linn,Nova, Ainara,Wragg, David S.,Sandtorv, Alexander H.
, p. 2687 - 2691 (2020/04/10)
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
Thilmany, Pierre,Gérard, Phidéline,Vanoost, Agathe,Deldaele, Christopher,Petit, Laurent,Evano, Gwilherm
, p. 392 - 400 (2018/12/11)
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.
Microwave-assisted solid-phase synthesis of hydantoin derivatives
Colacino, Evelina,Lamaty, Frédéric,Martinez, Jean,Parrot, Isabelle
, p. 5317 - 5320 (2008/02/09)
A microwave-assisted synthesis of 3,5- and 1,3,5-substituted hydantoins starting from various resins for solid-phase combinatorial chemistry has been developed. The hydantoins were synthesized from pre-loaded resins with amino acids via treatment with isocyanate or phenylisocyanate and subsequent intramolecular cyclization. Both reactions were performed under microwave irradiation. We studied the cyclative cleavage leading to hydantoin compounds dependent on the nature of the amino acid and the nucleofuge properties of the resin.
BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID
Kavalek, Jaromir,Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
, p. 375 - 390 (2007/10/02)
Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.
SUBSTITUENT EFFECTS ON HYDROLYTIC STABILITY AND HERBICIDAL ACTIVITY OF 3-ARYLIMIDAZOLIDINE-2,4-DIONES
Cegan, Alexandr,Vecera, Miroslav
, p. 1521 - 1528 (2007/10/02)
Twenty-one derivatives of imidazolidine-2,4-dione have been prepared by reactions of substituted amino acids with aryl isocyanates in aqueous medium.Pre- and post-emergent herbicidal activities of all the compounds have been tested, and stability of five derivatives has been followed in aqueous medium within the pH range from 7.6 to 13.0.The highest pre-emergent herbicidal activity has been found with the derivatives XI-XVI which inhibit the growth of most indicator plants at the doses of 1.6 kg/ha.The derivatives studied are relatively stable in aqueous medium, the hydrolysis half-life of the compound XI being 9 days at pH 8.
SYNTHESIS AND NITROSATION OF 3- AND 3,5-SUBSTITUTED HYDANTOINS
Klimavichyus, K.-A. V.,Lutsenko, V. V.,Paulauskaite, G. V.,Mikul'skis, P. P.,Bal'chitis, G. A.,Ionushauskas, S. L.
, p. 1160 - 1162 (2007/10/02)
The cyclization of N-alkylated(arylated) α-ureidocarboxylic acids gives a series of 3-mono- and 3,5-disubstituted hydantoins, and nitrosation of the latter yields their nitroso derivatives.The rotational isomerism of 3-(α-naphthyl)hydantoins has been stud
