133384-65-3

Upstream product

• 3530-82-3 5-benzyl-hydantoin 
• 555-16-8 4-nitrobenzaldehdye 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 2295-31-0 thiazoline-2,4-dione 
• 461-72-3 2,4-imidazolidinedione 

Downstream Products

• 116705-22-7 5-(4'-nitrobenzylidene)-hydantoin 

Relevant academic research and scientific papers

Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies

Benzoxazolyl linked meta- and para-substituted new chemical entities (5a–5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectra

Hydantoin-based molecular photoswitches

A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level.

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

Diethyl 2,4-Dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons Reagents for the Mild and Efficient Preparation of C-5 Unsaturated Hydantoin Derivatives

The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite.The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield.The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate.The isomeric configuration of the products was determined from analysis of NMR spectral data.Long-range (13)C-(1)H coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry.Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and α-dicarbonyl compounds to afford the corresponding olefinic products.C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to α-amino acid derivatives, pyruvates, and the imidazoquinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.

Latent Inhibitors. Part 6. Inhibition of Dihydro-orotate Dehydrogenase by Substituted 5-Benzylhydantoins

A series of substituted 5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoins was prepared by condensation of aromatic aldehydes with the corresponding 5-unsubstituted hydantoin followed by reduction of the intermediate benzylidene derivative.The compounds were