7684-19-7Relevant articles and documents
Synthesis of Chiral Hydantoins and Thiazolidinediones via Iridium-Catalyzed Asymmetric Hydrogenation
Li, Jing,Nie, Yu,Yuan, Qianjia,Zhang, Wanbin
supporting information, (2022/01/31)
Herein, we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand. The transformation shows good functional group tolerance, and gives the hydrogenated pro
Substituted 2-thioxoimidazolidin-4-ones and imidazolidine-2,4-diones as fatty acid amide hydrolase inhibitors templates
Muccioli, Giulio G.,Fazio, Nicola,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Cannata, Fabio,Poupaert, Jacques H.,Wouters, Johan,Lambert, Didier M.
, p. 417 - 425 (2007/10/03)
The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and 2-thioxoimidazolidin-4-one derivatives was evaluated as FAAH inhibitors. Among these compounds, 3-substituted 5,5′-diphenylimidazolidine-2,4-dione and 3-substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one derivatives were previously described as CB1 cannabinoid receptor ligands. In the present study, we synthesized several derivatives exhibiting interesting FAAH inhibitory activity and devoid of affinity for the CB1 and CB2 cannabinoid receptors. For instance, 3-heptyl-5,5′-diphenylimidazolidine- 2,4-dione (14) and 5,5′-diphenyl-3-tetradecyl-2-thioxo-imidazolidin-4-one (46) showed p/50 values of 5.12 and 5.94, respectively. In conclusion, it appears that even though several 3-substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one and 3-substituted 5,5′-diphenylimidazolidine-2,4-dione derivatives have been previously shown to behave as CB1 cannabinoid receptor ligands, appropriate substitutions of these templates can result in FAAH inhibitors devoid of affinity for the cannabinoid receptors.
New one-pot three-component synthesis of N-phenyl α-aminophosphonates
Deng, Sheng-Lou,Dong, He-Chao
, p. 3411 - 3417 (2007/10/03)
New one-pot three-component reactions employing aldehydes, triphenylphosphite, and N-[(phenylamino)carbonyl]glycine ethyl ester in refluxing xylene readily afford N-phenyl α-aminophosphonates in low to moderate yields. Copyright Taylor & Francis Group, LL
N-H insertion reactions of primary ureas: The synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls
Lee, Sang-Hyeup,Yoshida, Kazuhiro,Matsushita, Hana,Clapham, Bruce,Koch, Guido,Zimmermann, Juerg,Janda, Kim D.
, p. 8829 - 8835 (2007/10/03)
Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoket
A New Method of Synthesis of 3-Monosubstituted-2-thiohydantoins and -Hydantoins
Ryczek, J.
, p. 2599 - 2604 (2007/10/02)
A new method of synthesis of 3-monosubstituted derivatives of 2-thiohydantoin and hydantoin in reaction of isothiocyanate or isocyanate glycin ethyl ester with primary aliphatic and aromatic amines has been described. Crude products were obtained with high yield and purity. The structure of these compounds was confirmed by spectral methods. Key words: 2-thiohydantoin, hydantoin, isothiocyanate glycin ethyl ester, isocyanate glycin ethyl ester
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.
Process for preparing substituted urea derivatives
-
, (2008/06/13)
A process for the preparation of substituted urea derivatives, and compositions and concentrates for the same purpose are disclosed. According to the process the substituted urea derivatives of formula (I) STR1 wherein R is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R1 and R2 are hydrogen, alkyl, alkenyl, alkinyl, alkoxy, oxyalkyl, cycloalkyl, aralkyl, alkoxycarbonylalkyl, aryl or heteroaryl, or R1 and R2 together with the adjacent nitrogen atom may form a saturated or unsaturated heterocycle, or a condensed and/or substituted ring system, and said heterocycle or said condensed and/or substituted ring system may contain also a sulfo group, can be manufactured by reacting an amine of formula (II) STR2 with an N-carbamoyl-benzoic acid sulfimide derivative of formula (III) STR3 The disclosed N-acylating composition comprises of from 3 to 60% by weight, preferably of from 5 to 50% by weight sulfimide derivative of formula (III), of from 97 to 40% by weight, preferably of from 95 to 50% by weight solvent, and if desired, an organic or inorganic base. The disclosed N-acylating concentrate comprises of from 60 to 95.5% by weight N-acylating agent of formula (III) and of from 4.5 to 40% by weight additives.
