34658-65-6Relevant articles and documents
Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh
supporting information, p. 2285 - 2290 (2017/10/06)
A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.
Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: Byproduct-free prenylation of hydantoins
Schmitt, Daniel C.,Lee, Jungyong,Dechert-Schmitt, Anne-Marie R.,Yamaguchi, Eiji,Krische, Michael J.
, p. 6096 - 6098 (2013/07/11)
The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2) 2] promotes the direct C-C coupling of isoprene with aryl substituted hydantoins 1a-1f at the diene C4-position to furnish products of n-prenylation 2a-2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative coupling to furnish a transient aza-ruthencyclopentene is proposed.
Functionalized amino acid anticonvulsants: Synthesis and pharmacological evaluation of conformationally restricted analogues
LeTiran,Stables,Kohn
, p. 2693 - 2708 (2007/10/03)
Proven conformationally restricted analogues of anticonvulsant functionalized amino acids (FAAs) were prepared using short-range cyclizations and evaluated in pharmacological assays providing new information concerning the structural requirements for FAA function.
Palladium-catalyzed synthesis of substituted hydantoins - A new carbonylation reaction for the synthesis of amino acid derivatives
Beller, Matthias,Eckert, Markus,Moradi, Wahed A.,Neumann, Helfried
, p. 1454 - 1457 (2007/10/03)
One-step synthesis of substituted hydantoins can be achieved by the palladium-catalyzed 'ureidocarbonylation' of aldehydes with urea derivatives and carbon monoxide [Eq. (1)]. This surprisingly selective protocol converts substituted ureas into 1,5- and 1,3,5-substituted hydantoins in yields of up to 93 %.