3530-82-3Relevant articles and documents
Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions
Botla, Vinayak,Carfagna, Carla,Della Ca, Nicola,Gabriele, Bartolo,Maestri, Giovanni,Mancuso, Raffaella,Montanari, Luca,Motti, Elena,Voronov, Aleksandr
supporting information, p. 294 - 297 (2022/01/06)
The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.
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.
A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins
Vukeli?, Stella,Koksch, Beate,Seeberger, Peter H.,Gilmore, Kerry
, p. 13451 - 13454 (2016/09/13)
Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).
