40856-76-6Relevant academic research and scientific papers
Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin
Konnert, Laure,Reneaud, Benjamin,De Figueiredo, Renata Marcia,Campagne, Jean-Marc,Lamaty, Frdric,Martinez, Jean,Colacino, Evelina
, p. 10132 - 10142 (2015/02/19)
The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.
Dibutylphosphate (DBP) mediated synthesis of cyclic N,N′- disubstituted urea derivatives from amino esters: A comparative study
Agrawal, Sumit K.,Sathe, Manisha,Kaushik, M. P.,Halve, A. K.
, p. 5996 - 5999,4 (2020/08/20)
The N,N′-disubstituted urea derivatives such as amino acid hydantoins and dihydrouracil derivatives were prepared starting from natural and unnatural amino acid esters using dibutylphosphate (DBP). During the attempted synthesis of N-heterocycles with larger than six-membered rings containing the N,N′-disubstituted urea functionalities, three unexpected products namely squamolone, N-methyl pyrrolidine-2-one, and diketopiperazine were isolated.
Synthesis of 1S,5R- and 1R,5S-glycoluriles by diastereospecific α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one
Chikunov, Il'ya E.,Kravchenko, Angelina N.,Belyakov, Pavel A.,Lyssenko, Konstantin A.,Baranov, Vladimir V.,Lebedev, Oleg V.,Makhova, Nina N.
, p. 253 - 255 (2007/10/03)
A diastereospecific method for the synthesis of individual enantiomers of 1S,5R- and 1R,5S-glycoluriles has been developed based on the α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one.
