569336-75-0Relevant academic research and scientific papers
The aminobarbituric acid-hydantoin rearrangement
Meusel, Manuela,Ambrozak, Agnieszka,Hecker, Thomas K.,Guetschow, Michael
, p. 4684 - 4692 (2007/10/03)
A general synthesis protocol for the generation of tri- and tetrasubstituted 5-carbamoylhydantoins is described. Starting from barbituric acids and following bromination and reaction with primary amines, 5-aminobarbituric acids 3a-s and 8 were prepared. C
A new one-pot synthesis of 5,5-disubstituted hydantoins from diethyl acetamidomalonates and ureas
Guetschow, Michael,Hecker, Thomas,Eger, Kurt
, p. 410 - 414 (2007/10/03)
A new one-pot synthesis of 5,5-disubstituted hydantoins 3 is reported. Diethyl 2-acetamido-2-alkylmalonates were found to react with substituted ureas in the presence of sodium ethoxide to produce the 5-alkyl-5- carbamoylhydantoins 3 a-e. The reaction involves a ring contraction of intermediate 5-aminobarbituric acids to the final hydantoin derivatives. The 5-aminobarbituric acids 2 d-f were prepared from azido derivatives 6 d-f. On treatment with sodium ethoxide, 2 d-f underwent the rearrangement to afford the hydantoins 3 d-f.
