221679-72-7Relevant academic research and scientific papers
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.
