Abstract
Abstractmagnified imageA successful application of the aminobarbituric acid‐hydantoin rearrangement to produce a bicyclic carbamoylhydantoin from an intermediate spirobarbituric acid is reported. 7a‐Phenylcarbamoyl‐tetrahydro‐1H‐pyrrolo[1,2‐c]imidazole‐1,3(2H)‐dione (8) was obtained in a one‐pot multistep reaction of 1‐acetyl‐2,2‐bis(ethoxycarbonyl)pyrrolidine (5) and phenylurea in the presence of sodium ethoxide. Under less severe conditions, 5 and phenylurea were reacted to afford 1‐acetyl‐7‐phenyl‐triaza[4,5]decane‐6,8,10‐trione (6). The structural elucidation of the bicyclic hydantoin 8 and the spirobarbituric acid 6 was based on relevant nmr signals in accordance with those of reference compounds, i.e. monocyclic hydantoins 4a,b and acetamidobarbituric acids 2a‐c. The latter compounds were newly prepared from diethyl acetamidomalonates 1 and phenylurea.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
