A 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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.