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Transformation of a spirobarbituric acid via aminobarbituric acid‐hydantoin rearrangement
Author(s) -
Ambrożak Agnieszka,
Güutschow Michael
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430346
Subject(s) - chemistry , hydantoin , sodium ethoxide , bicyclic molecule , decane , imidazole , pyrrolidine , stereochemistry , medicinal chemistry , organic chemistry , ethanol
A successful application of the aminobarbituric acid‐hydantoin rearrangement to produce a bicyclic carbamoylhydantoin from an intermediate spirobarbituric acid is reported. 7a‐Phenylcarbamoyl‐tetrahydro‐1 H ‐pyrrolo[1,2‐ c ]imidazole‐1,3(2 H )‐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.