A New One-Pot Synthesis of 5,5-Disubstituted Hydantoins from Diethyl Acetamidomalonates and Ureas

Michael Gütschow; Thomas Hecker; Kurt Eger

doi:10.1055/s-1999-3413

Synthesis 1999; 1999(3): 410-414
DOI: 10.1055/s-1999-3413

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A New One-Pot Synthesis of 5,5-Disubstituted Hydantoins from Diethyl Acetamidomalonates and Ureas

Michael Gütschow^* , Thomas Hecker, Kurt Eger

^*Institut für Pharmazie - Pharmazeutische Chemie - der Universität Leipzig, Brüderstraße 34, D-04103 Leipzig, Germany; Fax +49(3 41)9 73 67 49; E-mail: guetscho@uni-leipzig.de

Abstract

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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 3a-e. The reaction involves a ring contraction of intermediate 5-aminobarbituric acids to the final hydantoin derivatives. The 5-aminobarbituric acids 2d-f were prepared from azido derivatives 6d-f. On treatment with sodium ethoxide, 2d-f underwent the rearrangement to afford the hydantoins 3d-f.

5-aminobarbituric acids - hydantoins - ring contraction - diethyl acetamidomalonates - ureas

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