Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides |
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Authors: | Colin L Gibson Alan R Kennedy Raghavendar R Morthala John A Parkinson Colin J Suckling |
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Institution: | Department of Pure and Applied Chemistry, 295 Cathedral Street, University of Strathclyde, Glasgow G1 1XL, UK |
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Abstract: | Reactions of N-protected derivatives of Weinreb amides of alanine with strong base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form an imidazolidinone. |
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