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The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs.

Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides

Gibson, Colin and Kennedy, A.R. and Morthala, R.R. and Parkinson, J.A. and Suckling, C.J. (2008) Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides. Tetrahedron, 64 (32). pp. 7619-7625. ISSN 0040-4020

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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.