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Synthesis 2011(1): 69-72  
DOI: 10.1055/s-0030-1258966
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Step Synthesis of β-Lactams with Retro-Amide Side Chain

Karolina Janikowska, Natalia Pawelska, Sławomir Makowiec*
Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-952 Gdansk, Poland
Fax: +48(58)3472694; e-Mail: mak@chem.pg.gda.pl;
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Publication History

Received 6 September 2010
Publication Date:
09 November 2010 (online)

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Abstract

A one-pot synthesis for the preparation of 1,4-disubstituted 2-oxoazetidine-3-carboxylic acid amides was developed. 5-[(N-substituted-amino)(hydroxy)methylene] Meldrum’s acids act as a source of ketenes that react with aldimines in boiling toluene to give β-lactams with a retro-amide side chain.

Key words

lactams - cycloaddition - amides - ketenes - Meldrum’s acid

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