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One step access to oxindole-based β-lactams through Ugi four-center three-component reaction.

ABSTRACT: A multicomponent Ugi reaction involving isatin, isocyanide and β-amino acid components has been developed. The reactions proceeded smoothly to give β-lactam-containing 3,3-disubstituted oxindoles in only one step and generally high yields. When chiral, non racemic, β-amino acids were used, products were obtained as enantiomerically pure β-lactams diastereoisomers, whose relative stereochemistry was determined by X-ray analysis. For one compound, a weak antibacterial activity has been preliminarily highlighted.

SUBMITTER: Rainoldi G

PROVIDER: S-EPMC9087354 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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One step access to oxindole-based β-lactams through Ugi four-center three-component reaction.

Rainoldi Giulia G Lesma Giordano G Picozzi Claudia C Lo Presti Leonardo L Silvani Alessandra A

RSC advances 20181011 61

A multicomponent Ugi reaction involving isatin, isocyanide and β-amino acid components has been developed. The reactions proceeded smoothly to give β-lactam-containing 3,3-disubstituted oxindoles in only one step and generally high yields. When chiral, non racemic, β-amino acids were used, products were obtained as enantiomerically pure β-lactams diastereoisomers, whose relative stereochemistry was determined by X-ray analysis. For one compound, a weak antibacterial activity has been preliminari ...[more]

PMID: 35547060

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