Tetrahedron

A direct link between the Passerini reaction and α-lactams

I Lengyel, V Cesare, T Taldone

Index: Lengyel, Istvan; Cesare, Victor; Taldone, Tony Tetrahedron, 2004 , vol. 60, # 5 p. 1107 - 1124

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Citation Number: 11

Abstract

α-Lactams (aziridinones) can function to replace two of the three reactants, the oxo- compound and the isonitrile, in the Passerini reaction. Four α-lactams () were reacted with mono-and dicarboxylic acids of positive pKa values to give 2-acyloxycarboxamides () and bis-2-acyloxycarboxamide products and, respectively. The same compounds were also prepared via the Passerini reaction. Acids with a negative pKa decarbonylate α-lactams to ...