… condensed β-lactams-I: The application of diketene in β-lactam synthesis. The synthesis and functional group manipulations of diethyl 3-acetyl-4-oxoazetidine-2, 2- …

G Simig, G Doleschall, G Hornyák, J Fetter, K Lempert…

Index: Simig, Gyula; Doleschall, Gabor; Hornyak, Gyula; Fetter, Jozsef; Lempert, Karoly; et al. Tetrahedron, 1985 , vol. 41, # 2 p. 479 - 484

Full Text: HTML

Citation Number: 20

Abstract

Acylation of the N-substituted diethyl aminomalonates 3a–3d with diketene furnished the ring tautomers 6a–6d of the expected acetoacetyl derivatives 5. By treatment with iodine and sodium ethoxide compounds 6a–6d are smoothly converted into the β-lactam derivatives 2a– 2d. Deethoxycarbonylation of the ethylene ketals 7a–7d of the latter furnishes mixtures of the corresponding diastereomeric monoesters 8 and10. The ethoxycarbonyl groups of the ...