Simple and 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-dicarboxylates

Gyula Simig, Gábor Doleschall, Gyula Hornyák, József Fetter, Károly Lempert, József Nyitrai, Péter Huszthy, Tibor Gizur, Mária Kajtár-Peredy

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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 trans esters 8 are more reactive than those of the cis isomers 10. This permits, under appropriate conditions, selective alkaline hydrolysis and NaBH4 reduction of the trans esters 8 in the presence of the cis esters 10. Reduction of the cis ester 10c under more forceful conditions furnishes the trans hydroxymethyl derivative 11c.

Original languageEnglish
Pages (from-to)479-484
Number of pages6
JournalTetrahedron
Volume41
Issue number2
DOIs
Publication statusPublished - 1985

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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