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, J. Fetter, Károly Lempert, József Nyitrai, P. Huszthy, Tibor Gizur, M. 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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Lactams
Functional groups
Esters
Derivatives
Sodium Compounds
Sodium compounds
Acylation
Iodine
Isomers
Hydrolysis
diketene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Simig, Gyula; Doleschall, Gábor; Hornyák, Gyula; Fetter, J.; Lempert, Károly; Nyitrai, József; Huszthy, P.; Gizur, Tibor; Kajtár-Peredy, M.

In: Tetrahedron, Vol. 41, No. 2, 1985, p. 479-484.

Research output: Contribution to journalArticle

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AU - Doleschall, Gábor

AU - Hornyák, Gyula

AU - Fetter, J.

AU - Lempert, Károly

AU - Nyitrai, József

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AU - Gizur, Tibor

AU - Kajtár-Peredy, M.

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AB - 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.

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