Simple and condensed β-lactams. Part 32. Base- and acid-catalyzed ring expansions of 3-substituted 4-acetylazetidin-2-ones and related compounds

Attila Sápi, J. Fetter, Károly Lempert, M. Kajtár-Peredy, Gábor Czira

Research output: Contribution to journalArticle

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Abstract

On treatment with bases, the C3-C4 bonds of the 3-substituted 4-(1-iminoethyl)-or 4-acetylazetidin-2-ones 8f, 8g and 8i are cleaved heterolytically to afford, depending on the nature of the 3-substituent, ring expansion or other products (14, 19 and 27, respectively). Related compound 8h undergoes a base-induced ring transformation to afford compound 23 only after oxidation to the stereoisomeric disulfanes 20. Compound 8d, when treated with HCl, undergoes a ring transformation to pyrrolidin-2-one 32.

Original languageEnglish
Pages (from-to)190-202
Number of pages13
JournalCollection of Czechoslovak Chemical Communications
Volume64
Issue number2
Publication statusPublished - 1999

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Lactams
Oxidation
Acids

Keywords

  • β-Lactams
  • Azetidin-2-ones
  • Pyrazines
  • Ring transformations

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "On treatment with bases, the C3-C4 bonds of the 3-substituted 4-(1-iminoethyl)-or 4-acetylazetidin-2-ones 8f, 8g and 8i are cleaved heterolytically to afford, depending on the nature of the 3-substituent, ring expansion or other products (14, 19 and 27, respectively). Related compound 8h undergoes a base-induced ring transformation to afford compound 23 only after oxidation to the stereoisomeric disulfanes 20. Compound 8d, when treated with HCl, undergoes a ring transformation to pyrrolidin-2-one 32.",
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T1 - Simple and condensed β-lactams. Part 32. Base- and acid-catalyzed ring expansions of 3-substituted 4-acetylazetidin-2-ones and related compounds

AU - Sápi, Attila

AU - Fetter, J.

AU - Lempert, Károly

AU - Kajtár-Peredy, M.

AU - Czira, Gábor

PY - 1999

Y1 - 1999

N2 - On treatment with bases, the C3-C4 bonds of the 3-substituted 4-(1-iminoethyl)-or 4-acetylazetidin-2-ones 8f, 8g and 8i are cleaved heterolytically to afford, depending on the nature of the 3-substituent, ring expansion or other products (14, 19 and 27, respectively). Related compound 8h undergoes a base-induced ring transformation to afford compound 23 only after oxidation to the stereoisomeric disulfanes 20. Compound 8d, when treated with HCl, undergoes a ring transformation to pyrrolidin-2-one 32.

AB - On treatment with bases, the C3-C4 bonds of the 3-substituted 4-(1-iminoethyl)-or 4-acetylazetidin-2-ones 8f, 8g and 8i are cleaved heterolytically to afford, depending on the nature of the 3-substituent, ring expansion or other products (14, 19 and 27, respectively). Related compound 8h undergoes a base-induced ring transformation to afford compound 23 only after oxidation to the stereoisomeric disulfanes 20. Compound 8d, when treated with HCl, undergoes a ring transformation to pyrrolidin-2-one 32.

KW - β-Lactams

KW - Azetidin-2-ones

KW - Pyrazines

KW - Ring transformations

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