Simple and condensed β-lactams. Part 29. Synthesis and base-catalyzed ring transformation of 4-[(2RS,3SR)-3-hydroxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl)]thiazol-2(3H) -one

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

4-[(2RS,3RS)-3-Hydroxy- (1b) and -3-(4-chlorophenoxy)-1-(4-methoxyphenyl)-4-oxo azetidin-2-yl]thiazol-2(3H)-one (16b) were synthesised. While the former was smoothly rearranged into (5RS)-5-hydroxy-7-(4-methoxyphenyl)-1,5-dihydrothiazolo[3,4-a]pyrazine-3,6(7H) -dione (7b) on treatment with Na2CO3 under mild conditions, the latter was found to be stable to Na2CO3 under the same conditions. The structural prerequisites for type 1 → 7 ring transformations, including cleavage of the 3-4 bond (azetidin-2-one numbering) of the β-lactam ring are defined.

Original languageEnglish
Pages (from-to)12729-12738
Number of pages10
JournalTetrahedron
Volume53
Issue number37
DOIs
Publication statusPublished - Sep 1997

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Pyrazines
Lactams

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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Simple and condensed β-lactams. Part 29. Synthesis and base-catalyzed ring transformation of 4-[(2RS,3SR)-3-hydroxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl)]thiazol-2(3H) -one. / Sápi, Attila; Fetter, J.; Lempert, Károly; Kajtár-Peredy, M.; Czira, Gábor.

In: Tetrahedron, Vol. 53, No. 37, 09.1997, p. 12729-12738.

Research output: Contribution to journalArticle

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