Simple and condensed β‐lactams, XIX. Synthesis Of some new 7‐acylamino‐2‐iso‐oxacephem‐4‐carboxylic acids

Zoltán Tombor, Zoltán Greff, József Nyitrai, M. Kajtár-Peredy

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

General methods have been developed for the synthesis of 7‐amino‐2‐iso‐oxacephem‐4‐carboxylic acid esters 21a,b; 35b. Clayfen [Fe(III) nitrate supported by montmorillonite] was used for the preparation of benzyl 2,3‐dioxobutyrate (3). The latter readily reacted with N(1)‐unsubstituted β‐lactams (9a, 28) to give products formed by addition reaction on the middle carbonyl‐C atom. These intermediates furnished the corresponding acetoacetic esters 10, 29 which gave by ring closure the O‐mono‐ and the O,N‐diprotected‐2‐iso‐oxacephems (11, 30). Intermolecular carbene insertion was used for the synthesis of tert‐butyl 2‐(2‐oxoazetidin‐1‐yl)acetoacetates 19a,b whose ring closure led to the tert‐butyl 2‐iso‐oxa‐cephem‐4‐carboxylates 20a,b. The O‐protecting tert‐butyl group could be removed without decomposition of the 2‐isooxacephem moiety to give 2‐iso‐oxacephem‐4‐carboxylic acids 2a,b which exhibit antibacterial activity against Grampositive microorganisms.

Original languageEnglish
Pages (from-to)825-835
Number of pages11
JournalLiebigs Annalen
Volume1995
Issue number5
DOIs
Publication statusPublished - Apr 24 1995

Fingerprint

Lactams
Acetoacetates
closures
esters
Esters
Bentonite
Addition reactions
acids
Acids
rings
carbenes
microorganisms
synthesis
montmorillonite
Microorganisms
Nitrates
nitrates
insertion
Decomposition
decomposition

Keywords

  • 2‐Iso‐oxacephems
  • Antibacterial activity
  • Benzyl 2,3‐dioxobutyrate

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Simple and condensed β‐lactams, XIX. Synthesis Of some new 7‐acylamino‐2‐iso‐oxacephem‐4‐carboxylic acids. / Tombor, Zoltán; Greff, Zoltán; Nyitrai, József; Kajtár-Peredy, M.

In: Liebigs Annalen, Vol. 1995, No. 5, 24.04.1995, p. 825-835.

Research output: Contribution to journalArticle

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