Synthesis and antibacterial activity of 2,3‐dehydroofloxacin

David J. Augeri, Andrew H. Fray, Edward F. Kleinman

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

The 2,3‐dehydro analog 2 of the potent quinolone antibacterial agent ofloxacin (1) was synthesized by an efficient six step route beginning with ethyl 2,3,4,5‐tetrafluorobenzoylacetate. Formation of the oxazine ring of 2 was accomplished by ozonolysis of 1‐(1‐buten‐3‐yl)quinolone 5 to the corresponding aldehyde, which cyclized upon treatment with base via intramolecular displacement of the C‐8 fluorine to afford tricyclic ester 6. The antibacterial activities of 2,3‐dehydroofloxacin (2) and ofloxacin (1) are compared.

Original languageEnglish (US)
Pages (from-to)1509-1511
Number of pages3
JournalJournal of Heterocyclic Chemistry
Volume27
Issue number5
DOIs
StatePublished - Jan 1 1990
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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