Synthesis and antibacterial activity of 2,3‐dehydroofloxacin

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

Research output: Contribution to journalArticle

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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

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Ofloxacin
Oxazines
Fluorine
Quinolones
Aldehydes
Esters
Anti-Bacterial Agents
carbostyril

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Augeri, David ; Fray, Andrew H. ; Kleinman, Edward F. / Synthesis and antibacterial activity of 2,3‐dehydroofloxacin. In: Journal of Heterocyclic Chemistry. 1990 ; Vol. 27, No. 5. pp. 1509-1511.
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Synthesis and antibacterial activity of 2,3‐dehydroofloxacin. / Augeri, David; Fray, Andrew H.; Kleinman, Edward F.

In: Journal of Heterocyclic Chemistry, Vol. 27, No. 5, 01.01.1990, p. 1509-1511.

Research output: Contribution to journalArticle

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