Synthesis and antibacterial activity of 2,3‐dehydroofloxacin | Zendy

Augeri David J. | Zendy; Fray Andrew H. | Zendy; Kleinman Edward F. | Zendy

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Synthesis and antibacterial activity of 2,3‐dehydroofloxacin

Author(s) -

Augeri David J.,

Fray Andrew H.,

Kleinman Edward F.

Publication year - 1990

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570270561

Subject(s) - chemistry , ofloxacin , quinolone , intramolecular force , antibacterial activity , ozonolysis , tricyclic , aldehyde , ring (chemistry) , stereochemistry , antibacterial agent , combinatorial chemistry , organic chemistry , antibiotics , bacteria , catalysis , biochemistry , ciprofloxacin , biology , genetics

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.

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