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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.