An alternative synthesis of temafloxacin, a potent antibacterial agent

Authors:
  • DCDaniel T. W. Chu
    Daniel T. W. Chu
  • ILIsabella M. Lico
    Isabella M. Lico
  • ACAkiyo K. Claiborne
    Akiyo K. Claiborne
  • HFHermann Faubl
    Hermann Faubl
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Abstract
An alternative synthesis of (±)-7-(3-methylpiperazin-1-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride 4, a potent antibacterial agent, was developed. The method was characterized by regiospecific displacement of the 4-fluoro of the 2,4,5-trifluoroacetophenone by 2-methylpiperazine to produce the key intermediate, 2,5-difluoro-4-(3-methylpiperazin-1-yl)acetophenone 12, which was subsequently converted to 4 via an intramolecular nucleophilic displacement cyclization reaction.