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4-Hydroxy-2-quinolones. 168*. Synthesis, chemical and antitubercular properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides

  • I. V. UkrainetsEmail author
  • L. A. Grinevich
  • A. A. Tkach
  • O. V. Bevz
  • S. V. Slobodzian
Article

1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather than in the amide part of the molecule. The 1-N-allyl derivative behaves similarly but undergoes halocyclization to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid pyrazin-2-ylamide. A comparative analysis of the antimycobacterial properties of the synthesized compounds and their isomeric pyrimidin-2-ylamides has been carried out.

Keywords

2-aminopyrazine 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides bromination antitubercular activity X-ray structural analysis 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • I. V. Ukrainets
    • 1
    Email author
  • L. A. Grinevich
    • 1
  • A. A. Tkach
    • 1
  • O. V. Bevz
    • 1
  • S. V. Slobodzian
    • 2
  1. 1.National University of PharmacyKharkivUkraine
  2. 2.Northern Michigan UniversityMarquetteUSA

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