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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. National University of Pharmacy, Kharkiv, 61002, Ukraine

    I. V. Ukrainets, L. A. Grinevich, A. A. Tkach & O. V. Bevz

  2. Northern Michigan University, Marquette, 49855, Michigan, USA

    S. V. Slobodzian

Authors
  1. I. V. Ukrainets
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  2. L. A. Grinevich
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  3. A. A. Tkach
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  4. O. V. Bevz
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  5. S. V. Slobodzian
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Correspondence to I. V. Ukrainets.

Additional information

*For Communication 167 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1324–1337, September, 2009.

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Ukrainets, I.V., Grinevich, L.A., Tkach, A.A. et al. 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. Chem Heterocycl Comp 45, 1058–1068 (2009). https://doi.org/10.1007/s10593-009-0384-6

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  • DOI: https://doi.org/10.1007/s10593-009-0384-6

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