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4-hydroxy-2-quinolones 165*. 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehydes and their thiosemicarbazones. Synthesis, structure, and biological properties

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Chemistry of Heterocyclic Compounds Aims and scope

Two variants are discussed of the synthesis of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid β-N-tosylhydrazides which undergo a McFayden-Stevens reaction to give 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehydes in high yields. It was shown that the thiosemicarbazones prepared from them exist in the solid state exclusively in the syn-form while in solution a hydrazone ↔ enhydrazine tautomerism is observed. The results of a study of the antitubercular activity of the synthesized compounds are reported.

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Authors and Affiliations

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

    I. V. Ukrainets, Liu Yangyang, A. A. Tkach & O. V. Gorokhova

  2. Taras Shevchenko National University, Kiev, 01033, Ukraine

    A. V. Turov

Authors
  1. I. V. Ukrainets
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  2. Liu Yangyang
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  3. A. A. Tkach
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  4. O. V. Gorokhova
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  5. A. V. Turov
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Corresponding author

Correspondence to I. V. Ukrainets.

Additional information

*For Communication 164 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 883–894, June, 2009.

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Ukrainets, I.V., Yangyang, L., Tkach, A.A. et al. 4-hydroxy-2-quinolones 165*. 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehydes and their thiosemicarbazones. Synthesis, structure, and biological properties. Chem Heterocycl Comp 45, 705–714 (2009). https://doi.org/10.1007/s10593-009-0327-2

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  • DOI: https://doi.org/10.1007/s10593-009-0327-2

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