4-HYDROXY-2-QUINOLONES. 165. 1-R-4-HYDROXY-2-OXO-1,2-DIHYDROQUINOLINE-3-CARBALDEHYDES AND THEIR THIOSEMICARBAZONES. SYNTHESIS, STRUCTURE, AND BIOLOGICAL PROPERTIES

Authors

  • И. В. Украинец National University of Pharmacy, Kharkiv 61002
  • Лю Янян National University of Pharmacy, Kharkiv 61002
  • А. А. Ткач National University of Pharmacy, Kharkiv 61002
  • О. В. Горохова National University of Pharmacy, Kharkiv 61002
  • А. В. Туров Taras Shevchenko National University, Kiev 01033

DOI:

https://doi.org/10.1007/6694

Keywords:

4-hydroxy-2-oxo-1, 2-dihydroquinoline-3-carbaldehydes, thiosemicarbazones, isomerization, antitubercular activity, X-ray structural analysis

Abstract

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.

How to Cite
Ukrainets, I. V.; Yangyang, L.; Tkach, A. A.; Gorokhova, O. V.; Turov, A. V.  Chem. Heterocycl. Compd. 2009, 45, 705. [Khim. Geterotsikl. Soedin. 2009, 883.]

For this article in the English edition see DOI 10.1007/s10593-009-0327-2

 

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Published

2022-03-24

Issue

No. 6 (2009)

Section

Original Papers