Home Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester
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Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester

  • Mustafa M. El-Abadelah EMAIL logo , Mohammed M. Abadleh , Firas F. Awwadi , Salim S. Sabri and Wolfgang Voelter EMAIL logo
Published/Copyright: December 9, 2017
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 73 Issue 1

Abstract

Direct interaction of dithizone with 7-chloro-6- fluoro-8-nitro-4-oxoquinoline-3-carboxylic acid or with its ester delivered the corresponding novel 1,3,4-thiadiazino [5,6-h]quinoline 3-carboxylic acid, or its ester which was then hydrolyzed to the respective acid. Structures of the latter tricyclic hybrids were deduced from analytical and spectral data and confirmed by single crystal X-ray structure determination of the ester derivative. The free acid showed moderate activity against Staphylococcus aureus with a MIC value of 25 μg mL−1.

Keywords: 7-chloro-8-nitroquinolone; antibacterial activity; dithizone; Smiles rearrangement; X-ray structure determination

Acknowledgments

We wish to thank the Deanship of Scientific Research at The University of Jordan, Amman, Jordan, for financial support.

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Supplemental Material:

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2017-0136).

Received: 2017-8-3
Accepted: 2017-10-15
Published Online: 2017-12-9
Published in Print: 2018-1-26

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. Obituary
  4. Gérard Demazeau, 07.06.1943–03.11.2017
  5. Synthesis and reactivity of β-stannylated phenylalanines
  6. Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile promoted by amino-functionalized CoFe2O4@SiO2 nanoparticles under conventional heating, microwave and ultrasound irradiations
  7. Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester
  8. No solid solution compounds in between the binaries: syntheses and crystal structures of Nb(Br0.62(4)Cl0.38(4))2Cl2 and NbI2Cl2
  9. Rare earth-rich cadmium compounds RE10TCd3 (RE=Y, Tb, Dy, Ho, Er, Tm, Lu; T=Rh, Pd, Ir, Pt) with an ordered Co2Al5-type structure
  10. Aminkomplexe des Goldes, Teil 9: Gold(I)-halogenid-Komplexe mit primären und azyklischen sekundären Aminen und ihre Oxidation zu Gold(III)-Derivaten
  11. Erratum
  12. Berichtigung: Phosphanchalkogenide und ihre Metallkomplexe. II. Komplexe einiger Gold(I)-Halogenide mit Diphosphanmonochalkogeniden
https://doi.org/10.1515/znb-2017-0136
Keywords for this article
7-chloro-8-nitroquinolone; antibacterial activity; dithizone; Smiles rearrangement; X-ray structure determination

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. Obituary
  4. Gérard Demazeau, 07.06.1943–03.11.2017
  5. Synthesis and reactivity of β-stannylated phenylalanines
  6. Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile promoted by amino-functionalized CoFe2O4@SiO2 nanoparticles under conventional heating, microwave and ultrasound irradiations
  7. Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester
  8. No solid solution compounds in between the binaries: syntheses and crystal structures of Nb(Br0.62(4)Cl0.38(4))2Cl2 and NbI2Cl2
  9. Rare earth-rich cadmium compounds RE10TCd3 (RE=Y, Tb, Dy, Ho, Er, Tm, Lu; T=Rh, Pd, Ir, Pt) with an ordered Co2Al5-type structure
  10. Aminkomplexe des Goldes, Teil 9: Gold(I)-halogenid-Komplexe mit primären und azyklischen sekundären Aminen und ihre Oxidation zu Gold(III)-Derivaten
  11. Erratum
  12. Berichtigung: Phosphanchalkogenide und ihre Metallkomplexe. II. Komplexe einiger Gold(I)-Halogenide mit Diphosphanmonochalkogeniden
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