Chemical Papers

, Volume 71, Issue 5, pp 939–947 | Cite as

An efficient reduction of azide to amine: a new methodology to synthesize ethyl 7-amino-1-ethyl-6,8-difluoroquinolone-3-carboxylate and its spectroscopic characterization

  • Socorro Leyva-Ramos
  • Hiram Hernández-López
  • Rogelio Jiménez-Cataño
  • Luis Chacón-García
  • Sarai Vega-Rodríguez
Original Paper
First Online:
Received:
Accepted:

Abstract

Most of the quinolone antibacterial research has been focused on the functionality at C-7 position where the nature of substituents is responsible for antibacterial spectrum, potency, bioavailability, and side effects of the quinolones. Then, a 7-amino-fluoroquinolone could be the starting point of a wide variety of potentially useful compounds like tetracyclic and tricyclic quinolones or secondary amines with side chain derivatives. This attracted our attention to synthesize a 7-azide-fluoroquinolone, which could be converted to amine performing a photochemical reaction using CuI as catalyst. FT-IR and H1 NMR spectra of the final product, ethyl 7-amino-1-ethyl-6,8-difluoroquinolone-3-carboxylate, suggests the formation of dimers, a feature already observed in norfloxacin.

Keywords

Anti-infective compound Aminofluoroquinolone dimer π–π interaction 7-amino-fluoroquinolone 7-azide-fluoroquinolone 
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Notes

Acknowledgements

We wish to thank CONACYT (SEP-82585) and UASLP (C11-FRC-09-37.7) for their financial support.

Supplementary material

11696_2016_16_MOESM1_ESM.docx (10.1 mb)
Supplementary material 1 (DOCX 10298 kb)

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2016

Authors and Affiliations

  • Socorro Leyva-Ramos
    • 1
  • Hiram Hernández-López
    • 2
  • Rogelio Jiménez-Cataño
    • 1
  • Luis Chacón-García
    • 3
  • Sarai Vega-Rodríguez
    • 1
  1. 1.Facultad de Ciencias QuímicasUniversidad Autónoma de San Luis PotosíSan Luis PotosíMexico
  2. 2.Unidad Académica de Ciencias Químicas, Universidad Autónoma de ZacatecasZacatecasMexico
  3. 3.Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de HidalgoMoreliaMexico

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