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

作者：Leyva Ramos Socorro^*; Hernandez Lopez Hiram; Jimenez Catano Rogelio; Chacon Garcia Luis; Vega Rodriguez Sarai

来源：Chemical Papers, 2017, 71(5): 939-947.

DOI：10.1007/s11696-016-0016-4

• Anti-infective compound
• Aminofluoroquinolone dimer
• pi-pi interaction
• 7-amino-fluoroquinolone
• 7-azide-fluoroquinolone

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 H-1 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.

• 出版日期2017-5