ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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, and Sarai Vega-Rodríguez

Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, San Luis Potosí, Mexico

E-mail: sleyva@uaslp.mx

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

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-016-0016-4

Chemical Papers 71 (5) 939–947 (2017)