Tetrahedron

Mechanism and synthesis of pharmacologically active quinolones from Morita–Baylis–Hillman adducts

GW Amarante, M Benassi, RN Pascoal, MN Eberlin…

Index: Amarante, Giovanni W.; Benassi, Mario; Pascoal, Robert N.; Eberlin, Marcos N.; Coelho, Fernando Tetrahedron, 2010 , vol. 66, # 24 p. 4370 - 4376

Full Text: HTML

Citation Number: 31

Abstract

The synthesis of quinolones from Morita–Baylis–Hillman (MBH) adducts is reported. The quinolone skeleton is formed via a TFA-mediated cyclization of the MBH adduct, and a mechanism study using ESI (+)-MS (/MS) has indicated the role played by TFA in this key reaction step. The total syntheses of Norfloxacin and a benzyl quinolone carboxylic acid (BQCA) derivative are described. Norfloxacin is a fluoroquinolonic antibacterial drug ...