Síntese de 1,7-fenantrolinas e 7-aminoquinolinas trifluormetil substituídas

Abstract

This work, at first, describes the synthesis and characterization of new series of (Z,Z)-N,N -bis(oxotrifluoroalkenyl)-1,3-phenylenediamines by the addition/elimination reaction of β-alkoxyvinyl trifluoromethyl ketones with 1,3-phenylenediamine, in 47-91 % yields. The 4-alkyl[aryl(heteroaryl)]-4-alkoxy-1,1,1-trifluoro-3-alken-2-ones, of general formula F3C-C(O)-CH=C(R1)-OR where R = Me, Et and R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furoyl, 2-thienyl, were obtained from trifluoroacetylation reactions of enolethers or acetals derived of acyclic ketones. Subsequently is reported the synthesis and characterization of new series of bis-trifluoromethyl substituted 1,7-phenanthrolines, from cyclization reactions of bis-enaminones in a strongly acidic medium (PPA) and absence of solvent, in 22-40 % yields, where for the first time two interesting manners of cyclization were observed, in the synthesis of two different angular structures. The products were identified as 2,8-bis(trifluoromethyl)-1,7-phenanthroline and 2,10-dialkyl(aryl)-4,8-(bis-trifluoromethyl)-1,7-phenanthrolines. The synthetic route used herein also allowed the isolation of new series of 7-aminoquinolines structures in 20-45 % yields. Compounds were characterized by 1H, 13C NMR spectroscopy, by Mass Spectrometry, their structures also were established by X-ray diffraction and their purity was confirmed by elemental analysis.