Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines form cyclocondensation reaction of N,N′-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

Article abstract of DOI:10.1590/S0103-50532011000800005

This paper reports interesting results of the conventional synthesis of a new series of 2,10-dialkyl(aryl)-4,8-bis(trifluoromethyl)-1,7-phenanthrolines, in 22-40percent yields, form cyclization reactions of N,N′- bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C₆H ₄-(NHCR=CHC(O)CF₃)₂] in a strongly acidic medium (PPA) and absence of solvent. The synthetic route also allowed the isolation of a new series of 2-alkyl(aryl/heteroaryl)-4-trifluoromethyl-7- aminoquinolines, in 20-73percent yields, simultaneously. The enaminone precursors were obtained form the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF ₃C(O)CH=C(R)OR¹, where R = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO₂Ph, 2-furyl and R¹ = Me, Et] with 1,3-phenylenediamine under mild conditions, in 47-91percent yields.