Simultaneous Regioselective Synthesis of Trifluoromethyl-Containing 1,7-Phenanthrolines and Quinolines from Cyclocondensation Reaction of N,N’-Bis(oxotrifluoroalkenyl)-1,3-Phenylenediamines

Este trabalho relata interessantes resultados relativos a síntese convencional de uma nova série de 2,10-dialquil(aril)-4,8-bis (trifluorometil)-1,7-fenantrolinas, em rendimentos de 22-40%, a partir das reações de ciclização de N,N’-bis(oxotrifluoralquenil)-1,3-fenilenodiaminas [1,3-C6H4-(NHCR=CHC(O)CF3)2] em um meio fortemente ácido (PPA) e na ausência de solvente. A rota sintética também permitiu o isolamento simultâneo de uma nova série de 2-alquil(aril/heteroaril)-4-trifluormetil-7-aminoquinolinas, em 20-73 % de rendimento. As enaminonas precursoras foram obtidas a partir da reação de 4-alcóxi-1,1,1-triflúor-3-alquen-2-onas [CF3C(O)CH=C(R)OR1, onde R = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furil e R1 = Me, Et] com 1,3-fenilenodiamina em condições brandas, em rendimentos 47-91%. 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 22-40 % yields, from cyclization reactions of N,N’-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C6H4-(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 20-73 % yields, simultaneously. The enaminone precursors were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(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 47-91 % yields