Abstract
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.
Highlights
Phenanthrolines are diazaphenanthrene analogs, polycyclic aromatic hydrocarbon present in sterols, sex hormones, cardiac glycosides, bile acids and in the group of morphine alkaloids.[1]
The purpose of this paper is to report the complete results of the reactions of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1trifluoroalk-3-en-2-ones (1a-j) with 1,3-phenylenediamine to obtain a wide series of ten examples of trifluoroacetyl substituted 1,3-phenylene-bis-enamines (2a-j) and to investigate the chemical behavior of alkyl, aryl and heteroaryl-substituted enamino intermediates (2) for their application in the simultaneous regioselective synthesis of new 2,8- or 4,8-bis(trifluoromethyl)2,10‐bis-alkyl(aryl)-1,7-phenanthrolines (3) and the respective 4-(trifluoromethyl)-7-aminoquinolines (4) under similar reaction conditions as described previously.[29]
A new series of ten bis-enaminone intermediates 2a-j was isolated in satisfactory yields of 47-91%, by the reaction of enones 1a-j with 1,3-phenylenediamine at a molar ratio of 2:1, respectively (Scheme 1)
Summary
Phenanthrolines are diazaphenanthrene analogs, polycyclic aromatic hydrocarbon present in sterols, sex hormones, cardiac glycosides, bile acids and in the group of morphine alkaloids.[1] Heterocycles containing nitrogen atoms such 1,10-phenanthroline,[2] pyronaridine[3] and chloroquine-pyrazole analogs[4] are well known for their antimalarial activity. An example of particular interest of a non-natural antimalarial agent possessing a trifluoromethyl substituted phenanthrene skeleton is halofantrine (Figure 1), an effective drug for the treatment of malaria which possesses good therapeutic effects but some important adverse effects.[5] some angular and linear N-tricyclic similar systems have been documented to possess antiviral activity.[6 ] CF3 Cl N(n-Bu)[2 ] OH. The first phenanthroline, 1,7-phenanthroline was prepared by Skraup and Vortmann[9] in 1882 and the method continues to be one of the best
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