1233947-72-2Relevant academic research and scientific papers
Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines form cyclocondensation reaction of N,N′-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines
Bonacorso, Helio G.,Andrighetto, Rosa?lia,Kru?ger, Ni?colas,Martins, Marcos A.P.,Zanatta, Nilo
experimental part, p. 1426 - 1438 (2011/10/13)
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.
The unexpected cyclization routes of N,N′-bis(oxotrifluoroalkenyl)-1, 3-phenylenediamines in polyphosphoric acid medium
Bonacorso, Helio G.,Andrighetto, Rosália,Zanatta, Nilo,Martins, Marcos A. P.
experimental part, p. 3752 - 3755 (2010/08/20)
The unexpected results of the cyclization reactions of N,N′- bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C6H 4-(NHCR=CHC(O)CF3)2], where R = H, Me, and Ph, in a strongly acidic medium (PPA), allowing the synthesis of new trifluoromethylated heterocycles containing the 1,7-phenanthroline nucleus in 32-40% yields and 7-aminoquinolines (38-40% yields), is reported. The bis-enaminoketone intermediates were easily isolated from the reactions of 4-alkoxy-4-alkyl(aryl)-1,1,1-trifluoroalk-3-en-2-ones with 1,3-phenylenediamine in ethanol under mild conditions (68-86% yields).
