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首页> 外文期刊>Journal of the Brazilian Chemical Society >Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines
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Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

机译:N,N'-双(氧代三氟烯基)-1,3-苯二胺的环缩合反应同时选择性合成含三氟甲基的1,7-菲咯啉和喹啉

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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.
机译:本文报道了由N的环化反应以22-40%的产率常规合成一系列新的2,10-二烷基(芳基)-4,8-​​双(三氟甲基)-1,7-菲咯啉的有趣结果。 ,N'-双(氧三氟烯基)-1,3-苯二胺[1,3-C6H4-(NHCR = CHC(O)CF3)2]在强酸性介质(PPA)中且没有溶剂。合成路线还允许以20-73%的收率同时分离出一系列新的2-烷基(芳基/杂芳基)-4-三氟甲基-7-氨基喹啉。烯胺酮前体是由4-烷氧基-1,1,1-三氟烷-3-en-2-ones [CF3C(O)CH = C(R)OR1,其中R = H,Me,Ph, [4-MePh,4-OMePh,4-ClPh,4-FPh,4-BrPh,4-NO2Ph,2-呋喃基和R1 = Me,Et]与1,3-苯二胺在温和条件下的收率为47-91% 。

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