The unexpected cyclization routes of N,N′-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines in polyphosphoric acid medium

作者: Helio G. Bonacorso , Rosália Andrighetto , Nilo Zanatta , Marcos A.P. Martins

DOI: 10.1016/J.TETLET.2010.05.041

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摘要: Abstract The unexpected results of the cyclization reactions N,N′-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C6H4-(NHCR CHC(O)CF3)2], where R = H, Me, and Ph, in a strongly acidic medium (PPA), allowing synthesis new trifluoromethylated heterocycles containing 1,7-phenanthroline nucleus 32–40% yields 7-aminoquinolines (38–40% yields), is reported. bis-enaminoketone intermediates were easily isolated from 4-alkoxy-4-alkyl(aryl)-1,1,1-trifluoroalk-3-en-2-ones with 1,3-phenylenediamine ethanol under mild conditions (68–86% yields).

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