Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

Journal of the Brazilian Chemical Society

Krüger, Nícolas¹  Zanatta, Nilo¹  Andrighetto, Rosália¹  Bonacorso, Helio G.¹  Martins, Marcos A. P.¹  Universidade Federal de Santa Maria, Santa Maria, Brazil¹ 

关键词: enones;    enaminoketones;    phenanthrolines;    quinolines;    PPA;   

DOI  :  10.1590/S0103-50532011000800005

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

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.

【 授权许可】

Unknown