title: General pathway for a convenient one-pot synthesis of trifluoromethyl-containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and fused cycloalkane analogues.
abstract: A convenient and general method for the synthesis in 26-73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF₃C(O)CH=C(R¹)OR, where R¹ = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO₂Ph, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), under mild conditions, is described. Another synthetic route also allowed the synthesis of 2-amino-5-trifluoromethyl-cycloalka[b][1,8]naphthyridines in 33-36% yields, from direct or indirect cyclo-condensation reactions of five-, six- and seven-membered 2-trifluoroacetyl-1-methoxy-cycloalkenes with 2,6-DAP.
authors: Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil. heliogb@base.ufsm.br
authors: Helio G
authors: HG
authors: Bonacorso
authors: Rosália
authors: R
authors: Andrighetto
authors: Nícolas
authors: N
authors: Krüger
authors: Nilo
authors: N
authors: Zanatta
authors: Marcos A P
authors: MA
authors: Martins
mesh_terms: D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003516:Cycloparaffins; D009287:Naphthyridines