General pathway for a convenient one-pot synthesis of trifluoromethyl-containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and fused cycloalkane analogues
| Autor: | Nícolas Krüger, Rosália Andrighetto, Marcos A. P. Martins, Nilo Zanatta, Helio G. Bonacorso |
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| Rok vydání: | 2011 |
| Předmět: |
quinolines
General method Magnetic Resonance Spectroscopy One-pot synthesis Pharmaceutical Science trifluoromethylated heterocyles naphthyridines cycloalka[b][1 8]-naphthyridines aminonaphthyridines Gas Chromatography-Mass Spectrometry Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Drug Discovery Organic chemistry Physical and Theoretical Chemistry Alkyl chemistry.chemical_classification Trifluoromethyl Aryl Organic Chemistry Cycloparaffins Cycloalkane chemistry Chemistry (miscellaneous) Molecular Medicine |
| Zdroj: | Molecules Molecules, Vol 16, Iss 4, Pp 2817-2832 (2011) Molecules; Volume 16; Issue 4; Pages: 2817-2832 |
| ISSN: | 1420-3049 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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