Molecules 2011, 16(4), 2817-2832; doi:10.3390/molecules16042817
Article

General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues

Helio G. Bonacorso* email, Rosália Andrighetto, Nícolas Krüger, Nilo Zanatta and Marcos A. P. Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil
* Author to whom correspondence should be addressed.
Received: 15 February 2011; in revised form: 24 March 2011 / Accepted: 28 March 2011 / Published: 30 March 2011
(This article belongs to the Special Issue Fluorine Chemistry)
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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.
Keywords: trifluoromethylated heterocyles; quinolines; naphthyridines; cycloalka[b][1,8]-naphthyridines; aminonaphthyridines

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MDPI and ACS Style

Bonacorso, H.G.; Andrighetto, R.; Krüger, N.; Zanatta, N.; Martins, M.A.P. General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues. Molecules 2011, 16, 2817-2832.

AMA Style

Bonacorso HG, Andrighetto R, Krüger N, Zanatta N, Martins MAP. General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues. Molecules. 2011; 16(4):2817-2832.

Chicago/Turabian Style

Bonacorso, Helio G.; Andrighetto, Rosália; Krüger, Nícolas; Zanatta, Nilo; Martins, Marcos A. P. 2011. "General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues." Molecules 16, no. 4: 2817-2832.

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