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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

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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 trifluoromethylated heterocyles; quinolines; naphthyridines; cycloalka[b][1,8]-naphthyridines; aminonaphthyridines
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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