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

被引：12
作者：
Bonacorso, Helio G. [1 ]
Andrighetto, Rosalia [1 ]
Krueger, Nicolas [1 ]
Zanatta, Nilo [1 ]
Martins, Marcos A. P. [1 ]
机构：
[1] Univ Fed Santa Maria, Nucleo Quim Heterociclos NUQUIMHE, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
来源：
MOLECULES | 2011年 / 16卷 / 04期
关键词：
trifluoromethylated heterocyles; quinolines; naphthyridines; cycloalka[b][1,8]-naphthyridines; aminonaphthyridines; POTENTIAL ANTIHYPERTENSIVE AGENTS; 1,8-NAPHTHYRIDINE DERIVATIVES; REGIOSPECIFIC SYNTHESIS; ENOL ETHERS; CYCLIZATION; KETONES; DESIGN;
D O I：
10.3390/molecules16042817
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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(R-1) OR, where R-1 = 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 cyclocondensation reactions of five-, six-and seven-membered 2-trifluoroacetyl-1-methoxy-cycloalkenes with 2,6-DAP.
引用
收藏
页码：2817 / 2832
页数：16
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