Microwave-assisted synthesis of highly substituted aminomethylated 2-pyridones

被引:38
作者
Pemberton, N [1 ]
Åberg, V [1 ]
Almstedt, T [1 ]
Westermark, A [1 ]
Almqvist, F [1 ]
机构
[1] Umea Univ, Dept Chem, SE-90187 Umea, Sweden
关键词
D O I
10.1021/jo048554y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By employing microwave-assisted organic synthesis (MAOS) efficient conditions to introduce aminomethylene substituents in highly substituted bicyclic 2-pyridones have been established. Primary amino methylene substituents were introduced via a cyanodehalogenation followed by a borane dimethyl sulfide reduction of the afforded nitrile. In both of these transformations, microwave irradiation proved to be superior to traditiohal conditions and the primary amines were obtained in good overall yields (55-58% over three steps). To incorporate tertiary aminomethylene substituents in the 2-pyridone framework, a microwave-assisted Mannich reaction using preformed iminium salts proved to be effective. Thus highly substituted 2-pyridones were obtained in 48-93% yields.
引用
收藏
页码:7830 / 7835
页数:6
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