Pemberton Nils, Aberg Veronica, Almstedt Hanna, Westermark Andreas, Almqvist Fredrik
Organic Chemistry, Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden.
J Org Chem. 2004 Nov 12;69(23):7830-5. doi: 10.1021/jo048554y.
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 traditional 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.
通过采用微波辅助有机合成（MAOS）的有效条件，已成功在高度取代的双环2-吡啶酮中引入氨甲基取代基。通过氰基卤化反应引入伯氨基甲基取代基，随后用硼烷二甲硫醚还原所得腈。在这两种转化反应中，微波辐射均优于传统条件，且伯胺的总收率良好（三步反应收率为55 - 58%）。为了在2-吡啶酮骨架中引入叔氨基甲基取代基，使用预制亚胺盐的微波辅助曼尼希反应被证明是有效的。因此，以48 - 93%的收率得到了高度取代的2-吡啶酮。
