Ruiz S, Carrera C, Villuendas P, Urriolabeitia E P
Instituto de Síntesis Química y Catálisis Homogénea, CSIC-Universidad de Zaragoza, Pedro Cerbuna 12, E-50009 Zaragoza, Spain.
Org Biomol Chem. 2017 Oct 31;15(42):8904-8913. doi: 10.1039/c7ob01497j.
The synthesis of fused heterocycle-pyridinones has been achieved by oxidative coupling of N-unprotected primary heterocycle-amides with internal alkynes. The reaction, which is catalysed by Ru(ii) and assisted by Cu(ii), takes place through C-H and N-H bond activation of the heterocyclic unit. The scope of the reaction includes a variety of alkynes, electron-rich thiophenes, furans and pyrroles, and even electron-poor pyridines. The reaction is fully regioselective with respect to the position of the C-H bond activation due to the directing effect of the amide group. In the same way, the synthesis of fused heterocycle-pyrones (isocoumarins) has been developed by Ru-catalysed oxidative coupling of heterocyclic carboxylic acids and internal alkynes. The reaction involves C-H and O-H bond activation. This reaction also has a broad scope, from electron-rich thiophenes, furans and pyrroles to electron-deficient pyridines and quinolines.
通过N-未保护的伯杂环酰胺与内炔烃的氧化偶联实现了稠合杂环吡啶酮的合成。该反应由Ru(ii)催化并由Cu(ii)辅助，通过杂环单元的C-H和N-H键活化进行。反应范围包括各种炔烃、富电子的噻吩、呋喃和吡咯，甚至贫电子的吡啶。由于酰胺基团的导向作用，该反应在C-H键活化位置上具有完全的区域选择性。同样，通过Ru催化的杂环羧酸与内炔烃的氧化偶联开发了稠合杂环吡喃酮（异香豆素）的合成。该反应涉及C-H和O-H键活化。该反应也具有广泛的范围，从富电子的噻吩、呋喃和吡咯到缺电子的吡啶和喹啉。
