Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China 116023.
J Org Chem. 2010 Nov 5;75(21):7487-90. doi: 10.1021/jo101596d.
A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C-H activation of benzamides has been developed. Ag(2)CO(3) proved to be an optimal oxidant when MeCN was used as a solvent, and RhCp*Cl(2) was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C-H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles.
一种从苯甲酰胺和炔烃高效且简便地合成异喹啉的方法已经发展起来。在使用 MeCN 作为溶剂时，Ag(2)CO(3)被证明是一种最佳的氧化剂，RhCp*Cl(2)则被用作一种高效的催化剂。N-烷基和 N-芳基的仲苯甲酰胺都可以作为有效的底物。此外，伯苯甲酰胺与两个炔烃单元反应，通过双 C-H 活化和氧化偶联生成三环产物。结构相关的 1-羟基异喹啉的反应性也得到了证明，其中可以生成含 N 和含 O 的铑环中间体，从而构建不同的含 O 或含 N 的杂环。
