Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500037, India.
Org Biomol Chem. 2020 Mar 25;18(12):2307-2311. doi: 10.1039/d0ob00250j.
A β-carboline directed regioselective C-H activation protocol for hydroxylation has been developed by employing Cu(OAc)2, a cost-effective 3d metal. This fastidious reaction proceeds under microwave irradiation and furnishes exclusively ortho-hydroxylated products with moderate to good yields under greener reaction conditions. Gratifyingly, this approach retains considerable functional group tolerance and is feasible on both electron-rich and electron-deficient substrates. This protocol signifies monohydroxylation on β-carboline via C-H functionalization which leads into development of biologically relevant molecules. The reaction mechanism was confirmed by intercepting and characterizing all the proposed intermediates by ESI-QTOF-MS.
一种β-咔啉导向的区域选择性 C-H 活化羟化方法已经通过使用成本效益高的 3d 金属 Cu(OAc)2 得到开发。这种苛刻的反应在微波辐射下进行，在更环保的反应条件下，以中等至良好的收率提供了唯一的邻位羟化产物。令人高兴的是，这种方法保留了相当大的官能团耐受性，并且在富电子和缺电子底物上都是可行的。该方案通过 C-H 功能化实现了β-咔啉的单羟化，从而开发出具有生物相关性的分子。通过 ESI-QTOF-MS 拦截和表征所有提议的中间体，证实了反应机理。
