Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

被引:82
|
作者
Schilling, Waldemar [1 ]
Zhang, Yu [1 ]
Riemer, Daniel [1 ]
Das, Shoubhik [1 ]
机构
[1] Georg August Univ Gottingen, Inst Biomol & Organ Chem, Tammannstr, D-37077 Gottingen, Germany
关键词
heterocycles; homogeneous catalysis; oxygenation; pharmaceuticals; photocatalysis; METAL-FREE CATALYST; IN-VITRO; EFFICIENT SYNTHESIS; CYCLIC IMIDES; DERIVATIVES; OXIDATION; ACYLATION; CHEMISTRY; ALCOHOLS; ISATIN;
D O I
10.1002/chem.201904168
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.
引用
收藏
页码:390 / 395
页数:6
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