Synthesis of 1-Alkylisoquinolines via Radical Cyclization

Metal-Free Radical Cyclization of Vinyl Isocyanides with Alkanes: Synthesis of 1-Alkylisoquinolines: D. Xue, Y. Xue, H. Yu, L. Shao
Synthesis 2018, DOI: 10.1055/s-0037-1610661

Traditional synthetic approaches to the biologically important isoquinoline core – such as Bischler–Napieralski, Pomeranz–Fritsch and Pictet–Spengler reactions – often rely on the use of harsh reaction conditions, which are not always compatible with densely functionalized molecules. Recently, the group of Professor Liming Shao from Fudan University (Shanghai, P. R. of China) described the use of isocyanides, which are versatile building blocks that can be employed as building blocks for constructing heterocycles, for accessing 1-alkylisoquinolines.

Professor Liming Shao said: “We developed a metal-free tandem oxidative cyclization reaction of vinyl isocyanides with alkanes to synthesize 1-alkylisoquinolines. The method offers a unique, simple and efficient strategy for the convenient preparation of pharmacologically interesting isoquinolines with excellent functional group tolerance and broad substrate scope.”
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