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A Radical-Chemistry Approach to 2-Arylquinolines

Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N-Iodosuccinimide: H. Naruto, H. Togo
Synthesis 2020, 52, DOI: 10.1055/s-0039-1691642

 

The quinoline scaffold is present in many bioactive and natural molecules, such as the antimalarials quinine and chloroquine, which explains the enormous interest and the large number of synthetic methods developed for accessing this heterocyclic ring, such as the classical Friedländer or the Skraup synthesis. In line with the recent upsurge of interest in radical chemistry, the group of Professor Hideo Togo from Chiba University (Japan) has recently described a novel strategy to prepare 2-arylquinolines from the corresponding nitriles.

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Professor Togo said: “The quinoline core could be prepared by the reaction of 2-arylethylmagnesium bromides, nitriles, and N-iodosuccinimide via imino-nitrogen-centered radicals formed from N-iodo 2-arylethylketimines under irradiation with a tungsten lamp.”

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