Transforming inexpensive quinolines into complex drug candidates

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Pharmaceuticals,Diseases And Conditions,Chemistry

An innovative synthesis strategy opened up the way to 2D/3D fused frameworks using inexpensive quinolines as feedstock, report scientists. By leveraging a light-sensitive borate intermediate, the scientists could transform quinoline derivatives into a great variety of 2D/3D fused frameworks in a straightforward and cost-effective manner.

Their findings are expected to enable the synthesis of highly customizable drug candidates.

One of the most attractive ways to use quinolines as feedstock for 2D/3D frameworks is through dearomative photocycloadditions. This process involves destabilizing one of the aromatic rings in quinoline, using light and sometimes a catalyst, so that a reactant can 'latch' onto the ring, forming the target compound. Despite many efforts, most studies have reported photocycloadditions happening on quinoline's benzene ring side, while few have targeted the pyridine side.

Seeking to shed light on the mechanisms underlying their newfound strategy, the team conducted a series of experiments and theoretical analyses. They determined that quinoline reacts with an organolithium compound first and then with H-B to form an intermediate borate complex.

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