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Quinolines and indoles are both very common core motifs in drug molecules. Because they differ by just a single carbon in their ring frameworks, it would be useful to interconvert them during structure-activity relationship studies. However, aromatic stabilization in these compounds makes that process difficult. Woo et al. now report that narrow-wavelength irradiation of quinoline N-oxides in the near-ultraviolet range followed by acid treatment cleanly excises a ring carbon to produce an indole, avoiding secondary photoproducts that were previously observed using broadband light.
Quinolines and indoles are both very common core motifs in drug molecules. Because they differ by just a single carbon in their ring frameworks, it would be useful to interconvert them during structure-activity relationship studies. However, aromatic stabilization in these compounds makes that process difficult. Woo et al. now report that narrow-wavelength irradiation of quinoline N-oxides in the near-ultraviolet range followed by acid treatment cleanly excises a ring carbon to produce an indole, avoiding secondary photoproducts that were previously observed using broadband light.
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Quinolines and indoles are both very common core motifs in drug molecules. Because they differ by just a single carbon in their ring frameworks, it would be useful to interconvert them during structure-activity relationship studies. However, aromatic stabilization in these compounds makes that process difficult.