2 research outputs found
Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents
We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some of the synthesized 4-carbinol quinolines have shown interesting antiproliferative properties, their hydroxyl group being a suitable amino group bioisostere. We also report a two-step approach for optically active derivatives
Base-Controlled Regioselective Functionalization of Chloro-Substituted Quinolines
We prepared a number of di- and trifunctionalized
quinolines by
selective metalation of chloro-substituted quinolines with metal amides
followed by reaction with different electrophiles. Metalation of the
C-3 position of the quinolinic ring with lithium diisopropylamide
at −70 °C is easy to achieve, whereas reaction with lithium–magnesium
and lithium–zinc amides affords C-2 or C-8 functionalized derivatives
in a regioselective fashion. These complementary methods could be
rationalized by DFT calculations and are convenient strategies toward
the synthesis of bioactive quinoline derivatives such as chloroquine
analogues