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Base-Controlled Regioselective Functionalization of Chloro-Substituted Quinolines

2017; American Chemical Society; Volume: 83; Issue: 2 Linguagem: Inglês

10.1021/acs.joc.7b02855

1520-6904

Valter E. Murie, Rodolfo Hideki Vicente Nishimura, Larissa Araújo Rolim, Ricardo Vessecchi, Norberto Peporine Lopes, Giuliano C. Clososki,

Catalytic C–H Functionalization Methods

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.