Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1$H)$-ones in a palladium catalyzed Sonogashira cross-coupling reaction

Authors : Malose Jack MPHAHLELE, Felix Adetunji OYEYIOLA

Pages : 1216-1231

View : 15 | Download : 8

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Pd/C-PPh$_{3}$--CuI catalyzed Sonogashira cross-coupling of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4insert ignore into journalissuearticles values(1$H);$-ones with phenyl acetylene or 3-butyn-1-ol afforded the corresponding 8-alkynylated quinolin-4insert ignore into journalissuearticles values(1$H);$-one derivatives, exclusively. Double carbo-substitution to afford the 6,8-dialkynyl derivatives was observed when PdCl$_{2}$insert ignore into journalissuearticles values(PPh$_{3});_{2}$ was used as Pdinsert ignore into journalissuearticles values(0); source. The monoalkynylated derivatives were, in turn, subjected to PdCl$_{2}$ in acetonitrile under reflux to afford either the corresponding 2,4-diaryl-8-bromopyrrolo[3,2,1-\textit{ij}]quinolinones or the 8-insert ignore into journalissuearticles values(4-hydroxybutanoyl);-substituted quinolinone derivatives, exclusively. Suzuki--Miyaura cross-coupling of the 2-aryl-6-bromo-8-insert ignore into journalissuearticles values(alkynyl);quinolin-4-ones afforded the 2,4,8-trisubstituted pyrrolo[3,2,1-\textit{ij}]quinolin-6-ones.
Keywords : 2 Aryl 6, 8 dibromo 2, 3 dihydroquinolin 4 1 H, ones, cross coupling, pyrrolo 3, 2, 1 extit ij quinolin 6 ones