6,8-Dibromo-4-chloroquinoline-3-carbaldehyde as a synthon in the development of novel 1,6,8-triaryl-1H-pyrazolo[4,3-c]quinolines

Add time:07/16/2019    Source:sciencedirect.com

2-Amino-3,5-dibromoacetophenone undergoes Vilsmeier reaction with a phosphoryl chloride–dimethylformamide mixture to afford 6,8-dibromo-4-chloroquinoline-3-carbaldehyde. The latter was reacted with arylhydrazine hydrochlorides in ethanol in the presence of triethylamine to afford the corresponding arylhydrazone derivatives. These hydrazones were, in turn, cyclized with ethanolic KOH (5% in ethanol) to afford the corresponding 1-aryl-6,8-dibromo-1H-pyrazolo[4,3-c]quinolines. Suzuki–Miyaura cross-coupling of these 1-aryl-6,8-dibromo-1H-pyrazolo[4,3-c]quinolines with arylboronic acids afforded novel 1,6,8-triaryl-1H-pyrolo[4,3-c]quinolines.

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