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

详细信息    查看全文

• 作者：Marole M. Maluleka ; Malose J. Mphahlele ; ^{mphahmj@unisa.ac.za}
• 关键词：6 ; 8-Dibromo-4-chloroquinoline-3-carbaldehyde ; N&prime ; -[(6 ; 8-Dibromo-4-chloroquinolin-3-yl)methylene]-2-arylhydrazides ; 1-Aryl-6 ; 8-dibromo-1H-pyrazolo[4 ; 3-c]quinolines ; Suzuki&ndash ; Miyaura cross-coupling ; 1 ; 6 ; 8-Triaryl-1H-pyrazolo[4 ; 3-c]quinolines
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：14 January, 2013
• 年：2013
• 卷：69
• 期：2
• 页码：699-704
• 全文大小：316 K

文摘

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.