Journal
TETRAHEDRON
Volume 69, Issue 2, Pages 699-704Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.10.103
Keywords
6,8-Dibromo-4-chloroquinoline-3-carbaldehyde; N '-[(6,8-Dibromo-4-chloroquinolin-3-yl) methylene]-2-arylhydrazides; 1-Aryl-6,8-dibromo-1H-pyrazolo[4,3-c]quinolines; Suzuki-Miyaura cross-coupling; 1,6,8-Triaryl-1H-pyrazolo[4,3-c]quinolines
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Funding
- University of South Africa
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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. (c) 2012 Elsevier Ltd. All rights reserved.
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