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

被引：17

作者：

Maluleka, Marole M. ^{[1
]}

Mphahlele, Malose J. ^{[1
]}

机构：

[1] Univ S Africa, Coll Sci Engn & Technol, Dept Chem, ZA-0003 Pretoria, South Africa

来源：

TETRAHEDRON | 2013年 / 69卷 / 02期

关键词：

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; BENZODIAZEPINE-RECEPTOR LIGANDS; ONE-POT SYNTHESIS; VILSMEIER; DERIVATIVES; QUINOLINES; CYCLIZATION; COMPLEXES; COUPLINGS; EMISSION;

D O I：

10.1016/j.tet.2012.10.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：699 / 704

页数：6

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