An alternative approach toward 2-aryl-2H-pyrazolo[4,3-c]-quinolin-3-ones by a multistep synthesis

被引：16

作者：

Lopez Rivilli, Marisa J. ^{[1
]}

Moyano, Elizabeth L. ^{[1
]}

Yranzo, Gloria I. ^{[1
]}

机构：

[1] Univ Nacl Cordoba, INFIQC, Dept Quim Organ, Fac Ciencias Quim, RA-5000 Cordoba, Argentina

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 03期

关键词：

BENZODIAZEPINE-RECEPTOR LIGANDS; GOULD-JACOBS REACTION; BZR; PHARMACOPHORE; DERIVATIVES; BINDING; SITE;

D O I：

10.1016/j.tetlet.2009.10.123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2-aryl-2H-pyrazolo[4,3-c]quinolin-3-ones derivatives 6 and 7 was conveniently prepared. A multistep synthesis was carried out starting from dichloro- and bromoanilines (1a-b) and diethyl 2-(ethoxymethylene)malonate using a slightly modified Gould-Jacobs reaction. In this work we present a novel chlorination strategy to prepare quinoline derivatives 4 in excellent yields as key intermediates in the synthesis of the target compounds. Several reaction conditions were evaluated to optimize the formation of pyrazoloquinolinone nucleus. Differences in chemical behavior of both chloroquinolinones 4a-b with aryl and benzyl-hydrazines are also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：478 / 481

页数：4

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