4-hydroxy-2-quinolones. 204.* synthesis, bromination, and analgetic properties of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid arylalkylamides

被引：14
|
作者：
Ukrainets, I. V. [1 ]
Mospanova, E. V. [2 ]
Jaradat, N. A. [3 ]
Bevz, O. V. [1 ]
Turov, A. V. [4 ]
机构：
[1] Natl Univ Pharm, UA-61002 Kharkov, Ukraine
[2] Vladimir Dal Eastern Ukraine Natl Univ, Inst Chem Technol, UA-93003 Rubizhne, Ukraine
[3] An Najah Natl Univ, Pharmaceut Coll, Nablus, Israel
[4] Taras Shevchenko Kyiv Natl Univ, UA-01033 Kiev, Ukraine
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2012年 / 48卷 / 09期
关键词：
4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides; amidation; analgesic activity; bromination; halocyclization; ALKYLAMIDES;
D O I：
10.1007/s10593-012-1143-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple method has been proposed and used for the preparation of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-di-hydroquinoline-3-carboxylic acid arylalkylamides. Similar to alkylamides of this acid, the arylalkylamides obtained are halogenated with cyclization by one equivalent of molecular bromine to give the corresponding 2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carbox-amides. However, the reaction proceeds quite differently when using an excess of bromine. After the usual initial oxazole ring closure, the excess bromine brominates the aromatic ring of the amide fragment. The results of testing for the analgesic activity of these products are presented.
引用
收藏
页码：1347 / 1356
页数：10
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