Synthesis of novel 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones

被引：10
|
作者：
Dzhavakhishvili, S. G. [1 ]
Gorobets, N. Yu. [1 ]
Chernenko, V. N. [1 ]
Musatov, V. I. [1 ]
Desenko, S. M. [1 ]
机构：
[1] Natl Acad Sci Ukraine, Inst Single Crystals, Sci & Technol Corp, UA-61001 Kharkov, Ukraine
来源：
RUSSIAN CHEMICAL BULLETIN | 2008年 / 57卷 / 02期
关键词：
3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H, 6H)-diones; cyclization; 2-[2-cyano-2-(1,3-thiazol-2-yl)ethenyl]-3-oxocyclohex-1-enolates; aromatic amines; micro-wave irradiation; nuclear Overhauser effect;
D O I：
10.1007/s11172-008-0066-z
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient method for the synthesis of novel 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones from various 2-dimethylaminomethylidenecyclohexane-1,3-diones, (1,3-thiazol-2-yl)acetonitriles, and dimethylformamide dimethyl acetal was developed. These transformations proceeded through intermediate 2-[2-(4-aryl-1,3-thiazol-2-yl)-2-cyanoethenyl]-3-oxocyclohex-1-en-1-olates. They were isolated as piperidinium salts and used in further heterocyclization reactions with aromatic amines, giving novel 1-aryl-3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones. These compounds were also obtained by preparative three-step "one pot" synthesis under controlled microwave irradiation.
引用
收藏
页码：422 / 427
页数：6
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