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

被引：0
作者：
S. G. Dzhavakhishvili
N. Yu. Gorobets
V. N. Chernenko
V. I. Musatov
S. M. Desenko
机构：
[1] National Academy of Sciences of Ukraine,Scientific and Technological Corporation “Institute for Single Crystals”
来源：
Russian Chemical Bulletin | 2008年 / 57卷
关键词：
3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1; ,6; )-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：
暂无
中图分类号：
学科分类号：
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
相关论文
共 52 条
[1]  
Crowforth J.(2004)undefined Bioorg. Med. Chem. Lett. 14 1679-undefined
[2]  
Atack J. R.(1999)undefined Tetrahedron Lett. 40 4073-undefined
[3]  
Cook S. M.(2002)undefined J. Org. Chem. 67 9354-undefined
[4]  
Gibson K. R.(2002)undefined J. Med. Chem. 45 1887-undefined
[5]  
Nadin A.(2004)undefined Tetrahedron 60 8633-undefined
[6]  
Owens A. P.(1985)undefined J. Heterocycl. Chem. 22 1503-undefined
[7]  
Pike A.(2005)undefined Zh. Org. Khim. 41 742-undefined
[8]  
Rowley M.(1974)undefined J. Prakt. Chem. 316 684-undefined
[9]  
Smith A. J.(undefined)undefined undefined undefined undefined-undefined
[10]  
Sohal B.(undefined)undefined undefined undefined undefined-undefined
123456