1. Synthesis of novel 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1 H ,6 H )-diones.
- Author
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S. Dzhavakhishvili, N. Gorobets, V. Chernenko, V. Musatov, and S. Desenko
- Subjects
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ORGANIC synthesis , *THIAZOLES , *QUINOLINE , *INTERMEDIATES (Chemistry) , *PIPERIDINE , *RING formation (Chemistry) , *AROMATIC amines - Abstract
Abstract 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. [ABSTRACT FROM AUTHOR]
- Published
- 2008
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