Synthesis of novel 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones |
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Authors: | S. G. Dzhavakhishvili N. Yu. Gorobets V. N. Chernenko V. I. Musatov S. M. Desenko |
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Affiliation: | (1) Scientific and Technological Corporation “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 61001 Kharkov, Ukraine |
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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. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 412–417, February, 2008. |
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Keywords: | 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 |
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