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KMID : 1059519850290010061
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Journal of the Korean Chemical Society
1985 Volume.29 No. 1 p.61 ~ p.66
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Synthesis of 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones
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Ahn Yong-Hyun
Lee Yun-Yeong
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Abstract
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The preparation of 2-(2,2,2-trichloroethylidene)cyclohexanone(1), as a key compound for synthesizing 2-substituted 5,6,7,8-tetrahydro-3-cinnolinones, was attempted by the enamine condensation of cyclohexanone with chloral. However, the condensation of 1-morpholino-1-cyclohexene (2) with chloral afforded 2-(1-hydroxy-2,2,2-trichloroethyl)cyclohexanone (3), and its dehydration led to 2-(2,2-dichlorovinyl)-2-cyclohexenone (4). 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones could be synthesized using morpholinium α-(4-morpholinyl)-α-(2-oxocyclohexyl)-acetate (5) in place of 1 with arylhydrazines.
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