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Michael‐Addition Reaction of Malononitrile with α,β‐Unsaturated Cycloketones Catalyzed by KF/Al 2 O 3
Author(s) -
Wang XiangShan,
Shi DaQing,
Tu ShuJiang
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040220203
Subject(s) - malononitrile , chemistry , propionitrile , michael reaction , catalysis , pyran , aryl , medicinal chemistry , organic chemistry , acetonitrile , alkyl
A series of KF/Al 2 O 3 catalyzed Michael‐addition reactions between malononitrile and α,β‐unsaturate cycloketones in DMF solution were studied. At room temperature, 2‐cyano‐3‐aryl‐3–(1, 2, 3, 4‐tetrahydronaphthalen‐1‐one‐2‐yl) propionitrile derivatives were synthesized by the reaction between 2‐arylmethylidene‐1, 2, 3, 4‐tetra‐hydronaphthalen‐l‐one and malononitrile. However, if the temperature was increased to 80 C, 2‐amino‐3‐cyano‐4‐aryl‐4 H ‐benzo[ h ]chromene derivatives were obtained in high yields. When the α,β‐unsaturated ketones were replaced by 2, 6‐biarylmethylidenecyclohexanone or 25‐biarylmethylidenecyclopentanone, another series of 2‐amino‐3‐cyano‐4 H ‐pyran derivatives was isolated successfully. The structures of the products were confirmed by X‐ray diffraction analysis.