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A series of KF/Al2O3 catalyzed Michael-addition reactions between malononitrile and a,b-unsaturated cycloke-tones 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-1-one and malononitrile. However, if the temperature was increased to 80 ℃, 2-amino-3-cyano-4- aryl-4H-benzo[h]chromene derivatives were obtained in high yields. When the a,b-unsaturated ketones were re-placed by 2,6-biarylmethylidenecyclohexanone or 2,5-biarylmethylidenecyclopentanone, another series of 2-amino- 3-cyano-4H-pyran derivatives was isolated successfully. The structures of the products were confirmed by X-ray diffraction analysis.
A series of KF / Al2O3 catalyzed Michael-addition reactions between malononitrile and a, b-unsaturated cycloke-tones in DMF solution were studied. At room temperature, 2-cyano- -tetrahydronaphthalen-1-one-2-yl) propionitrile derivatives were synthesized by the reaction between 2-arylmethylidene-1,2,3,4-tetra- hydronaphthalen-1-one and malononitrile. However, When the a, b-unsaturated ketones were re-placed by 2,6-biarylmethylidenecyclohexanone or 2,5 -biarylmethylidenecyclopentanone, another series of 2-amino- 3-cyano-4H-pyran derivatives was isolated successfully. The structures of the products were confirmed by X-ray diffraction analysis.