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Michael-Addition Reaction of Malononitrile with α,β-Unsaturated Cycloketones Catalyzed by KF/Al2O3
引用本文:王香善 史达清 屠树江. Michael-Addition Reaction of Malononitrile with α,β-Unsaturated Cycloketones Catalyzed by KF/Al2O3[J]. 中国化学, 2004, 22(2): 122-125. DOI: 10.1002/cjoc.20040220203
作者姓名:王香善 史达清 屠树江
作者单位:DepartmentofChemistry,XuzhouNormalUniversity,Xuzhou,Jiangsu221116,China
摘    要:A series of KF/Al2O3 catalyzed Michael-addition reactions between malononitrile and α,β-unsaturated 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-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 α,β-unsaturated ketones were replaced 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.

关 键 词:丙二腈 α  β-不饱和环酮 催化剂 KF/Al2O3 迈克尔加成反应

Michael‐Addition Reaction of Malononitrile with α,β‐Unsaturated Cycloketones Catalyzed by KF/Al2O3
Xiang‐Shan Wang,Da‐Qing Shi,Shu‐Jiang Tu. Michael‐Addition Reaction of Malononitrile with α,β‐Unsaturated Cycloketones Catalyzed by KF/Al2O3[J]. Chinese Journal of Chemistry, 2004, 22(2): 122-125. DOI: 10.1002/cjoc.20040220203
Authors:Xiang‐Shan Wang  Da‐Qing Shi  Shu‐Jiang Tu
Abstract:A series of KF/Al2O3 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‐4H‐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‐4H‐pyran derivatives was isolated successfully. The structures of the products were confirmed by X‐ray diffraction analysis.
Keywords:2‐amino‐3‐cyano‐4H‐pyran derivative  α,β‐unsaturated cycloketone  Michael‐addition reaction  synthesis
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