Preparation of 1,3-Disubstituted-5- cyano-4,5-dihydropyrazoles via 1,3-Dipolar Cycloaddition of Nitrile Imine with Acrylonitrile
Li-Ping Song
School of Chemistry and Pharmaceutics, East China University of Science and Technology, Shanghai 200237, China
Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorShi-Zheng Zhu
Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorJi-Ling Huang
School of Chemistry and Pharmaceutics, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorLi-Ping Song
School of Chemistry and Pharmaceutics, East China University of Science and Technology, Shanghai 200237, China
Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorShi-Zheng Zhu
Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorJi-Ling Huang
School of Chemistry and Pharmaceutics, East China University of Science and Technology, Shanghai 200237, China
Search for more papers by this authorAbstract
Oxidation of aldehyde 4-chloro-2, 3,5, 6-tetrafluorophenylhydrazones (1) with [bis(acetoxy)iodo] benzene leads to the formation of nitrile imines (2) which can react in situ with acrylonitrile to produce l-(4-chloro-2,3,5,6-tetrafluorophenyl)-3-substituted-5-cyano-4, 5-dihydropyrazoles (3) in moderate to good yields. The structures of new compounds were fully confirmed by their spectral data and elemental analyses. A plausible reaction mechanism for the generation of nitrile imine is proposed.
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