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Metal-free synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade michael addition / cyclization of methyl 4,4-difluorobut-2-ynoate with 2-aminobenzonitriles
Authors:Zhenhua Fan  Shanxue Yang  Xin Peng  Cheng Zhang  Jing Han  Jie Chen  Hongmei Deng  Min Shao  Hui Zhang  Weiguo Cao
Institution:1. Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai, 200444, PR China;2. Qianweichang College, Shanghai University, Shanghai, 200444, PR China;3. Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai, 200444, PR China;4. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, PR China;5. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, PR China
Abstract:A facile synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade Michael addition/cyclization between functionalized 2-aminobenzonitriles and methyl 4,4-difluorobut-2-ynoate has been developed. Various highly functionalized quinolines were assembled in moderate to good yields under mild metal-free reaction conditions.
Keywords:Quinoline  Difluoromethylation  Heterocycle synthesis
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