Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates.
作者： Xiaoqiong Diao , Yuji Wang , Yongwen Jiang , Dawei Ma
DOI: 10.1021/JO9017183
关键词: Catalysis 、 Medicinal chemistry 、 Acetanilide 、 Nitro compound 、 Ketone 、 Functional group 、 Chemistry 、 Nitro 、 Amination 、 Organic chemistry 、 Aqueous solution
摘要: CuI/l-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates affords the aryl amination products at room temperature, which undergo in situ additive cyclization under acidic conditions or heating to give substituted 1H-benzimidazoles 1,3-dihydrobenzimidazol-2-ones, respectively. A wide range functional groups including ketone, nitro, iodo, bromo, ester are tolerated these reaction conditions, providing heterocycles great diversity.
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