N-(苯并噻唑-2-基)亚胺与4-硝基-1-苯基丁-1-酮的aza-Henry/半缩酮胺化串联反应  

Aza-Henry/Hemiketamination Tandem Reactions of N-(Benzothiazol-2-yl)imines and 4-nitro-1-phenylbutan-1-one

作　　者：杜大明 郑瑶 DU Daming;ZHENG Yao(Key Laboratory of Medicinal Molecule Science&Pharmaceutical Engineering of Ministry of Industry and Information Technology,School of Chemistry and Chemical Engineering,Beijing Institute of Technology,Beijing 100081,China)

机构地区：[1]北京理工大学化学与化工学院医药分子科学与制剂工程工业和信息化部重点实验室,北京100081

出　　处：《北京理工大学学报》2025年第2期205-212,共8页Transactions of Beijing Institute of Technology

摘　　要：通过对近些年来文献的研究,发现对于使用N-(苯并噻唑-2-基)亚胺作为C2合成子的研究较少,因此探索以N-(苯并噻唑-2-基)亚胺作为C2合成子生成一系列杂环衍生物的新方法具有重要价值.成功设计通过aza-Henry/半缩酮胺化串联反应合成了一系列含有苯并噻唑骨架的N-(杂)芳基哌啶分子.即通过N-(苯并噻唑-2-基)亚胺与4-硝基-1-苯基丁-1-酮作为反应底物,在室温下以二氯甲烷为溶剂、三水合磷酸钾(10%mol)为催化剂,构建了一种合成N-(杂)芳基哌啶分子的有效方法,可以高收率和中等的立体选择性得到了一系列预期的产物.该串联反应在克级规模下仍然保持了良好的产率和立体选择性.There being relatively little study on C2 synthons with N-(benzothiazol-2-yl)imines in recent years,the new method study is important for C2 synthons to generate a series of heterocyclic derivatives based on N-(benzothiazol-2-yl)imines.In this paper,a series of N-(hetero)arylpiperidine molecules containing benzothiazole scaffolds were successfully designed and synthesized based on aza-Henry/hemiketamination tandem reaction.An effective method was constructed for synthesizing N-(hetero)arylpiperidine molecules making use of N-(benzothiazol-2-yl)imines and 4-nitro-1-phenylbutan-1-one as the reaction substrates,dichloromethane as the solvent,and potassium phosphate trihydrate(10%mol)as the catalyst at room temperature.Results show that a series of desired products can be obtained in high yield with moderate stereoselectivity,and the tandem reaction still can maintain a better yield and stereoselectivity at the gram-scale.

关 键 词：有机合成 串联反应 苯并噻唑 亚胺 4-硝基-1-苯基丁-1-酮 哌啶 

分 类 号：O621.3[理学—有机化学]