摘要
酮亚胺具有良好的反应活性,在合成含氮的天然产物和药物分子中具有重要的作用,因此开发一种高效且简便的2-苯并噻吩N-Boc酮亚胺的合成策略是十分必要的。本文用苯并噻吩二酮为原料,通过经典的维蒂希反应,以21%~68%的收率首次合成了新型的2-苯并噻吩N-Boc酮亚胺产物(3a~3i),并拓展了9个不同取代基的底物。尝试了其在消旋磷酸催化下与吲哚的傅-克烷基化反应,成功构建了含有一个季碳中心的(2-(1H-吲哚-3-基)-5-甲基-3-氧代-2,3-二氢苯并噻吩-2-基)氨基甲酸叔丁酯(5),收率高达99%,并对这些化合物的结构进行了^(1)H NMR、^(13)C NMR和HR-MS(ESI-TOF)表征。
Ketimines have good reactivity and play an important role in the synthesis of nitrogencontaining natural products and drug molecules.Therefore,it is necessary to develop an efficient and simple strategy for the synthesis of 2-benzothiophene ketone imines.In this paper,nine novel tert-butyl(Z)-(3-oxobenzo[b]thiophen-2(3H)-ylidene)carbamates of benzothiophene ketones(3a~3i)were obtained in one step with a yield of 21%~68%using benzothiophene ketones as raw material through the classical Wittig reaction.The friedel-crafts alkylation reaction of the benzothiophene ketone with indole under the catalysis of racemic phosphoric acid was investigated,and the product containing a quaternary carbon center(5)was successfully constructed,yield of 99%.These products were characterized by^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).
作者
付晓慧
刘海辉
彭巧巧
陆纪宏
游勇
周鸣强
赵建强
葛真真
袁伟成
FU Xiaohui;LIU Haihui;PENG Qiaoqiao;LU Jihong;YOU Yong;ZHOU Mingqiang;ZHAO Jianqiang;GE Zhenzhen;YUAN Weicheng(National Engineering Research Center of Chiral Drugs,Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu 610041,China;Institute for Advanced Study,Chengdu University,Chengdu 610106,China;University of Chinese Academy of Sciences,Beijing 100049,China;Zhejiang Jinhua Conba Bio-Pharm.Co.,Ltd.,Jinhua 100038,China)
出处
《合成化学》
2025年第3期140-144,共5页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(22302021,22271027,22171029)
四川省科技厅项目(2024NSFSC0281)。
关键词
苯并噻吩酮亚胺
吲哚
维蒂希反应
合成
消旋磷酸
benzothiophene ketone
indole
Wittig reaction
synthesis
racemic phosphoric acid
