铜催化串联反应一锅合成吲哚螺四氢喹啉酮衍生物  

One-pot Synthesis of Indolspirotetrahydroquinolinone Derivatives Involving Copper-catalyzed Cascade Reaction

作　　者：钟雪 何菱[1] ZHONG Xue;HE Ling(West China School of Pharmacy,Sichuan University,Chengdu 610041,China)

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《合成化学》2023年第8期603-609,共7页Chinese Journal of Synthetic Chemistry

基　　金：川大-泸州战略合作项目(2017CDLZ-S34)。

摘　　要：吲哚螺四氢喹啉衍生物是生物活性小分子的重要结构单元,具有较大的成药潜力,但吲哚螺四氢喹啉的合成策略十分有限。以硝基取代的吲哚烷酮衍生物为底物,乙酰丙酮钼和三氟甲烷磺酸铜为催化剂,三苯基膦为还原剂,甲苯为溶剂,合成了新型吲哚螺四氢喹啉酮衍生物,其结构经^(1)HNMR,^(13)C NMR和HR-MS(ESI)表征。结果表明:该反应可能经过了硝基还原、氮宾插入和双键重排过程。Indolespirotetrahydroquinoline derivatives are important structural units of bioactive small molecules.It has great potential for proprietary medicine,but the synthesis strategy of indolespirotetrahydroquinoline is very limited.In this paper,novel indolespirotetrahydroquinolinone derivatives were synthesized using o-nitro-substituted indole alkanone derivatives as substrates,acetylacetone molybdenum and copper trifluoromethane sulfonate as catalysts,triphenylphosphine as reducing agent and toluene as solvent.Their structures were characterized by^(1)HNMR,^(13)C NMR and HR-MS(ESI).Based on the literature and experimental results,it is speculated that the reaction is a process in which nitro reduction,azane insertion,and double bond rearrangement.

关 键 词：吲哚螺四氢喹啉酮 吲哚烷酮 三苯基膦 乙酰丙酮钼 三氟甲烷磺酸铜 过渡金属催化合成 串联反应 

分 类 号：O621.3[理学—有机化学] O626[理学—化学]