天然产物Tryptanthrin和Phaitanthrin A的全合成研究  

Total Synthesis of Tryptanthrin and Phaitanthrin A

作　　者：刘小卒[1] 杨思倚 Liu Xiaozu, Yang Siyi(Pharmacy School, Zunyi Medical University, Zunyi 563000, Chin)

机构地区：[1]遵义医学院药学院,贵州遵义563000

出　　处：《广东化工》2018年第13期284-285,共2页Guangdong Chemical Industry

摘　　要：以邻氨基苯甲酸为原料,通过酰氯化、与吲哚生成酰胺以及氢化还原合成了关环前体(2-氨基苯)(1H-吲哚)甲酮。以丙酮为溶剂,四丁基碘化铵为催化剂,过氧叔丁醇为氧化剂,冰醋酸为添加剂的条件下,(2-氨基苯)(1H-吲哚)甲酮发生串联反应生成色胺酮,收率为48%。在相同的反应体系下,在反应完成后,加入1M氢氧化钠溶液淬灭,一锅法合成天然产物Phaitanthrin A,收率42%。合成中间体以及目标产物经氢谱1H NMR鉴定。An amidation of indole with 2-nitrobcnzoyl chloride, generated from 2-nitrobenzoic acid via an acylating chlorination, occurred to produce the amide intermediate, which was then underwent a reductive process to afford the （2-aminophenyl）（1H-indoI-l-yl）methanone. Next, using aeetonitrile as the solvent, tetrabutyl ammonium iodide as the catalyst, tert-butyl alcohol as the oxidant, and glacial acetic acid as the additive, a cascade cyclization occurred to give tryptanthrin in 48 % yield. Furthermore, a one-pot synthesis of Phaitanthrin A was also accomplished in 42 % yield upon treating the resultant mixture with 1 M NaOH solution. The structures of synthetic intermediates and target molecules have been confirmed by 1H NMR.

关 键 词：色胺酮 天然产物全合成 串联反应 一锅煮反应 催化反应 

分 类 号：TQ[化学工程]