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.
作者
刘小卒
杨思倚
Liu Xiaozu, Yang Siyi(Pharmacy School, Zunyi Medical University, Zunyi 563000, Chin)
出处
《广东化工》
CAS
2018年第13期284-285,共2页
Guangdong Chemical Industry
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
tryptanthrin
total synthcsis of natural products
cascade reactionr one-pot reaction
catalytic reation
