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Cyclocondensation of coumarin-3-thioformates with 3-hydroxyoxindoles and 3-aminooxindoles for the synthesis of spiro-fused pentaheterocyclic compounds
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2019/12/23 , DOI: 10.1039/c9qo01039d
Chuan-Wen Lei 1, 2, 3, 4, 5 , Chuan-Bao Zhang 1, 2, 3, 4, 5 , Zhen-Hua Wang 5, 6, 7, 8 , Ke-Xin Xie 3, 5, 9, 10 , Jian-Qiang Zhao 5, 6, 7, 8 , Ming-Qiang Zhou 1, 2, 3, 4, 5 , Xiao-Mei Zhang 1, 2, 3, 4, 5 , Xiao-Ying Xu 1, 2, 3, 4, 5 , Wei-Cheng Yuan 1, 2, 3, 4, 5
Affiliation  

Coumarin-3-thioformates acting as a new type of 3-carbon partner were firstly prepared and engaged in reacting with 3-hydroxyoxindoles and 3-aminooxindoles by using DABCO or Et3N as the catalyst. A wide scope of structurally diverse spiro-fused pentaheterocyclic compounds including spiro-butyrolactoneoxindole[3,4-c]coumarins and spiro-butyrolactamoxindole[3,4-c]coumarins, which combined oxindole, dihydrofuranone or pyrrolidone, and coumarin in one molecule, could be smoothly obtained in high yields via a tandem Michael addition–lactonization/lactamization process under mild conditions.

中文翻译:

香豆素-3-硫代甲酸酯与3-羟基氧吲哚和3-氨基氧吲哚的环缩合反应用于合成螺环稠合的五杂环化合物

首先制备了作为新型的3-碳伙伴的香豆素-3-硫代甲酸酯,并通过使用DABCO或Et 3 N作为催化剂使其与3-羟基氧吲哚和3-氨基氧吲哚反应。多种结构多样的螺稠合五杂环化合物,包括螺-丁内酯-羟吲哚[3,4- c ]香豆素和螺-丁内酯-肟基吲哚[3,4- c ]香豆素,它们在一个分子中结合了吲哚,二氢呋喃酮或吡咯烷酮和香豆素,在温和条件下,可通过串联的迈克尔加成-内酰胺化/内酰胺化工艺顺利地以高收成率顺利获得。
更新日期:2020-02-13
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