无溶剂氧化亚锡催化合成2-[(3-吲哚基)-甲基]丙二酸二甲酯衍生物

doi:10.11944/j.issn.1000-0518.2015.07.140371

摘要/Abstract

摘要：

在氧化亚锡催化下,吲哚、醛和丙二酸二甲酯在无溶剂条件下三组分反应合成了10种2-[(3-吲哚基)-甲基]丙二酸二甲酯衍生物。反应无溶剂污染,反应条件温和,收率为58%~74%。讨论了反应速度与取代基的关系,探讨了可能的缩合反应机理,并应用¹H NMR、¹³C NMR、IR等技术手段确定了产品的结构。

关键词: (吲哚基)-甲基]丙二酸二甲酯, 丙二酸二甲酯, 硼酸, 醛, 无溶剂

Abstract:

Ten dimethyl 2-[(indol-3-yl)-methyl]malomate derivatives were synthesized by three-component one-pot reaction of indole with aldehydes and dimethyl malonate under solvent-free condition in the presence of SnO as the catalyst. The yields ranged from 58% to 74%. The advantages of this method are no solvent pollution and mild reaction conditions. Furthermore, a mechanism for this condensation reaction was proposed and the relationship between reaction rate and substituent groups was also studied. All the compounds synthesized were confirmed by ¹H NMR, ¹³C NMR and IR.

Key words: dimethyl [(indol-yl)-methyl]malonate, dimethyl malonate, SnO, aldehydes, solvent-free

中图分类号:

许招会. 无溶剂氧化亚锡催化合成2-[(3-吲哚基)-甲基]丙二酸二甲酯衍生物[J]. 应用化学, 2015, 32(7): 759-764.

XU Zhaohui. SnO Catalyzed Solvent-Free Synthesis of Dimethyl 2-[(Indol-3-yl)-methyl]malonate Derivatives[J]. Chinese Journal of Applied Chemistry, 2015, 32(7): 759-764.

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