碱促进联烯酮与丙酮二羧酸酯反应制备 官能化的2-羟基间苯二甲酸酯

doi:10.11944/j.issn.1000-0518.2018.06.170214

摘要/Abstract

摘要：

发展了一种以碳酸钾为碱,在温和条件下,通过1,2-联烯酮与丙酮二羧酸二乙酯的串联反应高效合成取代2-羟基间苯二羧酸二乙酯类化合物的新方法。在最优条件下,以73%~85%的收率成功合成了一系列的目标产物。从机理上而言,该方法涉及了联烯酮与活泼亚甲基化合物的共轭Michael加成和酮的分子内羟醛缩合两个反应的串联组合。与文献方法相比,该方法还具有简单的起始原料,极高的反应产率和方便的处理过程等优点。

关键词: 羟基间苯二甲酸酯, 联烯酮, 丙酮二羧酸酯, 串联反应

Abstract:

A novel methodology for the synthesis of 2-hydroxyisophthalates through cascade reactions of 1,2-allenic ketones with ethyl acetonedicarboxylate using K₂CO₃ as the promoter under extremely mild conditions has been developed. Under optimal reaction conditions, a series of 2-hydroxyisophthalates derivatives were obtained with 73%~85% yield. The formation of the title compounds involves firstly a Michael addition of active methylene compounds and allenic ketone followed by its intramolecular condensation. Notable features of this protocol include simple starting materials, high yield, and easiness of handling.

Key words: hydroxyisophthalate, allenic ketones, acetonedicarboxylate, cascade reaction

王强,赵新萍. 碱促进联烯酮与丙酮二羧酸酯反应制备官能化的2-羟基间苯二甲酸酯[J]. 应用化学, 2018, 35(6): 645-651.

WANG Qiang,ZHAO Xinping. Synthesis of Functionalized 2-Hydroxyisophthalate via the Cascade Reactions of Allenic Ketones with Acetonedicarboxylate[J]. Chinese Journal of Applied Chemistry, 2018, 35(6): 645-651.

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