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3-乙烯基色酮、芳香醛和醋酸铵的一锅反应:一种高效合成高度官能化1,6-二氢吡啶衍生物的方法。

One-pot reaction of 3-vinylchromones, aromatic aldehydes, and ammonium acetate: an efficient approach to highly functionalized 1,6-dihydropyridine derivatives.

作者信息

Farajpour Behnaz, Kakaie Marzie, Hussain Faiq H S, Rakaee Fataneh, Moradkhani Fatemeh, Shiri Morteza

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Alzahra University Vanak Tehran 1993893973 Iran

Medical Analysis Department, Applied Science Faculty, Tishk International University Erbil 44001 Kurdistan Region Iraq.

出版信息

RSC Adv. 2025 Jan 27;15(4):2602-2607. doi: 10.1039/d4ra07863b. eCollection 2025 Jan 23.

Abstract

In this work, we present an efficient strategy for the straightforward synthesis of functionalized 1,6-dihydropyridine derivatives a three-component reaction of 3-vinylchromones, aromatic aldehydes, and ammonium acetate. A tandem procedure including NH aldimine formation/Michael-type addition/opening of the pyrone ring/isomerization/6π-electrocyclization/[1,5]-H shift allows rapid access to a series of dihydropyridines bearing an -hydroxybenzoyl and a benzoyl scaffold in good yields. Readily available precursors, simple heating conditions, and operational simplicity are some highlighted advantages of this transformation.

摘要

在本工作中,我们展示了一种高效策略,用于直接合成功能化的1,6 - 二氢吡啶衍生物——3 - 乙烯基色酮、芳香醛和醋酸铵的三组分反应。一个串联过程,包括亚胺形成/迈克尔型加成/吡喃酮环开环/异构化/6π - 电环化/[1,5] - H迁移,能够以良好的产率快速得到一系列带有 - 羟基苯甲酰基和苯甲酰基骨架的二氢吡啶。易于获得的前体、简单的加热条件和操作简便性是这种转化的一些突出优点。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cf8/11770593/0b81c36abaa2/d4ra07863b-f1.jpg

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