HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction,Green Chemistry

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HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction
Green Chemistry ( IF 9.3 ) Pub Date : 2017-12-11 00:00:00 , DOI: 10.1039/c7gc03425c
Weigang Fan _{1,

2,

3,

4,

5} , Yves Queneau _{1,

2,

3,

4,

5} , Florence Popowycz _{1,

2,

3,

4,

5}

Affiliation

The use of the renewable platform molecule 5-hydroxymethylfurfural (HMF) in the multi-component Biginelli reaction has been investigated. Multicomponent reactions (MCR) using HMF offer straightforward access to novel fine chemicals. However, the peculiar reactivity and lower stability of HMF have limited its use in such strategies. In this paper, we report our results on the use of HMF in 3-component Biginelli reactions, leading in one single step to a series of functionalized dihydropyrimidinones obtained in moderate to good yields, with a broad substrate scope of 1,3-dicarbonyl compounds and urea building blocks. This is the first report on the use of HMF in this reaction. The CH₂OH motif found in HMF provides useful functionalization for the target molecules, which cannot be offered by simpler aldehydes such as furfural.

中文翻译：

HMF在多组分反应中：在Biginelli反应中利用5-羟甲基糠醛（HMF）

研究了可再生平台分子5-羟甲基糠醛（HMF）在多组分Biginelli反应中的用途。使用HMF的多组分反应（MCR）可直接获得新型精细化学品。但是，HMF的特殊反应性和较低的稳定性限制了其在此类策略中的使用。在本文中，我们报告了我们在3组分Biginelli反应中使用HMF的结果，从而一步一步即可获得一系列以中等至良好收率获得的功能化二氢嘧啶酮，具有广泛的1,3-二羰基化合物底物范围和尿素构件。这是有关在此反应中使用HMF的第一份报告。CH ₂在HMF中发现的OH基序为目标分子提供了有用的功能化，而简单的醛类（例如糠醛）则无法提供。

更新日期：2018-01-22

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