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

W. Fan 1 Y. Queneau 1 F. Popowycz 1
1 COB - Chimie Organique et Bioorganique
ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Abstract : 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 CH 2 OH motif found in HMF provides useful functionalization for the target molecules, which cannot be offered by simpler aldehydes such as furfural.
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W. Fan, Y. Queneau, F. Popowycz. HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction. Green Chemistry, Royal Society of Chemistry, 2018, 20 (2), pp.485-492. ⟨10.1039/c7gc03425c⟩. ⟨hal-02110673⟩

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