New strategies towards fine chemicals from HMF and GMF

Session: 
S3.4 Synthetic transformations
Code: 
OL3.4.2
Location (hall): 
Fucose
Start/end time: 
Monday, July 1, 2019 - 17:30 to 17:45
Yves
Queneau

Weigang Fan, Charlie Verrier, Lianjie Wang, Eman Dokmak, Sylvie Moebs, Mohammed Ahmar, Florence Popowycz, Yves Queneau1

1ICBMS, Univ Lyon,  INSA Lyon, UCBL, CNRS,  CPE, Villeurbanne, France

In the frame of our projects dedicated to biobased chemistry, we have studied several reactions using HMF or its glucosylated analog GMF as buiding blocks towards novel fine chemicals [1-4]. This communication gives an overview on our recent  in this field.  

For the MBH reaction, after a focus on biobased solvents [2], we have turned our attention to solventless conditions. We have also studied the multicomponent version of the aza-MBH reaction using GMF leading to novel α-amino-esters bearing a carbohydrate residue [3]. 

Considering the high synthetic interest of multicomponent reactions which give straightforward access to complex molecules [5], we have also investigated the Biginelli reaction, which involves a condensation of an aldehyde, a C–H acidic carbonyl compound and an urea leading to dihydropyrimidinones. We show that HMF sensitivity to acidic conditions can be overcome, reporting the first example of HMF in this process, with solvent-free reaction conditions [1]. 

The exploitation of 5-hydroxymethyl furfural (5-HMF) in aza-Piancatelli and Kabachnik-Fields reactions was also investigated, as well as dipolar cycloaddition of nitrones. Preliminary results on all these directions will be given, with examples of novel bio-based derivatives accessible by them.

Figure 1 : Various routes from HMF and GMF towards fine chemicals

References: 
  1. Fan, W. Queneau, Y. Popowycz, F. Green Chem. 2018, 20, 485-492.
  2. Tan, J.-N. Ahmar, M. Queneau, Y., RSC Adv. 2015, 5, 69238-69242.
  3. Tan, J.-N. Ahmar, M. Queneau, Y., Curr. Org. Synth. 2018, 15, 430-435.
  4. Verrier, C. Moebs-Sanchez, S. Queneau, Y. Popowycz, F., Org. Biomol. Chem. 2018, 16, 676-687.
  5. Fan, W. Queneau, Y. Popowycz, F., RSC Adv. 2018, 8, 31496-31501.

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