A direct Diels–Alder reaction of chitin derived 3-acetamido-5-acetylfuran

Abstract

3A5AF, a biomass derived furan obtained from chitin, is used as a diene in the Diels–Alder reaction with maleimides. This allows the incorporation of bio-based nitrogen into the final products, a challenge unmet by commonly used furanics.

Nitrogenated Aromatics from Chitin.

“…In this case, the DA reaction was favoured by the dynamic trapping that led to the lactonization of the DA adducts, since the use of other acrylates (methyl acrylate or acrylic acid) failed to give the desired product. 15 We were also able to obtain the acetamino benzonitrile (12) through the reaction of 3A5EF with acrylonitrile. Despite the low yield for this reaction, the resulting compound presents a substitution pattern that is difficult to install through classic reactions involving aromatic compounds.…”

“…resulted in a drop in yield to 70% (Table 2, entry 10). Other acids such as TfOH, Amberlyst-15, p-TsOH and H2SO4-SiO2, were also tested, but there was no improvement in the yield (Table 2, entries [11][12][13][14].…”

Rapid access to molecular complexity from bioderived 5-HMF derivativesviacascade cycloadditions

“…11 In contrast, cycloaddition of biomass-derived 2,5-substituted furans, such as 5-HMF derivatives, represents a challenge. 12 The appearance of two substituents significantly changes the reactivity, affecting steric hindrance, the HOMO energy of the furan cycle, its electrostatic potential, and possibly influencing aromaticity. 13…”

Designed TiS2 nanosheets for efficient electrocatalytic reductive amination of biomass-derived furfurals

“…12,13 The selective synthesis of ONCs remains a big challenge due to the easily occurring side reactions. [14][15][16][17][18][19][20] Taking furanic aldehydes as an example, the amination reaction involves a complicated pathway as depicted in Scheme 1. The target ONC could be selectively generated from the condensation of furanic aldehydes (a) with ethanolamine through C-N coupling and then via the hydrogenation of the primary imine to the ONC.…”