Substituted anilides from chitin-based 3-acetamido-furfural

Cornelis van der Loo, Jeya Prathap Kaniraj, Ting Wang, Kees Pouwer, Onno Broekman, Mark Borst, André Heeres, Peter Deuss, Adriaan Minnaard

Onderzoeksoutput: ArticleAcademicpeer review

Samenvatting

The synthesis of aromatic compounds from biomass-derived furans is a key strategy in the pursuit of a sustainable economy. Within this field, a Diels–Alder/aromatization cascade reaction with chitin-based furans is emerging as a powerful tool for the synthesis of nitrogen-containing aromatics. In this study we present the conversion of chitin-based 3-acetamido-furfural (3A5F) into an array of di- and tri-substituted anilides in good to high yields (62–90%) via a hydrazone mediated Diels–Alder/aromatization sequence. The addition of acetic anhydride expands the dienophile scope and improves yields. Moreover, replacing the typically used dimethyl hydrazone with its pyrrolidine analogue, shortens reaction times and further increases yields. The hydrazone auxiliary is readily converted into either an aldehyde or a nitrile group, thereby providing a plethora of functionalized anilides. The developed procedure was also applied to 3-acetamido-5-acetylfuran (3A5AF) to successfully prepare a phthalimide.
Originele taal-2English
TijdschriftOrganic and Biomolecular Chemistry
DOI's
StatusPublished - 5 okt. 2023

Keywords

  • chitine
  • biobased
  • groene chemie
  • aniliden
  • furfural
  • aromatische verbindingen
  • aromaten

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