Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 21, Issue 41, Pages 8372-8378Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob01461d
Keywords
-
Categories
Ask authors/readers for more resources
The study investigates the synthesis of nitrogen-containing aromatics through a Diels-Alder/aromatization cascade reaction using chitin-based furans. The results demonstrate that chitin-based 3-acetamido-furfural can be converted into di- and tri-substituted anilides with good to high yields via a hydrazone mediated reaction sequence.
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. A Diels-Alder/aromatization cascade reaction with chitin-based furans is a powerful tool for the synthesis of nitrogen-containing aromatics.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available