Catalytic Conversion of Caffeine into Molecules of Valuable Interest Via N‐Demethylation Reaction

This work aims to apply catalytic processes to promote the conversion of caffeine into valuable dimethylxanthines via N‐demethylation reaction. Thus, we seek to evaluate the products formed and propose the reactions involved and their mechanisms. Reaction conditions were evaluated including differen...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2023-11, Vol.8 (43), p.n/a
Main Authors: Almeida, Flávio V. M., Diaz de Tuesta, Jose L., Gomes, Helder T., Guerreiro, Mário C.
Format: Article
Language:English
Subjects:
Ascorbic acid oxidation
Fenton
Nitrogen heterocycles
Radical reactions
Valorization
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Summary:This work aims to apply catalytic processes to promote the conversion of caffeine into valuable dimethylxanthines via N‐demethylation reaction. Thus, we seek to evaluate the products formed and propose the reactions involved and their mechanisms. Reaction conditions were evaluated including different concentrations of Fenton reagent and ascorbic acid to evaluate caffeine oxidation. Theobromine, paraxanthine, and theophylline formation was proven by HPLC‐DAD and mass spectrometry analysis evidencing the N‐demethylation reactions, via radicals, with about 1 % yield. These results open the way for new N‐demethylation reaction routes to be studied with applications for caffeine and other biomolecules in diverse areas such as biochemistry and medicinal chemistry. Application of the Fenton catalysis as alternative to promote the conversion of caffeine in other xanthines by N‐demethylation. In this scenario was verified the capability of ascorbic acid in promoting same reaction, both environmentally friendly processes. This work investigates the possibility of using a well known biocompound as a precursor to obtain value added molecules.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202301555