Light-Driven Catalyst-Free Access to Phthalazines: Entry to Antiviral Model Drugs by Merging Domino Reactions

0564609 - ÚOCHB 2024 RIV DE eng J - Článek v odborném periodiku
Guryev, A. - Schuster, F. - Herrmann, L. - Hahn, F. - Wangen, C. - Hodek, Jan - Weber, Jan - Marschall, M. - Tsogoeva, S. B.
Light-Driven Catalyst-Free Access to Phthalazines: Entry to Antiviral Model Drugs by Merging Domino Reactions.
European Journal of Organic Chemistry. Roč. 26, č. 5 (2023), č. článku e202200994. ISSN 1434-193X. E-ISSN 1099-0690
Grant CEP: GA MŠMT(CZ) EF16_019/0000729
Institucionální podpora: RVO:61388963
Klíčová slova: Diels-Alder reaction * light-driven domino reaction * one-pot reaction * photoenolization * phthalazines
Obor OECD: Virology
Impakt faktor: 2.8, rok: 2022
Způsob publikování: Open access
https://doi.org/10.1002/ejoc.202200994

We report the development of a metal-free four-step one-pot synthetic strategy to access high-value functionalized phthalazines using o-methyl benzophenones as starting compounds. Combining a light-mediated enolization of o-methyl benzophenones/Diels-Alder reaction domino process with a subsequent deprotection/aromatization domino reaction in one-pot leads to sustainable and efficient organic synthesis. The tangible advantages, i. e., absence of catalysts or additives, utilization of commercially available and/or easily accessible substrates, mild reaction conditions, simplicity, and single work-up procedure, make this combined process highly appealing for the direct construction of various 1-aryl-phthalazines. Importantly, in vitro bioactivity evaluation of these newly prepared heterocyclic compounds demonstrated a strong antiviral efficacy against major human pathogens like HCMV and SARS-CoV-2.
Trvalý link: https://hdl.handle.net/11104/0336273