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

Guryev A, Schuster F, Herrmann L, Hahn F, Wangen C, Hodek J, Weber J, Marschall M, Tsogoeva S (2022)

Publication Type: Journal article

Publication year: 2022

Journal

DOI: 10.1002/ejoc.202200994

Abstract

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.

Authors with CRIS profile

Involved external institutions

Academy of Sciences of the Czech Republic (ASCR) / Akademie věd České republiky (AVČR) Czech Republic (CZ)

How to cite

APA:

Guryev, A., Schuster, F., Herrmann, L., Hahn, F., Wangen, C., Hodek, J.,... Tsogoeva, S. (2022). Light-Driven Catalyst-Free Access to Phthalazines: Entry to Antiviral Model Drugs by Merging Domino Reactions. European Journal of Organic Chemistry. https://dx.doi.org/10.1002/ejoc.202200994

MLA:

Guryev, Anton, et al. "Light-Driven Catalyst-Free Access to Phthalazines: Entry to Antiviral Model Drugs by Merging Domino Reactions." European Journal of Organic Chemistry (2022).

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