HYDROARYLATION OF CARBON–CARBON DOUBLE BOND OF FURANIC CONJUGATED ENONES BY ARENES UNDER SUPERELECTROPHILIC ACTIVATION: SYNTHESIS AND EVALUATION OF ANTIMICROBIAL ACTIVITY OF NOVEL FURAN DERIVATIVES

Authors

  • Mikhail V. Kalyaev Department of Chemistry, Saint Petersburg State Forest Technical University, 5 Institutskiy pereulok, Saint Petersburg 194021, Russia Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034, Russia
  • Dmitry S. Ryabukhin Department of Chemistry, Saint Petersburg State Forest Technical University, 5 Institutskiy pereulok, Saint Petersburg 194021, Russia All-Russia Research Institute for Food Additives – Branch of V. M. Gorbatov Federal Research Center for Food Systems of Russian Academy of Sciences, 55 Liteyniy Ave., Saint Petersburg 191014, Russia
  • Alexander Yu. Ivanov Center for Magnetic Resonance, Research Park, Saint Petersburg State University, 26 Universitetskiy Ave., Saint Petersburg, Petrodvoretz 198504, Russia
  • Irina A. Boyarskaya Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034, Russia
  • Kristina Е. Borovkova Research and manufacturing company ''Home оf Pharmacy'', 3-245 Zavodskaya St., Kuzmolovskiy t.s., Leningrad oblast 188663, Russia
  • Lia R. Nikiforova Research and manufacturing company ''Home оf Pharmacy'', 3-245 Zavodskaya St., Kuzmolovskiy t.s., Leningrad oblast 188663, Russia
  • Julia V. Salmova Research and manufacturing company ''Home оf Pharmacy'', 3-245 Zavodskaya St., Kuzmolovskiy t.s., Leningrad oblast 188663, Russia
  • Artem O. Taraskin Research and manufacturing company ''Home оf Pharmacy'', 3-245 Zavodskaya St., Kuzmolovskiy t.s., Leningrad oblast 188663, Russia
  • Aleksandra M. Puzyk Center for X-Ray Diffraction Studies, Research Park, Saint Petersburg State University, 26 Universitetskiy Ave., Saint Petersburg, Petrodvoretz 198504, Russia
  • Aleksander V. Vasilyev Department of Chemistry, Saint Petersburg State Forest Technical University, 5 Institutskiy pereulok, Saint Petersburg 194021, Russia Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034, Russia

DOI:

https://doi.org/10.1007/7920

Keywords:

furans, furfural, carbocations, superelectrophilic activation, antimicrobial activity

Abstract

Various furanic conjugated enones, 4-(furan-2-yl)but-3-en-2-ones and 1-aryl-3-(furan-2-yl)prop-2-en-1-ones, have been synthesized from furfural, 5-hydroxymethylfurfural, and its derivatives by aldol condensation. It has been found for the first time, that reactions of these furanic conjugated enones with arenes under the action of triflic acid or AlCl3 afford the corresponding products of hydroarylation of the furan side chain carbon–carbon double bond in 29–89% yields. According to NMR study and DFT calculations, the corresponding O,C-diprotonated species of furanic enones are the reactive electrophilic intermediates. The obtained furan derivatives demonstrate moderate antimicrobial activity against yeast-like fungi Candida albicans at 64 μg/ml concentration. They also suppress Escherichia coli and Staphylococcus aureus.

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Published

2023-11-01

Issue

Vol. 59 No. 9/10 (2023)

Section

Original Papers