{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T17:01:32Z","timestamp":1790010092468,"version":"4.0.1"},"reference-count":72,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T00:00:00Z","timestamp":1789948800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["26-13-00010"],"award-info":[{"award-number":["26-13-00010"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]},{"award":["26-13-00010"],"award-info":[{"award-number":["26-13-00010"]}],"id":[{"id":"https:\/\/ror.org\/03y2gwe85","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Furan-2-yl substituted ethenes and conjugated butadienes containing two geminal electron-withdrawing groups, as well as phenylbutadienes with two electron acceptors, were synthesized from the corresponding aldehydes and various \u03b2-dicarbonyl compounds via aldol condensation. Reactions of these ethenylfurans and methyl 3-(benzofuran-2-yl)propenoate with arenes in triflic acid (TfOH) yield arylated 2,3-dihydrofurans and 2,3-dihydrobenzofurans, representing a novel synthetic approach to these dihydro derivatives. In contrast, analogous reactions of furanyl- and phenylbutadienes result in carbon\u2013carbon bond cleavage through retro-aldol and related acid-promoted processes. We propose plausible multistep mechanisms and cationic intermediates for these transformations. The synthesized furans and related compounds, at a concentration of 64 \u03bcg\/mL, exhibit moderate antimicrobial activity against the yeast-like fungus Candida albicans.<\/jats:p>","DOI":"10.3390\/molecules31183350","type":"journal-article","created":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T16:06:51Z","timestamp":1790006811000},"page":"3350","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of Furan and Benzene Derivatives Containing Unsaturated Substituents with Electron-Withdrawing Groups, and Analysis of Their Antimicrobial Activity"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4329-5131","authenticated-orcid":false,"given":"Mikhail V.","family":"Kalyaev","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7\/9, Saint Petersburg 199034, Russia"},{"name":"Department of General, Analytical and Applied Chemistry, Ufa State Petroleum Technical University, ul. Kosmonavtov 1, Ufa 450064, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"given":"Irina A.","family":"Boyarskaya","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7\/9, Saint Petersburg 199034, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4228-1248","authenticated-orcid":false,"given":"Alexander Yu.","family":"Ivanov","sequence":"additional","affiliation":[{"name":"Center for Magnetic Resonance, Research Park, Saint Petersburg State University, Universitetskiy pr., 26, Petrodvoretz, Saint Petersburg 198504, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2823-0986","authenticated-orcid":false,"given":"Dar\u2019ya V.","family":"Spiridonova","sequence":"additional","affiliation":[{"name":"Research Center for X-ray Diffraction Studies, Research Park, Saint Petersburg State University, Universitetskiy pr. 26, Petrodvoretz, Saint Petersburg 198504, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1571-6549","authenticated-orcid":false,"given":"Kristina E.","family":"Borovkova","sequence":"additional","affiliation":[{"name":"Research and Manufacturing Company \u00abHome of Pharmacy\u00bb, Zavodskaya st., 3-245, Kuzmolovskiy t.s., Leningrad Oblast, Saint Petersburg 188663, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sofia A.","family":"Brevnova","sequence":"additional","affiliation":[{"name":"Research and Manufacturing Company \u00abHome of Pharmacy\u00bb, Zavodskaya st., 3-245, Kuzmolovskiy t.s., Leningrad Oblast, Saint Petersburg 188663, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"given":"Artem O.","family":"Taraskin","sequence":"additional","affiliation":[{"name":"Research and Manufacturing Company \u00abHome of Pharmacy\u00bb, Zavodskaya st., 3-245, Kuzmolovskiy t.s., Leningrad Oblast, Saint Petersburg 188663, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"given":"Karina S.","family":"Gromozdova","sequence":"additional","affiliation":[{"name":"Research and Manufacturing Company \u00abHome of Pharmacy\u00bb, Zavodskaya st., 3-245, Kuzmolovskiy t.s., Leningrad Oblast, Saint Petersburg 188663, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"investigation","vocabulary":"credit"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3628-1492","authenticated-orcid":false,"given":"Aleksander V.","family":"Vasilyev","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7\/9, Saint Petersburg 199034, Russia"},{"name":"Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg 194021, Russia"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"conceptualization","vocabulary":"credit"},{"role":"methodology","vocabulary":"credit"},{"role":"supervision","vocabulary":"credit"},{"role":"writing-original-draft","vocabulary":"credit"},{"role":"writing-review-editing","vocabulary":"credit"}]}],"member":"1968","published-online":{"date-parts":[[2026,9,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Gandini, A., and Lacerda, T.M. 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