{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T04:49:31Z","timestamp":1789966171831,"version":"4.0.1"},"reference-count":40,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,20]],"date-time":"2023-02-20T00:00:00Z","timestamp":1676851200000},"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":["21-13-00390"],"award-info":[{"award-number":["21-13-00390"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A new route to bicyclic \u03b3-lactams was found, which was proposed as a three-component cyclization of ethyl trifluoropyruvate with methyl ketones and 1,2-, 1,3-amino alcohols. As a result, a series of trifluoromethyl-substituted tetrahydropyrrolo [2,1-b]oxazol-5-ones and tetrahydropyrrolo[2,1-b][1,3]oxazine-6-ones was synthesized, in which the substituent at the nodal carbon atom was varied. The introduction of a twofold excess of ethyl trifluoropyruvate in reactions with amino alcohols and acetone made it possible to obtain the same bicycles, but functionalized with a hydroxyester fragment, which are formed due to four-component interactions of the reagents. Transformations with 2-butanone and aminoethanol lead predominantly to similar bicycles, while an analogous reaction with aminopropanol gives N-hydroxypropyl-2,3-dihydropyrrol-5-one. Almost all bicycles are formed as two diastereomers, the structure of which was determined using 1H, 19F, 13C NMR spectroscopy, including two-dimensional experiments and XRD analysis. A domino mechanism for the formation of tetrahydropyrrolo[2,1-b]oxazacycles was proposed, which was confirmed by their stepwise synthesis through the preliminary preparation of the aldol and bis-aldol from ethyl trifluoropyruvate and methyl ketones.<\/jats:p>","DOI":"10.3390\/molecules28041983","type":"journal-article","created":{"date-parts":[[2023,2,20]],"date-time":"2023-02-20T02:02:09Z","timestamp":1676858529000},"page":"1983","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Multicomponent Domino Cyclization of Ethyl Trifluoropyruvate with Methyl Ketones and Amino Alcohols as A New Way to \u03b3-Lactam Annulated Oxazacycles"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7853-688X","authenticated-orcid":false,"given":"Marina V.","family":"Goryaeva","sequence":"first","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olesya A.","family":"Fefelova","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanina V.","family":"Burgart","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marina A.","family":"Ezhikova","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mikhail I.","family":"Kodess","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pavel A.","family":"Slepukhin","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vasily S.","family":"Gaviko","sequence":"additional","affiliation":[{"name":"M.N. Mikheev Institute of Metal Physics, Ural Branch of the Russian Academy of Sciences (IMP UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1976-7861","authenticated-orcid":false,"given":"Victor I.","family":"Saloutin","sequence":"additional","affiliation":[{"name":"Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science (IOS UB RAS), Ekaterinburg 620108, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"10134","DOI":"10.1039\/C6OB01349J","article-title":"Biologically active \u03b3-lactams: Synthesis and natural sources","volume":"14","author":"Caruano","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Groaning, M.D., and Meyers, A.I. (2000). 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