Gold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategy

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dc.contributor.authorTasdemir, Volkan
dc.contributor.authorMenges, Nurettin
dc.date.accessioned2024-02-23T13:59:41Z
dc.date.available2024-02-23T13:59:41Z
dc.date.issued2023
dc.departmentNEÜen_US
dc.description.abstractUnconjugated ynone derivatives with the 1,3-dicarbonyl structure are synthesized, and they are directly subjected to goldcatalyzed reaction with hydroxylamine without obtaining the oxime derivative. Among the different metal salts investigated, AuCl3 is the best for yielding and obtaining two different heterocyclic skeletons. Thanks to this reaction, two important heterocyclic molecules, 2H-1,2-oxazine and 1-hydroxypyrrole, are obtained as a one-pot and single-step strategy with favorable yields. Eleven different 2H-1,2-oxazine and 6 different 1-hydroxypyrrole derivatives are synthesized using starting compounds containing different substituents, in which steric hindrance and electronic effect are also taken into account. When the same reaction is carried out with the unconjugated ynone derivative containing only one carbonyl group, the only 1-hydroxypyrrole derivative is observed to be formed, and 1,2- oxazine ring is not observed.en_US
dc.description.sponsorshipTurkish Academy of Sciences Outstanding Young Scientist Award (TUBA-GEBIP); TUBAen_US
dc.description.sponsorshipThis study was supported by the Turkish Academy of Sciences Outstanding Young Scientist Award (TUBA-GEBIP). N.M. thanks TUBA for their financial support. The authors thank YYU Science and Application Center for NMR and HRMS spectra.en_US
dc.identifier.doi10.1007/s11696-023-03041-6
dc.identifier.endpage7992en_US
dc.identifier.issn0366-6352
dc.identifier.issn2585-7290
dc.identifier.issue12en_US
dc.identifier.scopus2-s2.0-85169322832en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage7985en_US
dc.identifier.urihttps://doi.org/10.1007/s11696-023-03041-6
dc.identifier.urihttps://hdl.handle.net/20.500.12452/11272
dc.identifier.volume77en_US
dc.identifier.wosWOS:001064901300002en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Int Publ Agen_US
dc.relation.ispartofChemical Papersen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAlkyne Cyclizationen_US
dc.subjectHomogen Catalysisen_US
dc.subjectHeterocyclic Chemistryen_US
dc.subjectOne-Pot Reactionen_US
dc.titleGold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategyen_US
dc.typeArticleen_US

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