Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

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dc.authoridDonmez, Selin Ezgi/0000-0002-1377-2689
dc.authoridBozkaya, Ugur/0000-0002-5203-2210
dc.authoridTurkmen, Yunus/0000-0002-9797-2820
dc.contributor.authorDonmez, Selin E.
dc.contributor.authorSoydas, Emine
dc.contributor.authorAydin, Gokcen
dc.contributor.authorSahin, Onur
dc.contributor.authorBozkaya, Ugur
dc.contributor.authorTurkmen, Yunus E.
dc.date.accessioned2025-03-23T19:35:52Z
dc.date.available2025-03-23T19:35:52Z
dc.date.issued2019
dc.departmentSinop Üniversitesi
dc.description.abstractA catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and alpha,beta-unsaturated acyl chlorides has been developed to access alpha-methylene-gamma-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 degrees C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the -TMS group in reducing the reaction barrier of the key cyclization step.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [116Z171, 116Z506]
dc.description.sponsorshipFinancial support from the Scientific and Technological Research Council of Turkey (TUBITAK; Grants Nos. 116Z171 and 116Z506) is gratefully acknowledged. We also acknowledge Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
dc.identifier.doi10.1021/acs.orglett.8b03886
dc.identifier.endpage558
dc.identifier.issn1523-7060
dc.identifier.issn1523-7052
dc.identifier.issue2
dc.identifier.pmid30985150
dc.identifier.scopus2-s2.0-85060037134
dc.identifier.scopusqualityQ1
dc.identifier.startpage554
dc.identifier.urihttps://doi.org/10.1021/acs.orglett.8b03886
dc.identifier.urihttps://hdl.handle.net/11486/5951
dc.identifier.volume21
dc.identifier.wosWOS:000456633000044
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofOrganic Letters
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectDirect Imine Acylation
dc.subjectOne-Pot
dc.subjectDiastereoselective Synthesis
dc.subjectHeterocyclic Chemistry
dc.subjectNitrogen-Heterocycles
dc.subjectSilicon
dc.subjectAccess
dc.subjectPhotocyclization
dc.subjectDiversity
dc.subjectThiourea
dc.titleAza-Nazarov Cyclization Reactions via Anion Exchange Catalysis
dc.typeArticle

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