Screening of simple carbohydrates as a renewable organocatalyst for the efficient construction of 1,3-benzoxazine scaffold

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dc.authorid0000-0001-7228-2340en_US
dc.contributor.authorYıldırım A.
dc.contributor.authorKaya, Yunus
dc.contributor.authorGöker M.
dc.date.accessioned2022-01-11T05:56:40Z
dc.date.available2022-01-11T05:56:40Z
dc.date.issued2021en_US
dc.departmentBTÜ, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümüen_US
dc.description.abstractA convenient protocol for the two component preparation of 1,3-benzoxazines by using several protected and unprotected carbohydrate molecules as organocatalysts have been developed which is broadly applicable to condensation reaction between variety of Mannich bases and paraformaldehyde. This study revealed that fructose have much higher catalytic activity than the other carbohydrates and can be an alternative to metal-containing catalysts as a green renewable organocatalyst for efficient and rapid construction of 1,3-benzoxazine skeleton. In this context, 21 benzoxazine compounds were successfully synthesized and spectral characterizations of these compounds were carried out by spectroscopic methods and elemental analysis. Furthermore, density functional theory (DFT) calculations have been performed to study the detailed mechanism of organocatalyst assisted synthesis of the benzoxazine monomers. The results obtained from these calculations showed that the more realistic reaction pathway involves formation of a phenolate based intermediate which loses a water molecule to form benzenaminium ion. Subsequently, this ion provides the formation of the corresponding benzoxazines with good yields through the intramolecular ring closure step.en_US
dc.identifier.doi10.1016/j.carres.2021.108458en_US
dc.identifier.issn00086215
dc.identifier.scopusqualityN/Aen_US
dc.identifier.urihttps://hdl.handle.net/20.500.12885/1791
dc.identifier.volume510en_US
dc.identifier.wosqualityN/Aen_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.institutionauthorKaya, Yunus
dc.language.isoenen_US
dc.publisherElsevier Ltden_US
dc.relation.ispartofCarbohydrate Researchen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject1,3-Benzoxazinesen_US
dc.subjectCarbohydratesen_US
dc.subjectDFT studiesen_US
dc.subjectOrganocatalysisen_US
dc.subjectSustainable chemistryen_US
dc.titleScreening of simple carbohydrates as a renewable organocatalyst for the efficient construction of 1,3-benzoxazine scaffolden_US
dc.typeArticleen_US

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