1,3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives

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dc.contributor.authorPolat-Cakir, Sidika
dc.date.accessioned2025-01-27T21:13:25Z
dc.date.available2025-01-27T21:13:25Z
dc.date.issued2020
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractNew phosphonate-containing five-membered heterocyclic dioxazole derivatives are synthesized via 1,3-dipolar cycloaddition reactions of nitrile oxides used as dipole with acyl phosphonates under basic conditions. Herein, acyl phosphonates take part in the cyclization process as a dipolarophile to afford the related dioxazole compounds in moderate-to-good yields (49-84%). Substituted aryl nitrile oxides and aroyl phosphonates were employed in the 1,3-dipolar cycloaddition reactions where triethylamine was the effective tertiary base. Alkyl version of acyl phosphonate also afforded the expected cycloadduct, that is, dimethyl 5-isopropyl-3-phenyl-1,4,2-dioxazol-5-yl-5-phosphonate. Diethyl/dimethyl 3,5-aryl-1,4,2-dioxazol-5-yl-5-phosphonate derivatives are fully characterized by using H-1 NMR, C-13 NMR, P-31-NMR, and FT along with high-resolution mass spectroscopy.
dc.description.sponsorshipCanakkale Onsekiz Mart University [FBA2020-3281]
dc.description.sponsorshipThis work was supported by Canakkale Onsekiz Mart University, the Scientific Research Coordination Unit (Project number: FBA2020-3281).
dc.identifier.doi10.1080/10426507.2020.1854259
dc.identifier.endpage467
dc.identifier.issn1042-6507
dc.identifier.issn1563-5325
dc.identifier.issue5
dc.identifier.scopus2-s2.0-85097159615
dc.identifier.scopusqualityQ3
dc.identifier.startpage461
dc.identifier.urihttps://doi.org/10.1080/10426507.2020.1854259
dc.identifier.urihttps://hdl.handle.net/20.500.12428/28412
dc.identifier.volume196
dc.identifier.wosWOS:000596653200001
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofPhosphorus Sulfur and Silicon and The Related Elements
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subject1
dc.subject3-Dipolar cycloaddition
dc.subjectacyl phosphonate
dc.subjectdioxazole
dc.subjectheterocyclic
dc.subjectdipole and dipolarophile
dc.title1,3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives
dc.typeArticle

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