Synthesis of Fused Six-Membered Lactams to Isoxazole and Isoxazoline by Sequential Ugi Four-Component Reaction and Intramolecular Nitrile Oxide Cyclization

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dc.authoridGulten, Sirin/0000-0003-1735-0501
dc.contributor.authorGulten, Sirin
dc.date.accessioned2025-01-27T20:45:53Z
dc.date.available2025-01-27T20:45:53Z
dc.date.issued2020
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe advanced organic chemistry experiments describe the preparation of fused six-membered lactams to isoxazole and isoxazoline by employing Ugi four-component reaction (U-4CR) and intramolecular nitrile oxide cyclization (INOC) synthetic sequence. The experiments were carried out in 28 h (overnight for U-4CR) and 2 h (for INOC) using commercially available starting materials. The two-step reaction involves the in situ imine formation in the one-pot multicomponent reaction and in situ nitrile oxide formation in the INOC. The experiments are useful in the organic chemistry curriculum for the introduction of a onepot multicomponent reaction and 1,3-dipolar cycloaddition reactions.
dc.description.sponsorshipCanakkale Onsekiz Mart University Scientific Research Projects Coordination Department; BAP [2010/109]
dc.description.sponsorshipFinancial support for this project was provided by Canakkale Onsekiz Mart University Scientific Research Projects Coordination Department (Project No. BAP 2010/109). I thank NMR Analysis Laboratory of Hacettepe University, Central Laboratory of Pharmacy, Ankara University, for the measurement of the mass spectra, C comma anakkale Onsekiz Mart University, Science and Technology Research and Application Center (CcommaOBI.LTUM) for assistance with COSY-2D NMR spectra.
dc.identifier.doi10.1021/acs.jchemed.9b01169
dc.identifier.endpage3846
dc.identifier.issn0021-9584
dc.identifier.issn1938-1328
dc.identifier.issue10
dc.identifier.scopus2-s2.0-85091918353
dc.identifier.scopusqualityQ1
dc.identifier.startpage3839
dc.identifier.urihttps://doi.org/10.1021/acs.jchemed.9b01169
dc.identifier.urihttps://hdl.handle.net/20.500.12428/24751
dc.identifier.volume97
dc.identifier.wosWOS:000580953900050
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Chemical Education
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectUpper-Divison Undergraduate
dc.subjectLaboratory Instruction
dc.subjectOrganic Chemistry
dc.subjectHands-On Learning/Manipulatives
dc.subjectSynthesis
dc.subjectInquiry-Based/Discovery Learning
dc.subjectAmides
dc.subjectHeterocycles
dc.subjectNMR Spectroscopy
dc.subjectDiastereomers
dc.titleSynthesis of Fused Six-Membered Lactams to Isoxazole and Isoxazoline by Sequential Ugi Four-Component Reaction and Intramolecular Nitrile Oxide Cyclization
dc.typeArticle

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