Davis–Beirut reaction inspired nitroso Diels–Alder reaction

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dc.contributor.authorSon, Jung-Ho
dc.contributor.authorCheung, Amy
dc.contributor.authorZhu, Jie S.
dc.contributor.authorHaddadin, Makhluf J.
dc.contributor.authorKurth, Mark J.
dc.contributor.departmentDepartment of Chemistry
dc.contributor.facultyFaculty of Arts and Sciences (FAS)
dc.contributor.institutionAmerican University of Beirut
dc.date.accessioned2025-01-24T11:22:20Z
dc.date.available2025-01-24T11:22:20Z
dc.date.issued2021
dc.description.abstractA Davis–Beirut reaction inspired nitroso Diels–Alder protocol is reported. The starting material for the procedure is a nitrophenyl moiety with the para position appropriately substituted with a 2°-amine (see 5) or 2°-alcohol (see 6). Deprotonation at the benzylic position followed by concomitant oxidation of the benzylic position and reduction of the nitro moiety delivers a nitrosophenyl intermediate, which subsequently undergoes a nitroso Diels–Alder reaction. This one-pot procedure delivers aryldihydro-1,2-oxazines in moderate yields. © 2021 Elsevier Ltd
dc.identifier.doihttps://doi.org/10.1016/j.tetlet.2021.152951
dc.identifier.eid2-s2.0-85102145499
dc.identifier.urihttp://hdl.handle.net/10938/25486
dc.language.isoen
dc.publisherElsevier Ltd
dc.relation.ispartofTetrahedron Letters
dc.sourceScopus
dc.subject1,2-oxazines
dc.subjectDavis-beirut reaction
dc.subjectNitroso diels-alder
dc.subjectNitrosobenzene
dc.subjectOne-pot protocol
dc.subject1,2 oxazine derivative
dc.subjectAlcohol
dc.subjectAmine
dc.subjectBenzene derivative
dc.subjectDihydro 1,2 oxazine derivative
dc.subjectNitrophenyl
dc.subjectNitroso derivative
dc.subjectUnclassified drug
dc.subjectArticle
dc.subjectChemical modification
dc.subjectChemical reaction
dc.subjectDavis beirut reaction
dc.subjectDeprotonation
dc.subjectDiels alder reaction
dc.subjectOne pot synthesis
dc.subjectOxidation
dc.subjectPhysical chemistry
dc.subjectReduction (chemistry)
dc.titleDavis–Beirut reaction inspired nitroso Diels–Alder reaction
dc.typeArticle

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