N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights

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dc.contributor.authorZhu, Jie S.
dc.contributor.authorKraemer, Niklas
dc.contributor.authorShatskikh, Marina E.
dc.contributor.authorLi, Clarabella J.
dc.contributor.authorSon, Jung-Ho
dc.contributor.authorHaddadin, Makhluf J.
dc.contributor.authorTantillo, Dean Joseph
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.accessioned2025-01-24T11:22:00Z
dc.date.available2025-01-24T11:22:00Z
dc.date.issued2018
dc.description.abstractA concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2H-indazole synthesis, its reactivity was modulated for indazolone formation. © 2018 American Chemical Society.
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.8b01655
dc.identifier.eid2-s2.0-85051728195
dc.identifier.pmid30067041
dc.identifier.urihttp://hdl.handle.net/10938/25400
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofOrganic Letters
dc.sourceScopus
dc.subjectAmines
dc.subjectBenzyl alcohols
dc.subjectCatalysis
dc.subjectCyclization
dc.subjectIndazoles
dc.subjectNitroso compounds
dc.subjectOxidation-reduction
dc.subject2-nitrobenzyl alcohol
dc.subjectAmine
dc.subjectBenzyl alcohol derivative
dc.subjectIndazole derivative
dc.subjectNitroso derivative
dc.subjectChemistry
dc.subjectOxidation reduction reaction
dc.subjectSynthesis
dc.titleN-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
dc.typeArticle

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