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Chemodivergent Conversion of Ketenimines Bearing Cyclic Dithioacetalic Units into Isoquinoline-1-thiones or Quinolin-4-ones as a Function of the Acetalic Ring Size

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dc.contributor.authorAlajarín, Mateo
dc.contributor.authorMarin-Luna, Marta
dc.contributor.authorSanchez-Andrada, Pilar
dc.contributor.authorVidal, Angel
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2021-02-04T17:29:21Z
dc.date.available2021-02-04T17:29:21Z
dc.date.created2019
dc.date.issued2019-06-21
dc.description.abstractC-Alkoxycarbonyl-C-phenyl-N-aryl ketenimines bearing 1,3-dithiolan-2-yl or 1,3-dithian-2-yl substituents at ortho position of the C-phenyl ring, respectively, transform into isoquino-line-1-thiones and quinolin-4-ones under thermal treatment in toluene solution. The formation of isoquinolinethiones involves a rare degradation of the 1,3-dithiolane ring, whereas, in contrast, the 1,3-dithiane ring remains intact during the reaction course leading to quinolin-4-ones. Computational density functional theory results support that the kinetically favorable mechanism for the formation of isoquinoline-l-thiones proceeds through a [1,5]-hydride shift/6 pi-electrocyclization cascade, followed by a thiirane extrusion process. Alternative mechanistic paths showing interesting electronic reorganization processes have been also scrutinized but resulted not competitive on energetic grounds.es
dc.formatapplication/pdfes
dc.format.extent18es
dc.identifier.citationJ. Org. Chem. 2019, 84, 8140–8150.
dc.identifier.doi10.1021/acs.joc.9b01014
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/10201/102641
dc.languageenges
dc.relation(I) Ministerio de Economía y Competitividad. Programa Estatal de Fomento de la Investigación Científica y Técnica de Excelencia. Proyectos I+D 2014 (Nacional). Nombre del proyecto: Funcionalidad y Síntesis de Moléculas Enlazadas Mecánicamente. Código: CTQ2014-56887-P. (II) Fundación Séneca (Comunidad Autónoma de la Región de Murcia). Ayudas para la realización de proyectos de investigación destinadas a grupos competitivos (Programa Séneca 2014) (Regional). Nombre del proyecto: Cicloadiciones de Ceteniminas Catalizadas por Metales de Transición y Reacciones de Ceteniminas con Carbenos Nucleofílicos y Bencino. Conmutación y Organización Tridimensional de Moléculas Entrelazadas. Código: 19240/PI/14.es
dc.relation.isreplacedbyhttps://doi.org/10.1021/acs.joc.9b01014es
dc.relation.publisherversionhttps://pubs.acs.org/doi/full/10.1021/acs.joc.9b01014es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectHYDROGEN-ATOM TRANSFERes
dc.subjectTHERMAL CYCLIZATIONes
dc.subjectTANDEM PROCESSESes
dc.subjectDFT CALCULATIONSes
dc.subjectHETEROCYCLESes
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleChemodivergent Conversion of Ketenimines Bearing Cyclic Dithioacetalic Units into Isoquinoline-1-thiones or Quinolin-4-ones as a Function of the Acetalic Ring Sizees
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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