An Improved Synthesis of 3,6-Dihydro-<i>as</i>-indacene

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dc.contributor.authorRDibdalli, Yuvaraja
dc.contributor.authorFaundez, Rodrigo
dc.contributor.authorPreite, Marcelo
dc.contributor.authorMolins, Elies
dc.contributor.authorChavez, Ivonne
dc.contributor.authorAmshumali, Mungalimane K.
dc.contributor.authorMorales-Verdejo, Cesar
dc.contributor.authorManriquez, Juan M.
dc.date.accessioned2025-01-20T23:56:13Z
dc.date.available2025-01-20T23:56:13Z
dc.date.issued2021
dc.description.abstractThis contribution describes an updated synthetic route to 3,6-dihydro-as-indacene along with full characterization of all intermediates. The title compound is prepared by Mannich condensation of 2-methylfuran with formaldehyde and dimethylamine hydrochloride, quaternization of the resulting amine with methyl iodide, and conversion into the ammonium hydroxide salt by treatment with silver oxide in water. Subsequent Hoffmann elimination and [6,6]-cycloaddition through pyrolysis produces a furanocyclophane, which after photooxidation, intramolecular cycloaddition, and dehydration with sodium carbonate affords 2,3,6,7-tetrahydro-1,8-dione-as-indacene. Reduction of this diketone gives a mixture of alcohols, which after dehydration under slightly basic or acidic conditions produces 3,6-dihydro-as-indacene. The structure is confirmed by X-ray diffraction, and all intermediates are characterized by means of H-1 and C-13 NMR spectroscopy.
dc.fuente.origenWOS
dc.identifier.doi10.1055/s-0040-1707372
dc.identifier.eissn1437-210X
dc.identifier.issn0039-7881
dc.identifier.urihttps://doi.org/10.1055/s-0040-1707372
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/95139
dc.identifier.wosidWOS:000565246900001
dc.issue.numero3
dc.language.isoen
dc.pagina.final573
dc.pagina.inicio569
dc.revistaSynthesis-stuttgart
dc.rightsacceso restringido
dc.subjectas-indacene
dc.subject[6,6]-cycloaddition
dc.subjectpolycyclic bridged ligand
dc.subjectbimetallic ligand
dc.subjectMannich condensation
dc.subjectHoffmann elimination
dc.subject.ods12 Responsible Consumption and Production
dc.subject.odspa12 Producción y consumo responsable
dc.titleAn Improved Synthesis of 3,6-Dihydro-<i>as</i>-indacene
dc.typeartículo
dc.volumen53
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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