Artículo
Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives
Fecha de publicación:
09/2023
Editorial:
American Chemical Society
Revista:
Journal of Organic Chemistry
ISSN:
0022-3263
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A protocol involving the irradiation of some 3-(2-alkenyl)estrone and 3-(2-alkenyl)-17-norestrone derivatives under a nitrogen atmosphere in organic solvents (both hexane and MeOH) followed by base-mediated intramolecular oxa-Michael cyclization reaction was investigated under steady-state conditions. The solvent effect and nature of the acyl group on the preparative photoreaction were studied and the multiplicity of the excited state was also demonstrated. The ortho-regioisomers were obtained in modest to good yields. Intramolecular based-mediate cyclization reaction of these synthons led to the formation of a set of novel substituted 4-chromanone moieties fused to estrone (and 17-norestrone) in good yields. This two-step sequential procedure involving a photochemical/intramolecular thermal cyclization strategy will be useful for the preparation of wide heterocyclic-fused-steroid compounds.
Palabras clave:
STEROIDS
,
PHOTO-FRIES
,
CHROMENONES
Archivos asociados
Licencia
Identificadores
Colecciones
Articulos(CIHIDECAR)
Articulos de CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Articulos de CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Citación
Quindt, Matías Iván; Gola, Gabriel Francisco; Ramirez, Javier Alberto; Bonesi, Sergio Mauricio; Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives; American Chemical Society; Journal of Organic Chemistry; 88; 19; 9-2023; 13796-13812
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