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Título
Enantioselective amination of 4-substituted pyrazolones catalyzed by oxindole-containing thioureas and by a recyclable linear-polymer-supported analogue in a continuous flow process
Autor
Año del Documento
2023
Editorial
American Chemical Society
Descripción
Producción Científica
Documento Fuente
The Journal Of Organic Chemistry, 2024, vol. 89, n.1, pp. 330-344
Résumé
A highly efficient organocatalytic amination of 4-substituted pyrazolones with azodicarboxylates mediated by a novel quinine-derived thiourea with a 3,3-diaryl-oxindole scaffold is reported. This synthetic method furnished 4-amino-5-pyrazolones in high yields and with excellent enantioselectivities (up to 97:3 er) at room temperature in short reaction times. Moreover, a linear-polymer-supported bifunctional thiourea, synthesized by reacting a bifunctional aromatic monomer (biphenyl) with isatin in superacidic media and further derivatization, was proven to be also an efficient heterogeneous organocatalyst for this α-amination reaction. The practical value of this process was demonstrated by the use of the immobilized catalyst in recycling experiments, maintaining the activity without additional reactivation, and in flow processes, allowing the synthesis of 4-amino-pyrazolone derivatives in a gram scale with high yield and enantioselectivity.
Materias (normalizadas)
Química orgánica
Polimeros y polimerización
Materias Unesco
2306 Química Orgánica
Palabras Clave
Aromatic compounds
Catalysts
Mixtures
Compuestos aromáticos
Catalizadores
Mezclas
ISSN
0022-3263
Revisión por pares
SI
Patrocinador
Agencia Estatal de Investigación- FEDER-UE (PID2020-118547GB-I00)
Junta de Castilla y León (VA224P20)
Junta de Castilla y León (VA224P20)
Version del Editor
Propietario de los Derechos
© 2023 The Authors
Idioma
eng
Tipo de versión
info:eu-repo/semantics/publishedVersion
Derechos
openAccess
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