Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid–base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H-chromenes
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Título: | Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid–base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H-chromenes |
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Autor/es: | Khazaee, Asma | Jahanshahi, Roya | Sobhani, Sara | Skibsted, Jørgen | Sansano, Jose M. |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Immobilized piperazine | Graphene oxide | Heterogeneous bifunctional acid–base catalyst | Multicomponent synthesis | 2-amino-3-cyano-4H-chromenes |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 22-jun-2020 |
Cita bibliográfica: | Green Chemistry. 2020, 22: 4604-4616. doi:10.1039/D0GC01274B |
Resumen: | Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid–base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C–H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles. |
Patrocinador/es: | Financial support for this project by the University of Birjand Research Council and access to the solid-state NMR facilities at the Department of Chemistry, Aarhus University and the XPS facilities of the University of Alicante are acknowledged. |
URI: | http://hdl.handle.net/10045/108201 |
ISSN: | 1463-9262 (Print) | 1463-9270 (Online) |
DOI: | 10.1039/D0GC01274B | 10.1039/D0GC01274B |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © The Royal Society of Chemistry 2020 |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1039/D0GC01274B |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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Khazaee_etal_2020_GreenChem_final.pdf | Versión final (acceso restringido) | 4,3 MB | Adobe PDF | Abrir Solicitar una copia |
Khazaee_etal_2020_GreenChem_accepted.pdf | Accepted Manuscript (acceso abierto) | 1,88 MB | Adobe PDF | Abrir Vista previa |
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