Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation
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Título: | Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation |
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Autor/es: | Gisbert, Patricia | Albert-Soriano, María | Pastor, Isidro M. |
Grupo/s de investigación o GITE: | Alternative Methodologies In Chemistry (AMIC) | Nuevos Materiales y Catalizadores (MATCAT) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Heterogeneous catalysis | Imidazolium salt | Nitrogen heterocycles | Sustainable chemistry | Synthetic methods |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 15-ago-2019 |
Editor: | Wiley-VCH Verlag GmbH & Co. KGaA |
Cita bibliográfica: | European Journal of Organic Chemistry. 2019, 30: 4928-4940. doi:10.1002/ejoc.201900880 |
Resumen: | Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2‐aminobenzaldehydes and 2‐aminoaryl ketones under solvent‐free conditions, employing 1,3‐bis(carboxymethyl)‐imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3‐acetylquinolines have been transformed, under solvent‐free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E‐factors are in the range of 14–23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described. |
Patrocinador/es: | This work was financially supported by the University of Alicante (VIGROB‐173, VIGROB‐285, and VIGROB‐316), the Spanish Ministerio de Economía y Competitividad (CTQ2015‐66624‐P, CTQ2017‐88171‐P), the Spanish Ministerio de Ciencia, Innovación y Universidades (PGC2018‐096616‐B‐I00) and the Generalitat Valenciana (AICO/2017/007). M. A.‐S. thanks the Spanish Ministerio de Educación, Cultura y Deporte for a predoctoral fellowship (FPU15/06040). P. G. thanks the ISO (University of Alicante) for a grant. |
URI: | http://hdl.handle.net/10045/95456 |
ISSN: | 1434-193X (Print) | 1099-0690 (Online) |
DOI: | 10.1002/ejoc.201900880 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1002/ejoc.201900880 |
Aparece en las colecciones: | INV - MATCAT - Artículos de Revistas INV - AMIC - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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2019_Gisbert_etal_EurJOC_final.pdf | Versión final (acceso restringido) | 1,63 MB | Adobe PDF | Abrir Solicitar una copia |
2019_Gisbert_etal_EurJOC_accepted.pdf | Accepted Manuscript (acceso abierto) | 1,59 MB | Adobe PDF | Abrir Vista previa |
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