Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

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Title: Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation
Authors: Gisbert, Patricia | Albert-Soriano, María | Pastor, Isidro M.
Research Group/s: Alternative Methodologies In Chemistry (AMIC) | Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Heterogeneous catalysis | Imidazolium salt | Nitrogen heterocycles | Sustainable chemistry | Synthetic methods
Knowledge Area: Química Orgánica
Issue Date: 15-Aug-2019
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2019, 30: 4928-4940. doi:10.1002/ejoc.201900880
Abstract: 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.
Sponsor: 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
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: https://doi.org/10.1002/ejoc.201900880
Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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