Brønsted acidic ionic liquid catalyzed synthesis of poly-substituted hydroquinolines through diastereoselective, one-pot and pseudo-eight-component reaction

We have developed an efficient diastereoselective synthesis of poly-substituted hydroquinolines from commercially available starting materials, Meldrum’s acid, aromatic aldehydes and arylamines, in a simple and one-pot reaction using Brønsted acidic ionic liquid (4-sulfobutyl)-tris(4-sulfophenyl) ph...

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Detalles Bibliográficos
Autores: Salahi, Sajjad, Maghsoodlou, Malek Taher, Hazeri, Nourallah, Lashkari, Mojtaba, Akbarzadeh-Torbati, Niloufar, Kazemian, Mohammad Amin, García-Granda, Santiago, Torre-Fernández, Laura
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/359474
Acceso en línea:http://hdl.handle.net/10261/359474
Access Level:acceso abierto
Palabra clave:Pseudo-eight-components reaction
Meldrum’s acid
Brønsted acidic ionic liquid
Poly-substituted hydroquinolines
Aldehydes
Descripción
Sumario:We have developed an efficient diastereoselective synthesis of poly-substituted hydroquinolines from commercially available starting materials, Meldrum’s acid, aromatic aldehydes and arylamines, in a simple and one-pot reaction using Brønsted acidic ionic liquid (4-sulfobutyl)-tris(4-sulfophenyl) phosphonium hydrogen sulfate. These three materials react together through pseudo-eight-components reaction to generate complex products with four stereocenters that involves ten new bond formations. This synthetic method can be a combination of Knoevenagel and Michael reactions.