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

Abstract

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.

Keywords

• Pseudo-eight-components reaction
• Meldrum’s acid
• Brønsted acidic ionic liquid
• Poly-substituted hydroquinolines
• Aldehydes