Bifunctional mesoporous MCF materials as catalysts in the Friedländer condensation

Abstract

We report herein the Friedländer reaction of 2-aminoaryl aldehydes 1 and ethyl acetatoacetate (2) affording the corresponding quinolines 3. The condensation selectively leads to quinolines 3 with good to excellent yields under mild reaction conditions. The first step of the condensation is the Knoevenagel reaction between reagents as experimentally confirmed. In addition, in order to justify our results we carried out a computational study based on DFT calculations analyzing this first step of the condensation. In this sense, we propose a cooperative catalysis mechanism involving the amine functions and metallic centers both of them acting as activating agents of the reagents and, therefore, favoring the process. © 2013 Elsevier B.V. All rights reserved.