Utilization of Water-Soluble Aminoethylamino-β-Cyclodextrin in the Pfitzinger Reaction-Catalyzed to the Synthesis of Diversely Functionalized Quinaldine.

In this study we describe the use of an aminoethylamino-β-cyclodextrin (AEA-β-CD) as a supramolecular homogeneous catalyst for the synthesis of a series of diversely substituted quinaldine derivatives which are medicinally important, via Pfitzinger reaction. This supramolecular catalyst exhibited remarkable catalytic activity with high substrate scope to achieve the synthetic targets in good to excellent yield, 69-92%. The structural and morphological properties of the synthesized AEA-β-CD were determined through MALDI-TOF mass spectrometry, NMR, FT-IR, and SEM analysis. Possible reaction mechanisms were determined through molecular host-guest complexation and proposed based on 2D NMR (ROESY) spectroscopy, FT-IR, FE-SEM, and DSC.