Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine
Yohan Kim,
Vijay Vilas Shinde,
Daham Jeong,
Seunho Jung
Affiliations
Yohan Kim
Department of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea
Vijay Vilas Shinde
Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea
Daham Jeong
Department of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea
Seunho Jung
Department of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea
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.