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

by Yohan Kim 1,†, Vijay Vilas Shinde 2,†, Daham Jeong 1 and Seunho Jung 1,2,*
1
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
2
Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Polymers 2020, 12(2), 393; https://doi.org/10.3390/polym12020393
Received: 14 November 2019 / Revised: 4 February 2020 / Accepted: 5 February 2020 / Published: 9 February 2020
(This article belongs to the Section Polymer Applications)
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. View Full-Text
Keywords: aminoethylamino-β-cyclodextrin; supramolecular catalyst; Pfitzinger reaction; host–guest complexation study; one-pot synthesis aminoethylamino-β-cyclodextrin; supramolecular catalyst; Pfitzinger reaction; host–guest complexation study; one-pot synthesis
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MDPI and ACS Style

Kim, Y.; Shinde, V.V.; Jeong, D.; Jung, S. Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine. Polymers 2020, 12, 393.

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