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. Thi...
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MDPI AG
2020-02-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/12/2/393 |
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doaj-a0d17d93d2e640a3a15b5f789932bb452020-11-25T01:40:00ZengMDPI AGPolymers2073-43602020-02-0112239310.3390/polym12020393polym12020393Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized QuinaldineYohan Kim0Vijay Vilas Shinde1Daham Jeong2Seunho Jung3Department of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, KoreaInstitute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, KoreaDepartment of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, KoreaDepartment of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, KoreaIn 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.https://www.mdpi.com/2073-4360/12/2/393aminoethylamino-β-cyclodextrinsupramolecular catalystpfitzinger reactionhost–guest complexation studyone-pot synthesis |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Yohan Kim Vijay Vilas Shinde Daham Jeong Seunho Jung |
| spellingShingle |
Yohan Kim Vijay Vilas Shinde Daham Jeong Seunho Jung Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine Polymers aminoethylamino-β-cyclodextrin supramolecular catalyst pfitzinger reaction host–guest complexation study one-pot synthesis |
| author_facet |
Yohan Kim Vijay Vilas Shinde Daham Jeong Seunho Jung |
| author_sort |
Yohan Kim |
| title |
Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine |
| title_short |
Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine |
| title_full |
Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine |
| title_fullStr |
Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine |
| title_full_unstemmed |
Utilization of Water-Soluble Aminoethylamino–β–Cyclodextrin in the Pfitzinger Reaction—Catalyzed to the Synthesis of Diversely Functionalized Quinaldine |
| title_sort |
utilization of water-soluble aminoethylamino–β–cyclodextrin in the pfitzinger reaction—catalyzed to the synthesis of diversely functionalized quinaldine |
| publisher |
MDPI AG |
| series |
Polymers |
| issn |
2073-4360 |
| publishDate |
2020-02-01 |
| description |
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. |
| topic |
aminoethylamino-β-cyclodextrin supramolecular catalyst pfitzinger reaction host–guest complexation study one-pot synthesis |
| url |
https://www.mdpi.com/2073-4360/12/2/393 |
| work_keys_str_mv |
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1725047800640569344 |