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A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction
Author(s) -
Schneider Rebekka V.,
Sehlinger Ansgar,
Meier Michael A. R.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002367
Subject(s) - chemistry , isocyanide , solubility , ugi reaction , amine gas treating , aldehyde , cyclodextrin , carbamate , alcohol , combinatorial chemistry , primary (astronomy) , organic chemistry , catalysis , physics , astronomy
Abstract Starch‐derived β‐cyclodextrins (β‐CDs) are used in pharmacy or the food and cosmetic industry as drug deliverers, separating agents, catalysts, detergents, or viscosity modifiers. However, solubility issues often restrict their potential applications. Here, we report a straightforward and direct one‐pot synthesis for the modification of β‐CDs based on the Ugi‐five‐component reaction (Ugi‐5CR). The Ugi‐5CR requires to react an amine, an aldehyde, an isocyanide, carbon dioxide and the β‐CD, which serves as alcohol component. Overall, five modified β‐CDs containing carbamate moieties were synthesized at room temperature in a high pressure reactor (10 bar) within 24 hours. The successful modifications are verified by mass spectrometry, nuclear magnetic resonance, and infrared spectroscopy, indicating one to three reacted primary hydroxyl groups per β‐CD. Additionally, we report altered solubility behavior of two of the five modified β‐CDs.