A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction. Issue 34 (10th September 2020)

• Record Type: Journal Article
• Authors: Schneider, Rebekka V.; Sehlinger, Ansgar; Meier, Michael A. R.
• Is Part Of: ChemistrySelect. Volume 5:Issue 34(2020)
• Page Start: 10765
• Page End: 10770
• Publication Date: 2020-09-10
• Subjects: β-cyclodextrin -- Ugi-five component reaction -- one-pot synthesis -- carbon dioxide -- solubility; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202002367
• Languages: English
• ISSNs: 2365-6549

Abstract

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. Abstract : Five novel modified β‐cyclodextrins were prepared via the Ugi‐five‐component reaction. The Ugi‐five‐component reaction is a simple one‐pot synthesis incorporating an aldehyde, isocyanide, amine, and carbon dioxide generating carbamate‐functionalized compounds. The carbamate‐functionalized cyclodextrins exhibit different solubility behavior compared to β‐cyclodextrin.