1. Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
- Author
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Christopher J. Sumby, Trent D. Ashton, Samuel O. Nitschke, Shane M. Hickey, Douglas A. Brooks, Sally E. Plush, Martin J. Sweetman, Hickey, Shane M, Nitschke, Samuel O, Sweetman, Martin J, Sumby, Christopher J, Brooks, Douglas A, Plush, Sally E, and Ashton, Trent D
- Subjects
010405 organic chemistry ,Organic Chemistry ,010402 general chemistry ,Coumarin ,Umbelliferone ,01 natural sciences ,Fluorescence ,Combinatorial chemistry ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,cross-coupling reaction ,Amide ,Fluorescent materials ,auxochrome-based variations ,photophysical properties - Abstract
The Buchwald–Hartwig cross-coupling reaction between 4-methylumbelliferone-derived nonaflates with amides, carbamates, and sulfonamides is described. A wide variety of N-substituted 7-amino coumarin analogues was prepared in good to excellent yields. The photophysical properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H2O. We envisage that our reported protocol to access 7-amino-4-methylcoumarin derivatives will find use toward the development of new fluorescent coumarin-based probes by researchers in the field. usc Refereed/Peer-reviewed
- Published
- 2020