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Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
- Source :
- The Journal of organic chemistry. 85(12)
- Publication Year :
- 2020
-
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
- 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
Subjects
Details
- ISSN :
- 15206904
- Volume :
- 85
- Issue :
- 12
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....3389d6c0583387b9b0d71334a15c4816