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- Title
Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions.
- Authors
Lyapchev, Rumen; Koleva, Ana I.; Koleva, Iskra Z.; Subev, Kristian; Madzharova, Ivelina; Simeonova, Kristina B.; Petkova-Yankova, Nevena; Morgenstern, Bernd; Lozanova, Vesela; Petrov, Petar Y.; Nikolova, Rositca D.
- Abstract
Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position.
- Subjects
COUMARINS; PALLADIUM; HETEROCYCLIC compounds; OPTICAL properties; SONOGASHIRA reaction; SUZUKI reaction
- Publication
Molecules, 2022, Vol 27, Issue 21, p7649
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27217649