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Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

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 Sonogash...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9654183/
https://www.ncbi.nlm.nih.gov/pubmed/36364471
http://dx.doi.org/10.3390/molecules27217649
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author 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.
author_facet 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.
author_sort Lyapchev, Rumen
collection PubMed
description 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.
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spelling pubmed-96541832022-11-15 Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions 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. Molecules Article 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. MDPI 2022-11-07 /pmc/articles/PMC9654183/ /pubmed/36364471 http://dx.doi.org/10.3390/molecules27217649 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
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.
Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
title Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
title_full Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
title_fullStr Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
title_full_unstemmed Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
title_short Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
title_sort efficient synthesis of fluorescent coumarins and phosphorous-containing coumarin-type heterocycles via palladium catalyzed cross-coupling reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9654183/
https://www.ncbi.nlm.nih.gov/pubmed/36364471
http://dx.doi.org/10.3390/molecules27217649
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