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Keywords = 1,2-benzoxaphosphorin

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6 pages, 1523 KB  
Short Note
3-((λ3-Oxidanylidene)(propylamino)methyl)-2-ethoxybenzo[e]-[1,2]oxaphosphinine-2-oxide
by Ana I. Koleva, Nevena I. Petkova-Yankova and Rositca D. Nikolova
Molbank 2024, 2024(3), M1870; https://doi.org/10.3390/M1870 - 19 Aug 2024
Viewed by 1367
Abstract
A method for the simple preparation of 2-ethoxy-N-propylbenzo[e][1,2]oxaphosphinine-3-carboxamide 2-oxide via an ultrasound technique using catalytic amounts of CuI is reported. The formation of the amide could indicate the isomerization of the formed E-alkene intermediate to its Z-form, assisted by the sonication [...] Read more.
A method for the simple preparation of 2-ethoxy-N-propylbenzo[e][1,2]oxaphosphinine-3-carboxamide 2-oxide via an ultrasound technique using catalytic amounts of CuI is reported. The formation of the amide could indicate the isomerization of the formed E-alkene intermediate to its Z-form, assisted by the sonication irradiation, and such transformation under the presented conditions has not been previously reported in the literature. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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34 pages, 14848 KB  
Article
Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
by Rumen Lyapchev, Ana I. Koleva, Iskra Z. Koleva, Kristian Subev, Ivelina Madzharova, Kristina B. Simeonova, Nevena Petkova-Yankova, Bernd Morgenstern, Vesela Lozanova, Petar Y. Petrov and Rositca D. Nikolova
Molecules 2022, 27(21), 7649; https://doi.org/10.3390/molecules27217649 - 7 Nov 2022
Cited by 8 | Viewed by 5221
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives II)
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38 pages, 11682 KB  
Review
Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds
by Ana I. Koleva, Nevena I. Petkova-Yankova and Rositca D. Nikolova
Molecules 2019, 24(11), 2030; https://doi.org/10.3390/molecules24112030 - 28 May 2019
Cited by 24 | Viewed by 6868
Abstract
Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation of dialkyl 2-oxo-2H-1-benzo- pyran-3-phosphonates and alkyl 1,2-benzoxaphosphorin-3-carboxylates. Their [...] Read more.
Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation of dialkyl 2-oxo-2H-1-benzo- pyran-3-phosphonates and alkyl 1,2-benzoxaphosphorin-3-carboxylates. Their chemical properties as acceptors in conjugate addition reactions, [2+2] and [3+2] cycloaddition reactions are discussed. Full article
(This article belongs to the Special Issue Coumarins and Coumarin Derivatives: From Chemistry to Drug)
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13 pages, 197 KB  
Article
Regio- and Stereoselective [2+2] Photodimerization of 3-Substituted 2-Alkoxy-2-oxo-2H-1,2-benzoxaphosphorines
by Rositca D. Nikolova, G. N. Vayssilov, Nestor Rodios and Anka Bojilova
Molecules 2002, 7(5), 420-432; https://doi.org/10.3390/70500420 - 31 May 2002
Cited by 32 | Viewed by 9484
Abstract
Diethyl 1,2-benzoxaphosphorine-3-carboxylates 5 undergo a regio- and stereoselective [2+2] photodimerization reaction in methanol solution under the action of sunlight, giving in all cases the corresponding anti head-to-tail dimers 6 and 7. Concerning the stereogenic P atom, the photodimerization is also stereoselective, and the [...] Read more.
Diethyl 1,2-benzoxaphosphorine-3-carboxylates 5 undergo a regio- and stereoselective [2+2] photodimerization reaction in methanol solution under the action of sunlight, giving in all cases the corresponding anti head-to-tail dimers 6 and 7. Concerning the stereogenic P atom, the photodimerization is also stereoselective, and the centrosymmetric stereoisomer 6 predominates over the non symmetric P-epimer 7. Full article
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