Effect of the nature of a fluorinated substituent on the synthesis of functionalized 1,3-diketones

Kudyakova, Yulia S.; Onoprienko, Aleksandra Ya.; Edilova, Yulia O.; Burgart, Ya. V.; Салоутин, В. И.; Bazhin, D. N.

doi:10.1007/s11172-021-3145-z

Cited by 7 publications

(4 citation statements)

References 37 publications

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“…Since sodium β-diketonates are highly soluble in organic solvents and water, we used a convenient method to isolate compound 1 . This procedure includes the formation of the copper(II) complex by adding Cu(OAc) 2 to the rection mixture and the further treatment of the Cu(II) chelate with Na 2 EDTA (disodium ethylenediamine tetraacetate) [ 75 ].…”

Section: Resultsmentioning

confidence: 99%

“…The literature provides scarce data on the synthesis and transformations of such triketones, in contrast to closely related class of 2,4-diketoesters [ 72 , 73 ]. Substantially more attention has been paid to the 1,2,4-triketone analogs, mainly fluorine-containing [ 74 , 75 , 76 , 77 , 78 ]. These compounds combine the reactivity of α-, β-, and γ-dicarbonyl systems, opening the route to a wider range of possible products via interaction with binucleophiles [ 79 ].…”

Section: Introductionmentioning

confidence: 99%

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Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Edilova,

Osipova,

Slepukhin

et al. 2023

IJMS

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A convenient approach to substituted pyrazoles and pyridazinones based on 1,2,4-triketones is presented. Chemo- and regiocontrol in condensations of t-Bu, Ph-, 2-thienyl-, and CO2Et-substituted 1,2,4-triketone analogs with hydrazines are described. The direction of preferential nucleophilic attack was shown to be switched depending on the substituent nature in triketone as well as the reaction conditions. The acid and temperature effects on the selectivity of condensations were revealed. Regiochemistry of heterocyclic core formation was confirmed by NMR and XRD studies. The facile construction of heterocyclic motifs bearing acetyl and (or) carbethoxy groups suggests them as promising mono- or bifunctional building blocks for subsequent transformations.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Edilova,

Osipova,

Slepukhin

et al. 2023

IJMS

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“…TML 2 complexes with L 1 and L 2 were courtesy of IOS UB RAS ( , accessed on 18 October 2022). The general procedures for the preparation of TML 2 have been described before [ 10 , 12 , 23 , 24 , 25 ]. For Ln(tmhd) 3 , the general method was used [ 17 ].…”

Section: Methodsmentioning

confidence: 99%

Structure and Properties of Heterometallics Based on Lanthanides and Transition Metals with Methoxy-β-Diketonates

et al. 2022

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The possibility of obtaining volatile polynuclear heterometallic complexes containing lanthanides and transition metals bound by methoxy-β-diketonates was studied. New compounds were prepared by cocrystallization of monometallic complexes from organic solvents. Ln(tmhd)3 were used as initial monometallic complexes (Ln = La, Pr, Sm, Gd, Tb, Dy, Lu; tmhd = 2,2,6,6-tetramethylheptane-3,5-dionate) in combination with TML2 in various ratios (TM = Cu, Co, Ni, Mn; L: L1 = 1,1,1-trifluoro-5,5-dimethoxypentane-2,4-dionate, L2 = 1,1,1-trifluoro-5,5-dimethoxy-hexane-2,4-dionate, L3 = 1,1,1-trifluoro-5-methoxy-5-methylhexane-2,4-dionate). Heterometallic complexes of the composition [(LnL2tmhd)2TM(tmhd)2] were isolated for light lanthanides Ln= La, Pr, Sm, Gd, and L= L1 or L2. By single crystal XRD, it has been established that heterometallic compounds containing La, Pr, Cu, Co, and Ni are isostructural linear coordination polymers of alternating mononuclear transition metal complexes and binuclear heteroleptic lanthanide complexes, connected by donor–acceptor interactions between oxygen atoms of the methoxy groups and transition metal atoms. A comparison of powder XRD patterns has shown that all heterometallic complexes obtained are isostructural. Havier lanthanides Ln = Tb, Dy, Lu did not form heterometallics. Instead, homometallic complexes Ln(L3)3 were identified for Ln = Dy, Lu as well as for Ln = La. The thermal properties of the complexes were investigated by TG-DTA and vacuum sublimation tests. The heterometallic complexes were found to be not volatile and decomposed under heating to produce inorganic composites of TM oxides and Ln fluorides. In contrast, Ln(L3)3 is volatile and may be sublimed in a vacuum. Results of magnetic measurements are discussed for several heterometallic and homometallic complexes.

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“…The Claisen condensation is known as the main synthetic method for the preparation of fluorinated β-diketones. The most frequently used condensing agents are NaH [31][32][33][34][35] and MeONa [36][37][38][39][40][41][42][43], while LiH [44][45][46][47][48], LDA [49] and Na [50] are less demanded. Ethers (DME, Et2O, THF) are more pre ferred solvents rather than benzene or alcohols.…”

Section: The Synthesis Of Fluorinated Ligands Containing the β-Dicarb...mentioning

confidence: 99%

Heterometallic Molecular Architectures Based on Fluorinated β-Diketone Ligands

et al. 2022

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This review summarizes the data on the synthesis of coordination compounds containing two or more different metal ions based on fluorinated β-diketonates. Heterometallic systems are of high interest in terms of their potential use in catalysis, medicine and diagnostics, as well as in the development of effective sensor devices and functional materials. Having a rich history in coordination chemistry, fluorinated β-diketones are well-known ligands generating a wide variety of heterometallic complexes. In this context, we focused on both the synthetic approaches to β-dicarbonyl ligands with additional coordination centers and their possible transformations in complexation reactions. The review describes bi- and polynuclear structures in which β-diketones are the key building blocks in the formation of a heterometallic framework, including the examples of both homo- and heteroleptic complexes.

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Effect of the nature of a fluorinated substituent on the synthesis of functionalized 1,3-diketones

Cited by 7 publications

References 37 publications

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Structure and Properties of Heterometallics Based on Lanthanides and Transition Metals with Methoxy-β-Diketonates

Heterometallic Molecular Architectures Based on Fluorinated β-Diketone Ligands

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