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163 results on '"Matulis, Vadim E."'

1. Enantioselective Synthesis of Planar Chiral Ferrocene Triflones.

Author

Wen, Min, Erb, William, Mongin, Florence, Hurvois, Jean‐Pierre, Blot, Marielle, Roisnel, Thierry, Halauko, Yury S., Matulis, Vadim E., Koike, Yuta, Kitazawa, Yu, Kimura, Mutsumi, and Uchiyama, Masanobu

Subjects
AMIDES, TIME series analysis, CRYSTALLIZATION, CHELATES, CHIRALITY, FERROCENE
Abstract

A multi‐gram scale synthesis of ferrocenetriflone was optimised from ferrocenesulfonyl fluoride and Me3SiCF3 (Ruppert reagent). Enantioselective deprotolithiations were then optimised using alkyllithiums in the presence of catalytic (+)‐sparteine to afford 2‐substituted ferrocene triflones in 79–84% ee. The use of chiral lithium amides in the presence of in situ traps was also optimised and was found to outperform alkyllithium⋅chiral diamine chelates for the first time in the ferrocene series, with 89–93% ee. Crystallisation of derivatives afforded enantiopure compounds that were engaged in deprotolithiation‐electrophilic trapping sequences, a halogen 'dance' reaction and transition metal‐promoted coupling to afford a wide range of variously polysubstituted ferrocene triflones. [ABSTRACT FROM AUTHOR]

Published
2024
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2. Functionalisation of Chromane by Deprotonative Metallation.

Author

Bastien, Cléo, Erb, William, Halauko, Yury S., Matulis, Vadim E., Roisnel, Thierry, Sarazin, Yann, and Mongin, Florence

Subjects
ELECTROPHILES, TETRAHYDROFURAN, POTASSIUM, ACIDITY, HEXANE
Abstract

Despite the biological interest in chromane derivatives, few studies dedicated to the functionalisation of this heterocycle have been reported. Herein, our objective is to demonstrate the potential of alkali metal bases for the introduction of substituents at its positions 4 and 8, and to explain the observed reactivity based on quantum chemical calculations. Guided by these theoretical results, preliminary optimisation was carried out on 2,3‐dihydrobenzofuran before applying the optimal conditions to chromane. Deprotolithiation at C8 was thus achieved using n‐butyllithium in hexane at room temperature, while functionalisation at C4 was promoted by a 1:1 mixture of lithium 2,2,6,6‐tetramethylpiperidide and potassium tert‐butoxide in tetrahydrofuran at −50 °C. Various electrophiles were used to intercept the lithiated intermediates, providing a convenient access to substituted chromane derivatives. [ABSTRACT FROM AUTHOR]

Published
2024
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17. 2,6‐Di(1H‐tetrazol‐1‐yl)pyridine and its cupric chloride complex.

Author

Grigoryev, Evgeny Y., Grigorieva, Inna M., Lyakhov, Alexander S., Ivashkevich, Ludmila S., Matulis, Vadim E., Lavrenova, Ludmila G., Voitekhovich, Sergei V., and Grigoriev, Yuri V.

Subjects
CUPRIC chloride, MOLECULAR shapes, PYRIDINE, COORDINATION polymers, AMINO group, SINGLE crystals
Abstract

2,6‐Di(1H‐tetrazol‐1‐yl)pyridine (DTP) was prepared by a four‐stage procedure, including step‐by‐step heterocyclization of both amino groups of 2,6‐diaminopyridine with triethyl orthoformate and sodium azide. According to quantum‐chemical calculations and single crystal X‐ray diffraction data, DTP crystallizes in the form of the thermodynamically most stable conformer and has an almost flat molecular geometry. DTP was found to react with CuCl2 ⋅ 2H2O in ethanol to give the [Cu(DTP)Cl2(H2O)]n complex, which is a 1D coordination polymer, formed at the expense of bridging DTP ligand via the tetrazole ring nitrogen atoms N4. Possible coordination cites in DTP molecule are discussed using the data of quantum chemical calculations. The pyridine ring nitrogen atom of DTP does not participate in the formation of either coordination or intermolecular hydrogen bonds. This is explained by the results of quantum chemical calculations showing that this atom is less basic than N3 and N4 atoms of DTP molecule. [ABSTRACT FROM AUTHOR]

Published
2023
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18. Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties

Author

Ameur Messaoud, Mohamed Yacine Ameur, primary, Bentabed-Ababsa, Ghenia, additional, Fajloun, Ziad, additional, Hamze, Monzer, additional, Halauko, Yury S., additional, Ivashkevich, Oleg A., additional, Matulis, Vadim E., additional, Roisnel, Thierry, additional, Dorcet, Vincent, additional, and Mongin, Florence, additional

Published
2021
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36. Functionalization of Oxazolo[4,5-b]pyrazines by Deprotometallation

Author

Bisballe, Niels, Hedidi, Madani, Demmer, Charles S., Chevallier, Floris, Roisnel, Thierry, Dorcet, Vincent, Halauko, Yury S., Ivashkevich, Oleg A., Matulis, Vadim E., Bentabed-Ababsa, Ghenia, Bunch, Lennart, Mongin, Florence, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), University of Copenhagen = Københavns Universitet (UCPH), Université d'Oran 1 Ahmed Ben Bella [Oran], Belarusian State University, Fonds Europeen de Developpement Regional (FEDER) funds, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), and University of Copenhagen = Københavns Universitet (KU)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, Oxazolopyrazines, Acidity, Heterocycles, Synthesis design, Deprotometallation
Abstract

International audience; Different 2-arylated oxazolo[4,5-b]pyrazines, obtained by palladium(II)-catalyzed domino reaction from 2,3-dichloropyrazine and the corresponding carboxamides, were functionalized by deprotometallation. Employing lithium 2,2,6,6-tetramethylpiperidine, in order to form a lithio derivative, and then trapping it by iodolysis, proved to be inefficient. However, the presence of a zinc-based in situ trap allowed most substrates to be functionalized. Deprotonation of the pyrazine ring was observed in the presence of tolyl and anisyl groups at the oxazole 2-position. In contrast, with chlorophenyl and thienyl groups in this 2-position, deprotonation rather occurred on these groups either competitively or exclusively. The regioselectivities were discussed in the light of calculated pK(a) values of the substrates in THF. Finally, in the case of 2-phenyloxazolo[4,5-b]pyrazine, we converted the mixture of 5- and 6-iodinated products into the corresponding 5,6-diiodide, which was further functionalized by a double Suzuki coupling.

Published
2018
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37. On the N‐Arylation of Acetamide Using 2‐, 3‐ and 1'‐Substituted Iodoferrocenes.

Author

Kadari, Lingaswamy, Erb, William, Halauko, Yury S., Ivashkevich, Oleg A., Matulis, Vadim E., Lyakhov, Dmitry, Roisnel, Thierry, Radha Krishna, Palakodety, and Mongin, Florence

Subjects
ACETAMIDE, OXIDATIVE addition, DIOXANE, FERROCENE, COPPER, ACETAMIDE derivatives, AMIDES
Abstract

Various 2‐, 3‐ and 1'‐substituted iodoferrocenes were reacted with acetamide in the presence of copper(I) iodide (1 equiv), N,N'‐dimethylethylenediamine (1 equiv), tripotassium phosphate (2 equiv) in dioxane at 90 °C for 14 h, and allowed a large range of original 1,2‐, 1,3‐ and 1,1'‐disubstituted ferrocenes to be obtained. The results were compared as a function of the substituent and its position on the ring. DFT calculations revealed higher activation barrier for the oxidative addition in the ferrocene series when compared with classical planar aromatics. Structure‐property relationships were applied to rationalize the reactivity of the different iodoferrocenes. [ABSTRACT FROM AUTHOR]

Published
2021
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38. Fluoro- and Chloroferrocene: From 2- to 3-Substituted Derivatives

Author

Tazi, Mehdi, primary, Hedidi, Madani, additional, Erb, William, additional, Halauko, Yury S., additional, Ivashkevich, Oleg A., additional, Matulis, Vadim E., additional, Roisnel, Thierry, additional, Dorcet, Vincent, additional, Bentabed-Ababsa, Ghenia, additional, and Mongin, Florence, additional

Published
2018
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39. Functionalization of Oxazolo[4,5-b ]pyrazines by Deprotometallation

Author

Bisballe, Niels, primary, Hedidi, Madani, additional, Demmer, Charles S., additional, Chevallier, Floris, additional, Roisnel, Thierry, additional, Dorcet, Vincent, additional, Halauko, Yury S., additional, Ivashkevich, Oleg A., additional, Matulis, Vadim E., additional, Bentabed-Ababsa, Ghenia, additional, Bunch, Lennart, additional, and Mongin, Florence, additional

Published
2018
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41. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation withN-Arylation Reactions and Biological Properties

Author

Hedidi, Madani, primary, Maillard, Julien, additional, Erb, William, additional, Lassagne, Frédéric, additional, Halauko, Yury S., additional, Ivashkevich, Oleg A., additional, Matulis, Vadim E., additional, Roisnel, Thierry, additional, Dorcet, Vincent, additional, Hamzé, Monzer, additional, Fajloun, Ziad, additional, Baratte, Blandine, additional, Ruchaud, Sandrine, additional, Bach, Stéphane, additional, Bentabed-Ababsa, Ghenia, additional, and Mongin, Florence, additional

Published
2017
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42. From 2- to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen “Dance” to the Ferrocene Series

Author

Tazi, Mehdi, Erb, William, Halauko, Yury S., Ivashkevich, Oleg A., Matulis, Vadim E., Roisnel, Thierry, Dorcet, Vincent, and Mongin, Florence

Abstract

Two methods were compared to convert ferrocene into N,N-diisopropylferrocenecarboxamide, N,N-diethylferrocenecarboxamide, N,N-dimethylferrocenecarboxamide, and (4-morpholinocarbonyl)ferrocene, namely, deprotometalation followed by trapping using dialkylcarbamoyl chlorides and amide formation from the intermediate carboxylic acid. The four ferrocenecarboxamides were functionalized at C2; in the case of the less hindered and more sensitive amides, recourse to a mixed lithium–zinc 2,2,6,6-tetramethylpiperidino-based base allowed us to achieve the reactions. Halogen migration using lithium amides was next optimized. Whereas it appeared impossible to isolate the less hindered 3-iodoferrocenecarboxamides, 3-iodo-N,N-diisopropylferrocenecarboxamide proved stable and was converted to new 1,3-disubstituted ferrocenes by Suzuki coupling or amide reduction. DFT calculations were used to rationalize the results obtained.

Published
2024
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44. Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

Author

Messaoud, Mohamed Yacine Ameur, primary, Bentabed-Ababsa, Ghenia, additional, Hedidi, Madani, additional, Derdour, Aïcha, additional, Chevallier, Floris, additional, Halauko, Yury S, additional, Ivashkevich, Oleg A, additional, Matulis, Vadim E, additional, Picot, Laurent, additional, Thiéry, Valérie, additional, Roisnel, Thierry, additional, Dorcet, Vincent, additional, and Mongin, Florence, additional

Published
2015
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45. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N-Arylation Reactions and Biological Properties.

Author

Hedidi, Madani, Maillard, Julien, Erb, William, Lassagne, Frédéric, Halauko, Yury S., Ivashkevich, Oleg A., Matulis, Vadim E., Roisnel, Thierry, Dorcet, Vincent, Hamzé, Monzer, Fajloun, Ziad, Baratte, Blandine, Ruchaud, Sandrine, Bach, Stéphane, Bentabed‐Ababsa, Ghenia, and Mongin, Florence

Subjects
ARYLATION kinetics, REGIOSELECTIVITY (Chemistry), COPPER catalysts, BOND formation mechanism, QUINAZOLINE
Abstract

Various aromatic ketones were first functionalized next to the carbonyl function by deprotolithiation in the presence of a zinc salt followed by iodolysis. The outcome of the reactions was analyzed, and in particular their regioselectivity in the light of the calculated pKa values. Various halogenated ketones were next involved in copper-catalyzed twofold C-N bond formation to obtain fused systems based on 2-aminopyrimidines. Besides a potential antibacterial effect, 2-aminobenzothiopyrano[4,3,2-de]quinazoline was shown to inhibit PIM1 (IC50: 0.61 μM) and CDK2/cyclin A (IC50: 2.0 μM) kinases. [ABSTRACT FROM AUTHOR]

Published
2017
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46. Copper(ii) tetrafluoroborate complexes with the N3,N4-bridging coordination of 1-(tert-butyl)-1H-tetrazole: synthesis, crystal structure and magnetic properties

Author

Degtyarik, Mikhail M., primary, Lyakhov, Alexander S., additional, Ivashkevich, Ludmila S., additional, Matulis, Vitaly E., additional, Matulis, Vadim E., additional, Gruschinski, Sina, additional, Voitekhovich, Sergei V., additional, Kersting, Berthold, additional, and Ivashkevich, Oleg A., additional

Published
2015
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48. Deproto-metallation using mixed lithium–zinc and lithium–copper bases and computed CH acidity of 2-substituted quinolines

Author

Marquise, Nada, primary, Bretel, Guillaume, additional, Lassagne, Frédéric, additional, Chevallier, Floris, additional, Roisnel, Thierry, additional, Dorcet, Vincent, additional, Halauko, Yury S., additional, Ivashkevich, Oleg A., additional, Matulis, Vadim E., additional, Gros, Philippe C., additional, and Mongin, Florence, additional

Published
2014
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