Dominique Vichard

Institut Lavoisier de Versailles

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i-10 index

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Co-Authors

François Terrier

Institut Lavoisier de Versailles

Gérard Jaouen

Centre National de la Recherche Scientifique

Michel Gruselle

Boehringer Ingelheim (France)

Hani Amouri

Centre National de la Recherche Scientifique

D. Riou

Centre National de la Recherche Scientifique

Marie‐José Pouet

Institut Lavoisier de Versailles

Régis Goumont

Institut Lavoisier de Versailles

F Belier

Institut Lavoisier de Versailles

Luke J. Alvey

Galapagos (France)

Taoufik Boubaker

University of Monastir

Cooperative Institutions

Centre National de la Recherche Scientifique

Institut Lavoisier de Versailles

Université Paris Cité

Sorbonne Université

Université de Versailles Saint-Quentin-en-Yvelines

Délégation Paris 5

Chimie ParisTech

Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques

Inserm

Sorbonne Paris Cité

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Inhibitory effects of a series of 7-substituted-indazoles toward nitric oxide synthases: Particular potency of 1H-indazole-7-carbonitrile

Bioorganic & Medicinal Chemistry (2008)

Betty Cottyn Francine Acher Booma Ramassamy Luke J. Alvey Michel Lepoivre

Indazole

Carboxamide

10.1016/j.bmc.2008.04.056

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Citations (17)

A New Cycloaddition Process Involving Nitro Group Participation in Polynitroaromatic Chemistry

The Journal of Organic Chemistry (1997)

Jean‐Claude Hallé Dominique Vichard Marie‐José Pouet François Terrier

The reaction of ethyl vinyl ether (2 equiv) with 4,6-dinitrobenzofuroxan (DNBF, 1 equiv) in dichloromethane affords a mixture of two diastereomeric dihydrooxazine N-oxide adducts, 5a and 5b, in a 4:1 ratio. Further addition of the enol reagent to this mixture results in a second cycloaddition process with formation of a bis(dihydrooxazine N-oxide) product 6, which can also be obtained directly upon treatment of DNBF with excess ethyl vinyl ether. The observed condensations are accounted for in terms of inverse electron demand Diels−Alder cycloaddition processes between the enol ether dienophile and the heterodienyl moieties of DNBF, constituted first, by the 6-NO2 group conjugated to the 6,7-double bond and then by the 4-NO2 group and the 4,5-double bond of the carbocyclic ring. The configurations of the cycloadducts 5a and 5b have been determined on the basis of collected 1H NMR parameters, as well as NOE experiments. It thus appears that the configuration of the major diastereomer corresponds to the endo product while that of the minor one corresponds to the exo product of the first cycloaddition process. The results obtained emphasize a low aromatic character for the DNBF molecule.

Diastereomer

Enol ether

10.1021/jo9704570

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Citations (54)

The versatile electrophilic reactivity of 4,6-dinitrobenzo[d]isoxazole-3-carbonitrile

Organic & Biomolecular Chemistry (2009)

Betty Cottyn A.M. Starosotnikov Dominique Vichard Régis Goumont С. А. Шевелев

The interaction of 4,6-dinitrobenzo[d]isoxazole-3-carbonitrile (5a) with methoxide ion has been kinetically investigated in methanol and a 20:80 (v/v) MeOH-Me2SO mixture. In methanol, stopped-flow experiments have revealed that a monomethoxyl σ-adduct (5a-Me) is first formed, resulting from a fast MeO− addition at the unsubstituted 7-carbon. Rate and equilibrium constants for this σ-complexation process could be determined, allowing a ranking of 5a within the pKa scale established for Meisenheimer electrophiles in methanol. With a pKa value of 13.50, the electrophilicity of 5a falls in the range of 1,3,6,8-tetranitronaphthalene, 2,4-dinitrothiophene or 4-nitrobenzofuroxan. This corresponds to a two-pKa units increase in electrophilicity from that of TNB, the common reference in σ-complex chemistry but it is notably below that of so-called superelectrophilic molecules like 4,6-dinitrobenzofuroxan. In addition to its ease of σ-complexation, 5a is found to undergo a slow but thermodynamically favourable addition of MeO− to the cyano group bonded to the isoxazole ring, leading to a complete conversion of the adduct 5a-Me into a dinitroimidate 6. The reactivity of 6 could be kinetically assessed. Going to 80% Me2SO still afforded initially the adduct 5a-Me but this anionic species undergoes addition of a second molecule of MeO− to the CN group, giving a dianion whose structure is unprecedented in the literature. Combining the above results with synthetic observations showing that 5a can readily contribute to SNAr reactions under appropriate experimental conditions emphasizes the multifaceted electrophilic reactivity of this electron-deficient heterocycle.

Isoxazole

Reactivity

Electrophilic substitution

Metalation

10.1039/b820256g

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Citations (11)

Intermolecular hydrogen bonding in organometallic-hormone derivatives. Crystal and molecular structures of .alpha.-[Cp*Ru(estradiol)][CF3SO3] and .alpha.-[Cp*Ru(3-O-(hydroxypropyl)estradiol)][CF3SO3]

Organometallics (1992)

Dominique Vichard Michel Gruselle Hani Amouri Gérard Jaouen Jacqueline Vaissermann

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIntermolecular hydrogen bonding in organometallic-hormone derivatives. Crystal and molecular structures of .alpha.-[Cp*Ru(estradiol)][CF3SO3] and .alpha.-[Cp*Ru(3-O-(hydroxypropyl)estradiol)][CF3SO3]Dominique Vichard, Michel Gruselle, Hani El Amouri, Gerard Jaouen, and Jacqueline VaissermannCite this: Organometallics 1992, 11, 2, 976–979Publication Date (Print):February 1, 1992Publication History Published online1 May 2002Published inissue 1 February 1992https://pubs.acs.org/doi/10.1021/om00038a075https://doi.org/10.1021/om00038a075research-articleACS PublicationsRequest reuse permissionsArticle Views70Altmetric-Citations22LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Alpha (finance)

10.1021/om00038a075

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Citations (25)

Reactions oft-BuOK and Dibenzyl, Benzyl Allyl, and Allyl β-Keto Sulfide Complexes of the Chiral Rhenium Lewis Acid [(η⁵-C₅H₅)Re(NO)(PPh₃)]⁺: Highly Diastereoselective or Chemoselective [2,3]-Sigmatropic Rearrangements

Organometallics (1996)

Phillip C. Cagle Oliver Meyer Dominique Vichard Konrad Weickhardt Atta M. Arif

Reaction of the dibenzyl sulfide complex [(η5-C5H5)Re(NO)(PPh3)(S(CH2Ph)2)]+TfO- (4a+TfO-) and t-BuOK (THF, −80 °C) gives the thiolate (η5-C5H5)Re(NO)(PPh3)(SCH(o-C6H4CH3)Ph) (5a; 99%) as a 96:4 mixture of SR,RS/SS,RR Re:C diastereomers. This transformation involves initial deprotonation of a benzyl group to give an ylide, followed by [2,3]- and [1,3]-rearrangements. A crystal structure of (SR,RS)-5a establishes the configuration. Similar reactions of the benzyl allyl sulfide complexes [(η5-C5H5)Re(NO)(PPh3)(S(CH2CRCH2)CH2Ph)]+TfO- (R = H, CH3) give mainly the thiolates (SS,RR)-(η5-C5H5)Re(NO)(PPh3)(SCH(CH2CRCH2)Ph), derived from benzyl group deprotonation. Some thiolates derived from allyl group deprotonation also form. Similar reactions of the allyl β-keto sulfide complexes [(η5-C5R5)Re(NO)(PPh3)(S(CH2CR'CR''2)CH2COPh)]+X- (R/R'/R'' = H/H/H, H/H/CH3, H/CH3/H, CH3/H/H) give the thiolates (η5-C5R5)Re(NO)(PPh3)(SCH(CR''2CR'CH2)COPh), derived from CH2COPh group deprotonation, as >96:<4 to 68:32 diastereomer mixtures. Reactions of 4a+TfO- with MeLi give mainly the [1,2]-rearrangement product (η5-C5H5)Re(NO)(PPh3)(SCH(CH2Ph)Ph) ((35−70):(65−30) diastereomer mixtures), which has been independently synthesized. The thiolate ligands are easily converted to free methyl sulfides. Mechanisms of diastereoselection, and similar reactions of organic sulfonium salts, are discussed.

Diastereomer

Ylide

10.1021/om950701i

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Citations (19)

Enantioselective syntheses of organosulfur compounds via [2,3] sigmatropic rearrangements of ylides derived from di(allyl), di(propargyl), and di(benzyl) sulfide complexes; Control of carbon configuration by an easily resolved and recycled rhenium auxiliary

Pure and Applied Chemistry (1996)

Oliver Meyer Phillip C. Cagle Konrad Weickhardt Dominique Vichard John A. Gladysz

Abstract

Propargyl

Organosulfur compounds

Carbon fibers

Sulfoxide

10.1351/pac199668010079

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Citations (28)

Assessing the Activating Effect of the (η⁵-C₅Me₅)Ru⁺ Group: A Kinetic and NMR Study of the Ionization of the (η⁶-Phenylnitromethane)- (η⁵-pentamethylcyclopentadienyl)ruthenium Cation in H₂O−Me₂SO Mixtures

Organometallics (1998)

Gilles Moutiers Audrey Peigneux Dominique Vichard François Terrier

Rates of proton abstraction from the (η6-phenylnitromethane)(η5-pentamethylcylopentadienyl)ruthenium cation (6) by a variety of bases B (OH-, carboxylate ions, primary and secondary amines) and of reprotonation of the resulting carbon base C-6 by the conjugate acids BH have been measured in a 50:50 (v/v) H2O−Me2SO mixture at 25 °C. The intrinsic reactivity of 6, as determined from the Brönsted plots for carboxylate ion or primary amine reactions is rather low: log = 0.6; log = 0.1. These values together with the pKa value for the ionization of 6 (pKa = 5.90) are typical for the formation of a nitronate-type carbon base, indicating that the RuCp*+-complexed phenyl ring is not capable of competing with the exocyclic nitro group in absorbing the negative charge generated by the ionization of 6. Additional evidence that the cation 6 ionizes to give a zwitterionic carbon base with an exocyclic nitronate functionality comes from the observation that C-6 undergoes instantaneous protonation at low pH (pH < 3) to give a nitronic acid. 1H and 13C NMR data collected for the ionization of 6 in 50:50 (v/v) H2O−Me2SO and pure Me2SO agree with the above conclusions. From a comparison of the behavior of 6 with that of (4-nitrophenyl)nitromethane, the inductive effect of a RuCp*+-coordinated phenyl ring is shown to be identical to that of a 4-nitrophenyl ring.

Carboxylate

Conjugate acid

Nitronate

Kinetic isotope effect

Base (topology)

Leaving group

Reactivity

10.1021/om9800905

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Citations (3)

Preferred antagonist binding state of the N-methyl-D-aspartate receptor: synthesis, pharmacology, and computer modeling of (phosphonomethyl)phenylalanine derivatives

Journal of Medicinal Chemistry (1992)

Agnes Dorville Isabelle McCort‐Tranchepain Dominique Vichard William A. Sather Rachid C. Maroun

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPreferred antagonist binding state of the N-methyl-D-aspartate receptor: synthesis, pharmacology, and computer modeling of (phosphonomethyl)phenylalanine derivativesAgnes Dorville, Isabelle McCort-Tranchepain, Dominique Vichard, William Sather, Rachid Maroun, Philippe Ascher, and Bernard P. RoquesCite this: J. Med. Chem. 1992, 35, 14, 2551–2562Publication Date (Print):July 1, 1992Publication History Published online1 May 2002Published inissue 1 July 1992https://doi.org/10.1021/jm00092a005RIGHTS & PERMISSIONSArticle Views442Altmetric-Citations15LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (2 MB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Icon

10.1021/jm00092a005

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Citations (19)

4-Chloro-7-nitrobenzofurazan as a Diels–Alder reagent. A facile access to highly functionalized naphthofurazans

Tetrahedron Letters (2001)

Dominique Vichard Luke J. Alvey François Terrier

Silyl enol ether

Pericyclic reaction

Diene

Reactivity

Diels–Alder reaction