Relevant bibliographies by topics / Electrophilic nitrogens

Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Electrophilic nitrogens'

Author: Grafiati
Published: 27 February 2024

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Journal articles on the topic "Electrophilic nitrogens"

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Aeyad, Tahani, Jason Williams, Anthony Meijer, and Iain Coldham. "Lithiation–Substitution of N-Boc-2-phenylazepane." Synlett 28, no. 20 (August 17, 2017): 2765–68. http://dx.doi.org/10.1055/s-0036-1590857.

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Preparation of 2,2-disubstituted azepanes was accomplished from N-tert-butoxy(N-Boc)-2-phenylazepane by treatment with butyllithium then electrophilic quench. The lithiation was followed by in situ ReactIR spectroscopy and the rate of rotation of the carbamate was determined by variable temperature (VT)-NMR spectroscopy and by DFT studies. Most electrophiles add α to the nitrogen atom but cyanoformates and chloroformates gave ortho-substituted products. Cyclic carbamates were formed from an aldehyde or ketone electrophile. Kinetic resolution with sparteine was only poorly selective. Removal of the Boc group promoted cyclization to a homoindolizidine or an isoindolinone.
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LEVONEN, Anna-Liisa, Aimee LANDAR, Anup RAMACHANDRAN, Erin K. CEASER, Dale A. DICKINSON, Giuseppe ZANONI, Jason D. MORROW, and Victor M. DARLEY-USMAR. "Cellular mechanisms of redox cell signalling: role of cysteine modification in controlling antioxidant defences in response to electrophilic lipid oxidation products." Biochemical Journal 378, no. 2 (March 1, 2004): 373–82. http://dx.doi.org/10.1042/bj20031049.

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The molecular mechanisms through which oxidized lipids and their electrophilic decomposition products mediate redox cell signalling is not well understood and may involve direct modification of signal-transduction proteins or the secondary production of reactive oxygen or nitrogen species in the cell. Critical in the adaptation of cells to oxidative stress, including exposure to subtoxic concentrations of oxidized lipids, is the transcriptional regulation of antioxidant enzymes, many of which are controlled by antioxidant-responsive elements (AREs), also known as electrophile-responsive elements. The central regulator of the ARE response is the transcription factor Nrf2 (NF-E2-related factor 2), which on stimulation dissociates from its cytoplasmic inhibitor Keap1, translocates to the nucleus and transactivates ARE-dependent genes. We hypothesized that electrophilic lipids are capable of activating ARE through thiol modification of Keap1 and we have tested this concept in an intact cell system using induction of glutathione synthesis by the cyclopentenone prostaglandin, 15-deoxy-Δ12,14-prostaglandin J2. On exposure to 15-deoxy-Δ12,14-prostaglandin J2, the dissociation of Nrf2 from Keap1 occurred and this was dependent on the modification of thiols in Keap1. This mechanism appears to encompass other electrophilic lipids, since 15-A2t-isoprostane and the lipid aldehyde 4-hydroxynonenal were also shown to modify Keap1 and activate ARE. We propose that activation of ARE through this mechanism will have a major impact on inflammatory situations such as atherosclerosis, in which both enzymic as well as non-enzymic formation of electrophilic lipid oxidation products are increased.
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Ceaser, E. K., D. R. Moellering, S. Shiva, A. Ramachandran, A. Landar, A. Venkartraman, J. Crawford, et al. "Mechanisms of signal transduction mediated by oxidized lipids: the role of the electrophile-responsive proteome." Biochemical Society Transactions 32, no. 1 (February 1, 2004): 151–55. http://dx.doi.org/10.1042/bst0320151.

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Cellular redox signalling is mediated by the post-translational modification of proteins by reactive oxygen/nitrogen species or the products derived from their reactions. In the case of oxidized lipids, several receptor-dependent and -independent mechanisms are now emerging. At low concentrations, adaptation to oxidative stress in the vasculature appears to be mediated by induction of antioxidant defences, including the synthesis of the intracellular antioxidant glutathione. At high concentrations apoptosis occurs through mechanisms that have yet to be defined in detail. Recent studies have revealed a mechanism through which electrophilic lipids, formed as the reaction products of oxidation, orchestrate these adaptive responses in the vasculature. Using a proteomics approach, we have identified a subset of proteins in cells that we term the electrophile-responsive proteome. Electrophilic modification of thiol groups in these proteins can initiate cell signalling events through the transcriptional activation of genes regulated by consensus sequences for the antioxidant response element found in their promoter regions. The insights gained from our understanding of the biology of these mechanisms will be discussed in the context of cardiovascular disease.
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Palillero-Cisneros, Angel, Paola G. Gordillo-Guerra, Fernando García-Alvarez, Olivier Jackowski, Franck Ferreira, Fabrice Chemla, Joel L. Terán, and Alejandro Perez-Luna. "α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping." Beilstein Journal of Organic Chemistry 19 (September 21, 2023): 1443–51. http://dx.doi.org/10.3762/bjoc.19.103.

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We demonstrate that α-(aminomethyl)acrylates are suitable acceptors for 1,4-additions of dialkylzincs in aerobic conditions. The air-promoted radical–polar crossover process involves the 1,4-addition of an alkyl radical followed by homolytic substitution at the zinc atom of dialkylzinc. Coordination of the nitrogen atom to zinc enables this SH2 process which represents a rare example of alkylzinc-group transfer to a tertiary α-carbonyl radical. The zinc enolate thus formed readily undergoes β-fragmentation unless it is trapped by electrophiles in situ. Enolates of substrates having free N–H bonds undergo protodemetalation to provide ultimately the 1,4-addition adduct. In the presence of carbonyl acceptors, aldol condensation occurs providing overall a tandem 1,4-addition–aldol process. When a tert-butanesulfinyl moiety is present on the nitrogen atom, these electrophilic substitution reactions occur with good levels of chiral induction, paving the way to enantioenriched β2-amino acids and β2,2-amino acids.
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Cao, Chengyao, Jinyu Sheng, and Chao Chen. "Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles." Synthesis 49, no. 23 (October 11, 2017): 5081–92. http://dx.doi.org/10.1055/s-0036-1589515.

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Developing versatile methodologies to construct various nitrogen­-containing heterocycles is a crucially significant part of contemporary organic chemistry. This review summarizes recent developments on the formation of nitrogen-containing heterocycles triggered by diaryliodonium salts. Diaryliodonium salts, as electrophilic arylating agents in the presence of catalytic copper salts, can react with nitriles to give N-arylnitrilium cations, which are highly reactive species. These species can efficiently react with nucleophiles, including C-, N- and O-nucleophiles, to give the corresponding products. This strategy is not only efficient and convenient, but also enables the synthesis of diverse nitrogen-containing heterocycles such as quinolines, quinazolines, and phenanthridines.1 Introduction2 Strategies and Mechanisms3 Cascade Annulations3.1 Cascade Annulation of Diaryliodoniums, Nitriles and C-Nucleo­philes3.2 Cascade Annulation of Diaryliodoniums, Nitriles and N-Nucleo­philes3.3 Cascade Annulation of Diaryliodoniums, Nitriles and O-Nucleo­philes4 Summary and Outlook
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Slivka, Mikhailo, and Mikhailo Onysko. "The Use of Electrophilic Cyclization for the Preparation of Condensed Heterocycles." Synthesis 53, no. 19 (May 19, 2021): 3497–512. http://dx.doi.org/10.1055/s-0040-1706036.

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AbstractCondensed heterocycles are well-known for their excellent biological effects and they are undeniably important compounds in organic chemistry. Electrophilic cyclization reactions are widely used for the synthesis of mono-heterocyclic compounds. This review highlights the utility of electrophilic cyclization reactions as an effective generic tool for the synthesis of various condensed heterocycles containing functional groups that are able to undergo further chemical transformations, such as nucleophilic substitution, elimination, re-cyclization, cleavage, etc. This review describes the reactions of unsaturated derivatives of different heterocycles with various electrophilic agents (halogens, arylsulfanyl chlorides, mineral acids) resulting in annulation of an additional partially saturated heterocycle. The electrophilic reaction conditions, plausible mechanisms and the use of such transformations in organic synthesis are also discussed. The review mainly focuses on research published since 2002 in order to establish the current state of the art in this area. 1 Introduction2 Electrophilic Cyclization Pathways Involving a Nitrogen Nucleo­philic Center3 Electrophilic Cyclization Pathways Involving a Chalcogen Nucleophilic Center3.1 Sulfur Centers3.2 Oxygen Centers3.3 Selenium Centers4 Strategies and Mechanisms5 Conclusion
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Chandra, Swaroop, B. Suryaprasad, N. Ramanathan, and K. Sundararajan. "Nitrogen as a pnicogen?: evidence for π-hole driven novel pnicogen bonding interactions in nitromethane–ammonia aggregates using matrix isolation infrared spectroscopy and ab initio computations." Physical Chemistry Chemical Physics 23, no. 10 (2021): 6286–97. http://dx.doi.org/10.1039/d0cp06273a.

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Bhadra, Biswa Nath, Yong Su Baek, Cheol Ho Choi, and Sung Hwa Jhung. "How neutral nitrogen-containing compounds are oxidized in oxidative-denitrogenation of liquid fuel with TiO2@carbon." Physical Chemistry Chemical Physics 23, no. 14 (2021): 8368–74. http://dx.doi.org/10.1039/d1cp00633a.

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In oxidative denitrogenation of neutral nitrogen-containing compounds, it was found that oxygen firstly attacks the nitrogen atom, via electrophilic addition of an active oxygen atom; and oxygen on nitrogen moves to the nearby carbon atom because of the relative stability of the intermediates and products.
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Ageshina, Alexandra A., Gleb A. Chesnokov, Maxim A. Topchiy, Igor V. Alabugin, Mikhail S. Nechaev, and Andrey F. Asachenko. "Making endo-cyclizations favorable again: a conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides." Organic & Biomolecular Chemistry 17, no. 18 (2019): 4523–34. http://dx.doi.org/10.1039/c9ob00615j.

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Shen, Kun, and Qiu Wang. "Copper-catalyzed diamination of unactivated alkenes with hydroxylamines." Chemical Science 6, no. 7 (2015): 4279–83. http://dx.doi.org/10.1039/c5sc00897b.

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Dissertations / Theses on the topic "Electrophilic nitrogens"

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Blanc, Sylvain. "New reagents for asymmetric electrophilic nitrogen transfer." Thesis, Loughborough University, 2004. https://dspace.lboro.ac.uk/2134/34126.

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This thesis describes the synthesis of new chiral NH oxaziridines and their uses for electrophilic amination reactions. The introduction highlights some of the most successful electrophilic amination reagents and development of systems for the formation of carbon-nitrogen bonds. Examples of the use of camphor and fenchone NH-oxaziridines synthesized by our group are provided towards the end of the first chapter. The second chapter is dedicated to our efforts to synthesize new chiral NH-oxaziridines derived from camphor. The first part of this chapter describes the formation of 3-mono- and 3,3-disubstituted camphor nitrimine precursors. The synthesis of 3-alkyl-camphor nitrimines and their attempted conversion to oxaziridines are reported in section 2.2. Section 2.3 concerns the synthesis of 3-halo-camphor oxaziridines, and the section 2.4 attempts to synthesize 3,3-dihalo-camphor oxaziridines. Investigation of the process of ammonolysis of camphor nitrimine using ammonia is discussed in section 2.5. Section 2.6 is dedicated to the attempted formation of 3,3-diacetal camphor nitrimines.
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Daniel, Matthieu. "Nouvelles stratégies de synthèse d’hétérocycles polyazotés pour la conception de molécules énergétiques dérivées d’(aza)indazoles et de 1,3a,6a-triazapentalènes." Electronic Thesis or Diss., Orléans, 2019. http://www.theses.fr/2019ORLE3210.

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De par leurs vastes domaines d’applications, l’élaboration de nouvelles molécules énergétiques constitue une partie importante de la recherche en chimie organique. En outre, les hétérocycles azotés se positionnent comme d’excellents candidats du fait de leur densité et leur fort taux en azote qui garantissent à la fois une grande insensibilité et des propriétés énergétiques intéressantes. Ainsi, le développement de méthodes de synthèse innovantes est nécessaire et constitue un véritable défi. Dans ce contexte, nous nous sommes intéressés au long de cette thèse au développement de nouvelles méthodes de synthèse d’hétérocycles polyazotés et fonctionnalisés. Ainsi, l’étude d’une récente stratégie de synthèse d’(aza)indazoles nitrés, via une réaction tandem Staudinger/aza-Wittig, a pu être réalisée pour nous permettre d’accéder à de potentiels candidats énergétiques. Aussi, une méthode originale de synthèse de dérivés tricycliques de triazapentalène a été développée, à partir de substrats insensibles et facilement accessibles. La génération d’un azote électrophile, indispensable pour réaliser cette transformation, a été assurée par diverses amines hétéroaromatiques en présence d’iode hypervalent. Finalement, la valorisation de ces nouvelles méthodes pour accéder à des cibles pyrotechniques originales est présentée dans la dernière partie de cette thèse
Due to their wide range of applications, the elaboration of original energetic materials represents an important part of research in organic chemistry. Besides, the stability and the high explosive performances of azaheterocycles, provided by their compact and nitrogen rich structures, make them promising candidates for energetic applications. Thus, the development of innovative methodologies is essential and remains very challenging. In this context, we aimed at developing new methodologies to access functionalized nitrogen rich heterocycles. For this purpose, we first investigated a recent strategy giving access to polynitrated (aza)indazoles via a Staudinger/aza-Wittig tandem reaction. A second part was dedicated to the development of an original way to synthesize tricyclic triazapentalene derivatives from non-hazardous and readily available precursors. The generation of electrophilic nitrogen, essential to achieve this transformation, was ensured by various heteroaryl amines in presence of hypervalent iodine in mild conditions.The last part of this work focused on the application of these strategies to access new energetic materials
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Cino, Silvia <1985&gt. "Coupling Reactions Between Aromatic Carbon - and Nitrogen - Nucleophiles and Electrophiles: Reaction Intermediates, Products and their Properties." Doctoral thesis, Alma Mater Studiorum - Università di Bologna, 2016. http://amsdottorato.unibo.it/7566/1/TESI_DOTTORATO_CinoSilvia.pdf.

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During my PhD I was involved in many studies concerning the nucleophilic (SNAr) and electrophilic (SEAr) aromatic substitution reactions. My research activity was focused on the study of different electrophile/nucleophile combinations between strongly activated species, with the purpose to investigate on their reactivity, to detect new intermediates of the aromatic substitution reaction and to obtain new higly conjugated structures bearing contemporaneously electron donor and acceptor moieties on the same unit for application in different fields. Different reactions between both neutral or charged electrophilic and nucleophilic species were performed and from their combinations new products for applications in different fields (e.g. medicine, biology and materials) were obtained and new intermediates of the aromatic substitution reactions [e.g. Wheland (W), Meisenheimer (M), and even Wheland-Meisenheimer (WM)], were detected and characterized, mainly using NMR spectroscopic techniques. In particular the involved nucleophilic species were: tri- and diaminobenzene derivatives, trihydroxybenzene, trimethoxybenzene, anisole derivatives and aminothiazole derivatives; whereas the selected electrophilic species were: aryldiazonium ions, benzofuroxan and benzofurazan derivatives, thiophene derivatives and benzhydrylium ions. Furthermore, the last year of my PhD course, I spent a period in the Department of Chemistry, Ludwig-Maximilians-University of Munich, in collaboration with Prof. Herbert Mayr’s group, with the aim to investigate on the nucleophilic reactivities of di- and triaminobenzene derivatives performing their combination with different reference electrophiles, selected from the Mayr’s reactivity scales.
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Cino, Silvia <1985&gt. "Coupling Reactions Between Aromatic Carbon - and Nitrogen - Nucleophiles and Electrophiles: Reaction Intermediates, Products and their Properties." Doctoral thesis, Alma Mater Studiorum - Università di Bologna, 2016. http://amsdottorato.unibo.it/7566/.

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During my PhD I was involved in many studies concerning the nucleophilic (SNAr) and electrophilic (SEAr) aromatic substitution reactions. My research activity was focused on the study of different electrophile/nucleophile combinations between strongly activated species, with the purpose to investigate on their reactivity, to detect new intermediates of the aromatic substitution reaction and to obtain new higly conjugated structures bearing contemporaneously electron donor and acceptor moieties on the same unit for application in different fields. Different reactions between both neutral or charged electrophilic and nucleophilic species were performed and from their combinations new products for applications in different fields (e.g. medicine, biology and materials) were obtained and new intermediates of the aromatic substitution reactions [e.g. Wheland (W), Meisenheimer (M), and even Wheland-Meisenheimer (WM)], were detected and characterized, mainly using NMR spectroscopic techniques. In particular the involved nucleophilic species were: tri- and diaminobenzene derivatives, trihydroxybenzene, trimethoxybenzene, anisole derivatives and aminothiazole derivatives; whereas the selected electrophilic species were: aryldiazonium ions, benzofuroxan and benzofurazan derivatives, thiophene derivatives and benzhydrylium ions. Furthermore, the last year of my PhD course, I spent a period in the Department of Chemistry, Ludwig-Maximilians-University of Munich, in collaboration with Prof. Herbert Mayr’s group, with the aim to investigate on the nucleophilic reactivities of di- and triaminobenzene derivatives performing their combination with different reference electrophiles, selected from the Mayr’s reactivity scales.
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Eichman, Chad. "Development of Electrophilic Amination with Oximes for the Synthesis of Nitrogen-Containing Heterocycles; Transition Metal Catalysts for Carbon-Sulfur and Carbon-Carbon Bond Formation and Selective C-H Activation." The Ohio State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=osu1275430570.

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EL, ALAMI NAJAT. "Isolement et reactivite du derive zincique de (bromomethyl-2) acrylate d'ethyle : synthese de methylene-3 pyrrolidinone-3 potentiellement antineoplasique." Nantes, 1987. http://www.theses.fr/1987NANT2016.

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Reaction de l'organozinicique allylique prepare, avec divers electrophiles conduisant a des methylene-3 perhydrofurannones-2 et -pyrrolidones-2. Etude de l'activite de ces composes sur la leucamie p388
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Berkaoui, M'hamed. "Réactivité énaminique de β-aminothiophènes vis-à-vis de divers électrophiles. Accès à des hétérocycles thiophéniques azotés." Rouen, 1998. http://www.theses.fr/1998ROUES015.

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Le fort caractère énaminique des 3-aminothiophènes est responsable de la grande réactivité de la position 2 de l'hétérocycle vis-à-vis des réactifs électrophiles et des acides. L'action d'un aldéhyde en présence de sélénophénol, comme réducteur, et de traces acides, ouvre une voie d'accès aux 2-alkyl 3-aminothiophènes et à leurs dérivés acétamides et carbamates. Le mécanisme de cette réaction de C-alkylation suppose la formation d'un carbocation pseudo-benzylique intermédiaire mis en évidence par capture avec le thiophénol ou le pyrrole. En absence de réducteur, on observe une double alkylation aboutissant aux 2,2'-alkylidènebis(3-thiophénamines) et aux 2,2'-alkylidènebis(3-thiényl)acétamides et carbamates en partant de l'acétamide ou d'un carbamate correspondant. La formation de dithiénopyridines à partir des 2,2'-alkylidènebis(3-thiophènamines) illustre la seconde propriété de ces composés, qui découle de la C-protonation, et que nous appelons transamination acido-catalysée. Elle permet d'expliquer la formation de dithiéno[3,2-b:2',3'-e]pyridines. Nous proposons aussi un mécanisme faisant intervenir préalablement une étape d'oxydation. Lorsque l'aldéhyde utilisé est substitué en α , on observe la formation d'une double liaison plus rapide que la réaction du carbocation avec le substrat. Elle conduit aux composés α-vinyliques non fonctionnalisés. Par le même processus, les composés β-(3-amino 2-thiényl)vinylcétones, esters et nitriles sont obtenus à partir des acétals fonctionnalisés correspondants. Ce résultat permet d'établir le mécanisme de formation des thiéno[3,2-b]pyridines fonctionnalisées en position 6 à partir du 3-aminothiophène et de deux équivalents d'acétal fonctionnalisé. Nous accédons également, de manière efficace aux 2-allyl 3-aminothiophènes par α-allylation directe ou par réarrangement de dérivés N-allylés.
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Couture, Karine. "Etude de la métallation en série diazinique 1) premier échange iode-lithium avec les alkylamidures de lithium 2) amination électrophile 3) première métallation sans groupe directeur." Rouen, 1995. http://www.theses.fr/1995ROUES020.

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Ce travail consiste en l'étude de la réaction de métallation en série diazinique. Dans une première partie, nous avons pu mettre en évidence pour la première fois en série diazinique, un mécanisme d'halogen-dance avec migration de l'iode. De plus, nous avons pu observer pour la première fois dans cette série, un exceptionnel échange iode-métal avec les alkylamidures de lithium. Cette réaction a été appliquée à la synthèse de leshmaniacides. Dans une seconde partie, nous avons mis au point l'amination électrophile par métallation en série diazinique. Cette réaction d'amination a été appliquée à la synthèse de molécules biologiquement actives et nous a permis d'accéder à un azaanalogue de la Névirapine ainsi qu'à des précurseurs de sulfamides connus. Dans une troisième partie, nous avons tenté d'élargir la gamme des groupes ortho-directeurs en série pyrimidinique (NHCOtBu, CONHtBu). Dans la dernière partie, une nouvelle fonctionnalisation directe des diazines sans groupe ortho-directeur a été réalisée avec succès
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Debleds, François. "Complexation d'électrophiles aromatiques par des bases hétérocycliques ambidentes : structure et réactivité d'adduits carbones et azotes pyrroliques indoliques et imidazoliques." Paris 6, 1987. http://www.theses.fr/1987PA066330.

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Structure et formation des complexes de Meisenheimer du trinitro-1,3,5 benzène avec divers indoles, pyrroles, imidazoles ; étude cinétique de la décomposition de ces complexes. Etude cinétique de la protonation du kryptopyrrole en solution aqueuse.
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Jacquelin, Jean-Marie. "Fonctionnalisation par métallation d'amino et d'hydroxy quinoléines : applications à la synthèse de furo quinoléines." Rouen, 1987. http://www.theses.fr/1987ROUES033.

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L'amino-2 quinoléine est fonctionnalisée par métallation en position 3. Les amino-3 et -4 quinoléines ont également été métallées respectivement sur les sommets 2 et 8 mais n'ont pu être fonctionnalisées par des électrophiles carbonés. Les hydroxy-2, -3 et -4 quinoléines masquées sous forme de carbamates sont lithiés régiosélectivement sur les carbones 3, 4 et 3 respectivement. Les dérivés ortho substitués préparés par réaction d'aldéhydes sur les intermédiaires lithiés sont utilisés pour la synthèse de furo-quinoléines
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Book chapters on the topic "Electrophilic nitrogens"

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Beak, Peter, Timothy A. Johnson, Dwight D. Kim, and Sung H. Lim. "Enantioselective Synthesis by Lithiation Adjacent to Nitrogen and Electrophile Incorporation." In Organolithiums in Enantioselective Synthesis, 139–76. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_5.

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Beaulieu, Pierre l., and robert dáziel. "Addition of electrophilic organoselenium reagents to carbon-carbon double bonds." In Organoselenium Chemistry, 35–66. Oxford University PressOxford, 1999. http://dx.doi.org/10.1093/oso/9780198501411.003.0003.

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Abstract Since the discovery in the late 1950s that species of the type RSeX add stereospecifically to simple alkenes, electrophilic selenium-based reagents have provided the synthetic chemist with an ever-growing arsenal of methods for the construction of complex organic molecules. Comprehensive reviews of the rich chemistry characteristic of electrophilic selenium species have appeared. In this chapter we have concentrated on the practical aspects of this chemistry, limiting ourselves to the generation and use of novel organoselenium electrophiles. Representative examples are provided of applications to carbon-oxygen, carbon-nitrogen and carbon-carbon bond formation. A final section is devoted to the growing importance of homochiral electrophilic selenium reagents and their application to asymmetric synthesis.
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Xiong, T., and Y. Li. "1.2 Copper(I) Hydride Catalyzed Transformations." In Base-Metal Catalysis 1. Stuttgart: Georg Thieme Verlag KG, 2023. http://dx.doi.org/10.1055/sos-sd-238-00029.

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AbstractCopper(I) hydride is a binary metal hydride that, due to the relatively low electropositivity of copper, features a rather covalent metal−hydrogen bond. This readily obtained species can either be pre-prepared or generated in situ, and reacts with various unsaturated bonds or polar single bonds to form intermediates with reactive C—Cu bonds, which can be captured by various electrophiles to form new chemical bonds and new stereocenters. In this chapter, some representative examples in this domain are discussed, with the methods divided into four sections based on the different kinds of electrophiles. The first three sections cover asymmetric C—N, C—C, and C—B bond formation with various electrophilic nitrogen sources, carbon-based reagents, and boranes, and the last section focuses on some racemic transformations.
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Davies, David T. "Indoles." In Aromatic Heterocyclic Chemistry. Oxford University Press, 1992. http://dx.doi.org/10.1093/hesc/9780198556602.003.0007.

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This chapter focuses on indoles. Fusion of a benzene ring onto the C2/C3 positions of pyrrole formally produces the corresponding benzopyrrole known as indole. Indole is a ten π-electron aromatic system. As with pyrrole, delocalization of the lone pair of electrons from the nitrogen atom is necessary for aromaticity. A consequence of this delocalization is that the lone pair is not available for protonation under moderately acidic conditions. Pyrrole is therefore just like indole, another weakly basic heterocycle. Another similarity to pyrrole is that being an ‘electron-rich’ heterocycle indole easily undergoes aromatic electrophilic substitution, and is also rather unstable to oxidative conditions. However, an important difference emerges here, in that whereas pyrrole preferentially reacts with electrophiles at the C2/C5 positions, indole substitutes selectively at the C3 position. The chapter then looks at the synthesis, electrophilic substitution, and anion chemistry of indoles.
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Grimmett, M. R. "Electrophilic Displacement." In Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-012-00750.

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Hajos, G., and Z. Riedl. "Electrophilic Substitution." In Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-012-00854.

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Larsen, R. D., and D. Cai. "Electrophilic Acylation." In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-00816.

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lvarez, M., and J. A. Joule. "Electrophilic Acylation." In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-01287.

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lvarez, M., and J. A. Joule. "Electrophilic Substitution." In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-01296.

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lvarez, M., and J. A. Joule. "Electrophilic Alkylation." In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-01469.

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You might also be interested in the extended bibliographies on the topic 'Electrophilic nitrogens' for particular source types:
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