Relevant bibliographies by topics / Nitrone cycloaddition

Academic literature on the topic 'Nitrone cycloaddition'

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Published: 4 June 2021
Last updated: 8 February 2022

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Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers

Journal articles on the topic "Nitrone cycloaddition":

1

Charmier, Marie-Odile Januário, Najat Moussalli, Josette Chanet-Ray, and Sithan Chou. "1,3-Dipolar Cycloaddition Reactions of Nitrones with Unsaturated Methylsulfones and Substituted Crotonic Esters." Journal of Chemical Research 23, no. 9 (September 1999): 566–67. http://dx.doi.org/10.1177/174751989902300924.

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The cycloaddition reaction of nitrones to unsaturated methylsulfones and substituted crotonic esters gives a sole product or a mixture of tri- or tetra-substituted isoxazolidines, such that with disubstituted dipolarophiles the regiochemistry is dependent upon the nitrone and the vicinal electron-withdrawing group (CN or CO2Me) but with trisubstituted olefins, regiospecific cycloadditions are observed.
2

Strmiskova, Miroslava, Didier A. Bilodeau, Mariya Chigrinova, and John Paul Pezacki. "Phenanthridine-based nitrones as substrates for strain-promoted alkyne-nitrone cycloadditions." Canadian Journal of Chemistry 97, no. 1 (January 2019): 1–6. http://dx.doi.org/10.1139/cjc-2018-0253.

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Over the past decade, bioorthogonal chemistry that facilitates the efficient conjugation of biomolecules has expanded from the copper-catalyzed alkyne-azide cycloadditions to a multitude of diverse reactions, varying additives and reactional partners, and most often offering better alternatives with faster rates and lower toxicity of employed reactants. Among these, the copper-free strain-promoted cycloaddition reactions have been demonstrated to be more promising, offering a reaction without toxic metal catalysts and with faster inherent kinetic rate constants. The strain-promoted alkyne-nitrone cycloadditions are easily tunable from both the (strained) alkyne and nitrone perspective, both compounds giving the opportunity to modulate the rate of reaction by substituting various positions. Previously, acyclic nitrones have been evaluated in the strain-promoted alkyne-nitrone reactions; however, they were notably prone to hydrolysis. Some five-membered ring endocyclic nitrones developed concomitantly offered the advantage of relatively fast kinetics and better resistance to degradation in aqueous conditions and have been successfully used for labelling of biomolecules in living systems. Herein, we have prepared and studied nitrones inspired by the phenanthridine scaffold that efficiently undergo strain-promoted alkyne-nitrone reactions. Phenanthridine nitrones react fast with strained cyclooctynes with large bimolecular rate constants while maintaining bioorthogonality and resistance to hydrolysis.
3

Jäger, Volker, Wolfgang Frey, Yaser Bathich, Sunitha Shiva, Mohammad Ibrahim, Marco Henneböhle, Pierre-Yves LeRoy, and Mukhtar Imerhasan. "2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 821–32. http://dx.doi.org/10.1515/znb-2010-0708.

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2-Isoxazolines represent a well known class of heterocycles, readily accessible in particular by 1,3-dipolar cycloaddition of nitrile oxides to alkenes. 2-Isoxazolines are easily transformed into 2- isoxazolinium salts by N-methylation, and further into 3-isoxazolines by deprotonation. In contrast to the parent system, less is known concerning the chemistry of the derived classes, and potential applications in synthesis. - 2-Isoxazolinium salts, due to their iminium part, are prone to the attack of nucleophiles, and examples for this, addition of hydride (reduction) and C-nucleophiles like methylmagnesium bromide, cyanide, methane nitronate, and malonate are given. With these adducts, syntheses of β - and α-amino acids with OH-containing side chains have been effected. The cyanide products also are useful as precursors of branched, unsymmetrical 1,2-diamino polyols. - On the other hand, 3-isoxazolines due to their oxy-enamine part, represent species with nucleophilic sites and therefore react with electrophilic reagents. Examples given are [3+2] cycloadditions with nitrile oxides, [2+2] cycloadditions with dimethyl acetylenedicarboxylate, and [2+1] cycloaddition in the form of epoxidation which, however, led to a dihydro-1,3-oxazine nitrone by initial attack at the nitrogen atom, in an unprecedented oxidation/N-dealkylation/rearrangement sequence.
4

Parhi, Ajit K., and Richard W. Franck. "A Weinreb Nitrile Oxide and Nitrone for Cycloaddition." Organic Letters 6, no. 18 (September 2004): 3063–65. http://dx.doi.org/10.1021/ol0489752.

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Perzanowski, Herman P., Said S. Al-Jaroudi, Mohamed I. M. Wazeer, and Sk Asrof Ali. "Cyclic nitrone-ethene cycloaddition reactions." Tetrahedron 53, no. 34 (August 1997): 11869–80. http://dx.doi.org/10.1016/s0040-4020(97)00760-6.

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6

Toder, Bruce H., George B. Mullen, and Vassil St. Georgiev. "A Novel Nitrone Cycloaddition/Rearrangement." Helvetica Chimica Acta 73, no. 1 (January 31, 1990): 169–73. http://dx.doi.org/10.1002/hlca.19900730119.

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7

Black, DS, PA Keller, and N. Kumar. "Nitrones and Oxaziridines. XLVI. Formation of Pyrrolo[3,2,1-ij]Quinolines by Intramolecular Nitrone Cycloaddition." Australian Journal of Chemistry 46, no. 6 (1993): 843. http://dx.doi.org/10.1071/ch9930843.

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Intramolecular 1,3-dipolar cycloaddition occurs between nitrones derived from indole-7-carbaldehydes and adjacent allylic substituents on the indole nitrogen atoms. The resulting pyrroloquinoline derivatives (4a-i) have been characterized fully. A range of other potential precursors to cycloaddition reactions have been synthesized, but cyclization sequences have not been completed.
8

Grygorenko, Oleksandr O., Viktoriia S. Moskvina, Oleksandr V. Hryshchuk, and Andriy V. Tymtsunik. "Cycloadditions of Alkenylboronic Derivatives." Synthesis 52, no. 19 (June 24, 2020): 2761–80. http://dx.doi.org/10.1055/s-0040-1707159.

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook
9

Paśniczek, Konrad, Dariusz Socha, Margarita Jurczak, Jolanta Solecka, and Marek Chmielewski. "Synthesis of 8-homocastanospermine." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 534–39. http://dx.doi.org/10.1139/v06-032.

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The 1,3-dipolar cycloaddition of a five-membered cyclic nitrone derived from malic acid (4) and unsaturated D-threo-hexaldonolactone (1) leads to a single adduct 6, which can be transformed into the 8-homocastanospermine (13) via a sequence involving rearrangement of the six-membered lactone ring into the five-membered one, removal of the terminal carbon atom from the sugar chain, cleavage of the N—O bond, and the intramolecular alkylation of the nitrogen atom. The iminosugar (13) does not show any interesting inhibitory activity towards α- and β-glucosidases.Key words: iminosugars, homocastanospermine, nitrones, aldono-1,5-lactone, 1,3-dipolar cycloaddition, glucosidases.
10

Jones, Raymond C. F., Jason N. Martin, and Paul Smith. "Chiral nitrone reagents for cycloaddition reactions." Journal of Heterocyclic Chemistry 37, no. 3 (May 2000): 481–86. http://dx.doi.org/10.1002/jhet.5570370306.

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You might also be interested in the extended bibliographies on the topic 'Nitrone cycloaddition' for particular source types:
Journal articles Dissertations / Theses

Dissertations / Theses on the topic "Nitrone cycloaddition":

1

Henderson, A. J. "Studies towards solid-phase nitrone cycloaddition reactions." Thesis, University of Cambridge, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.603957.

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The work outlined in this thesis is directed towards the use of resin-bound nitrones in 1,3-dipolar cycloaddition reactions towards the synthesis of heterocyclic compounds. Chapter one provides a brief introduction of a solid-phase synthesis, highlighting some key elements within the technique. A detailed review of solid-phase 1,3-dipolar cycloaddition reactions follows this. Chapter two describes the solution-phase model studies carried out towards an intramolecular 1,3-dipolar cycloaddition on a solid support. Interesting developments such as the effect of the nitrone substituent R on the cycloaddition of 2.121 and various enolate alkylation methods are reported. Furthermore, studies towards novel linker methodologies based on sulfur linked substrates such as 2.57 are outlined. Fig. 11,050A. In Chapter 3, the conventional intramolecular 1,3-dipolar cycloaddition methodology is translated to the solid-phase with limited success. Preparation of the isoxazolidine 3.8 is reported, with subsequent cleavage. Additionally, the problems encountered with alkylation reactions and resin stability are extensively discussed. Fig. 11,050B. Chapter 4 introduces intramolecular nitrone-olefin 1,3-dipolar cycloaddition reactions in solution and solid-phase. The conventionally synthesised adduct 4.21 is compared with the solid-phase synthesised analogue 4.40 with some interesting differences in the stereochemical outcome of both.
2

Williams, Simon Frederick. "The intramolecular nitrone cycloaddition route to alkaloids." Thesis, University of Cambridge, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.328912.

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3

Alkayar, Ziad Tariq Ibrahim. "Synthesis of iboga alkaloids using cascade cyclisation, nitrone cycloaddition." Thesis, University of Sheffield, 2017. http://etheses.whiterose.ac.uk/16898/.

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4

Erhard, Thomas. "Totalsynthese von (±)-Codein durch 1,3-dipolare Cycloaddition." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2011. http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-69013.

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Die Nitron-Cycloaddition an ein dearomatisiertes Phenol ermöglichte den leichten Aufbau des Phenanthrengerüstes von Codein in der gewünschten Konfiguration. Weitere Schritte führten mit kompletter Diastereoselektivität zu Allopseudocodein und nach Allylverschiebung durch Hydrolyse der Chlorcodide schließlich zu (±)-Codein.
5

Lopes, Tiago Luiz. "Modificação do produto natural (-)-∝- Bisabolol." Universidade de São Paulo, 2010. http://www.teses.usp.br/teses/disponiveis/97/97136/tde-22082013-112422/.

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O (-)-?-bisabolol é um produto natural abundante no Brasil. É extraído de várias espécies de plantas. Possui atividades biológicas reconhecidas, que o torna extremamente interessante para as indústrias de cosméticos e fármacos. O trabalho de pesquisa tem como objetivo principal sua modificação buscando, com isso, melhorar as atividades biológicas ou agregar novas potencialidades biológicas. Durante estas transformações procura-se, principalmente, empregar metodologias ecologicamente corretas (Green Chemistry). O trabalho foi dividido em 3 (três) partes principais: Aminoredução, oxidação e cicloadição. A primeira parte consiste na preparação da imina (N-benzilfenilmetanoamina) e transformação, da mesma, em uma amina secundária, através de aminação redutiva. Na segunda, oxidação das aminas secundárias e do bisabolol e, na terceira, estudo das reações de cicloadições. As oxidações das aminas secundárias (dibenzilamina e 1,2,3,4-tetraidroisoquinolina) forneceram as nitronas correspondentes (N-óxido de N-benzilidenobenzilamina e N-óxido de 3,4-diidroisoquinolina). A oxidação (epoxidação) do Bisabolol forneceu uma mistura de óxidos de Bisabolol: Óxido de Bisabolol - B: 1-metil-1-[5-(4-metil-3-cicloexenil)tetraidro-2-furanil]etil álcool e Óxido de Bisabolol - A: (3S)-2,2,6-trimetil-6-(4-metil-3-cicloexenil)tetraidro-2H-3-piranol. A oxidação alílica do Bisabolol, forneceu o tetraidro-2,2,6-trimetil-6-(4-metil-3-cicloexen-1-il)-4H-piran-4-ona. A cicloadição [1+2] entre diclorocarbeno e o bisabolol originou o 4-(2,2-dicloro-3,3-dimetilciclopropil)-2-(7,7-dicloro-6-metilbiciclo [4.1.0]hept-3-il)-2-butanol. A reação de cicloadição [2+3] entre a nitrona (N-óxido de 3,4-diidroisoquinolina) e o dipolarófilo (butil vinil éter) forneceu a isoxazolidina 1,5,6,10b-tetraidro-2H-isoxazolol[3,2-a]isoquinolina-2-il butil éter.
The (-)-?-bisabolol is a natural product available in a large quantity in Brazil. It is extracted of several specimens of trees and has recognized biological activity that made it a so interesting product for cosmetic and pharmaceutic industries. The research has as mean goal the modification of (-)-?-bisabolol a natural product. The modification has intended, improve the biological activity or create new biological activity. The methods applied always consider condition to protect the environment (Green Chemistry). The research has three main parts: amino reduction, oxidation and cycloaddition. The first part based on the reaction to synthesize the imines (N-benzylphenilmethanoamine) and with the amine reduction synthesis the secondary amine. A second part was oxidizing the secondary amines and bisabolol. The third part is a research about cycloaddition. The amines oxidation (dibenzylamine e 1,2,3,4-tetrahydroisoquinoline) gave the nitrones [N-benzylidenebenzylamine N-oxide and 3,4-dihydroisoquinoline N-oxide] respectively. The Bisabolol oxidation (epoxidation reaction) gave a mix of bisabolol oxide: The Bisabolol oxide B, 1-methyl-1-[5-(4-methyl-3-ciclohexenyl)tetrahydro-2-furanyl]ethyl alcohol and The Bisabolol oxide A, (3S)-2,2,6-trimethyl-6-(4-methyil-3-ciclohexenyl) tetrahydro-2H-3-piranol. The alilic oxidation from Bisabolol also was achieved and gave the tetrahydro-2,2,6-trimethyl-6-(4-methyl-3-cyclohexen-1-yl)-4H-pyran-4-one. The cycload-dition [1+2] between diclorocarbene and bisabolol gave, 4-(2,2-dicloro-3,3-dimethylciclopropil)-2-(7,7-dicloro-6-methylbiciclo[4.1.0]hept-3-yl)-2-butanol. The cycloaddition [2+3] with nitrones (3,4-dihydroisoquinoline N-oxide) and dipolarophile (butyl vinyl ether) gave the isoxazolidine 1,5,6,10b-tetrahydro-2H-isoxazolol[3,2-a]isoquinoline-2-yl butyl ether.
6

Nguyen, Thanh Binh. "Nouveaux Développements Méthodologiques pour la Cycloaddition 1,3-Dipolaire de Nitrones." Phd thesis, Université du Maine, 2008. http://tel.archives-ouvertes.fr/tel-00382503.

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Lors de ces travaux de thèse, nous nous sommes intéressés à de nouveaux développements méthodologiques en cycloaddition 1,3-dipolaire de nitrones suivant deux axes principaux :
• l'étude de la réactivité des N-alcényloxazolidin-2-ones en tant que nouveaux dipolarophiles aza-substitués en cycloaddition 1,3-dipolaire à demande inverse vis-à-vis de nitrones.
• la mise en jeu de nitrones aspartiques originales en cycloaddition vis-à-vis de différents alcènes pour fournir des précurseurs d'aspartates α-substitués par une chaîne fonctionnelle.
Dans un premier temps, nous avons mis au point deux méthodes inspirées de celles de la littérature en partant d'une oxazolidin-2-ones pour synthétiser les N-alcényloxazolidin-2-ones: (i) vinylation cupro-catalysée utilisant un bromure d'alcényle, (ii) condensation avec un aldéhyde. Ces méthodes simples, générales, directes et à hauts rendements nous ont permis d'accéder aux N-alcényloxazolidin-2-ones de structure diverse.
Ces N-alcényloxazolidin-2-ones ont montré une grande réactivité en tant que dipolarophile vis-à-vis de diverses nitrones dans différentes conditions : thermiques (avec/sans solvant) et promues par TMSOTf. Les 5-aza-isoxazolidines diversement substituées originales ont été obtenues avec des rendements élevés mais de faibles stéréosélectivités. Cette limitation − due à l'instabilité configurationnelle des nitrones activées et à la flexibilité conformationnelle des N-alcényloxazolidin-2-ones − a été résolue par utilisation de la nitrone chirale à géométrie fixe de Tamura : les adduits trans-β sont obtenus avec d'excellents sélectivités
La tranformation des adduits issus de la N-benzyl-α-carbonyloxyéthylnitrone en dérivés aspartates carboxy-différenciés a été ensuite étudiée par une séquence en deux étapes (i) ouverture du cycle isoxazolidinique en aspartimide via N-quaternarisation par benzylation (ii) attaque chimiosélective d'un hétéronucléophile sur la fonction amide. Les aspartates carboxy-différenciés ont été obtenus avec de bons rendements, des excès énantiomériques élevés en version non-racémique, et un grand degré de diversité fontionnelle en ω (ester, amide, acide).
L'étude a été étendu à la cycloaddition 1,3-dipolaire des N-vinyloxazolidin-2-ones β,β-difluorées originales avec la N-benzyl-α-carbonyloxyéthylnitrone : les 4,4-difluoro-5-aza-isoxazolidines sont obtenues avec de bons rendements malgré une faible stéréosélectivité probablement due à un mécanisme non-concerté.
Notre étude a été complétée par l'accès à des dérivés d'α-aminoacides α,α-disubstitués via cycloaddition 1,3-dipolaire mettant en jeu de nouvelles nitrones aspartiques d'une stablilité configurationnelle inédite. Ce type de nitrones − préparé facilement par addition d'une N-benzylhydroxylamine sur un acétylènedicarboxylate – a montré une grande réactivité vis-à-vis d'une large gamme d'alcènes de différents natures électroniques. Les adduits issus des éthers vinyliques ont été obtenus avec de hauts sélectivités trans. L'extension asymétrique utilisant soit un éther vinylique chiral , soit une nitrone chirale a été effectuée et a permis l'obtention facile des adduits diastéréomériquement enrichis. A partie de ces adduits, un premier accès réussi aux dérivés aminoacides α,α-disubstitués a été réalisé en trois étapes. La diversification de cette méthodologie a été effectuée en utilisant une nitrone aspartique carboxy-différenciée.
7

Chigrinova, Mariya. "Development of New Bioorthogonal Strain-Promoted Alkyne-Nitrone Cycloaddition Methodology for Applications in Living Systems." Thesis, Université d'Ottawa / University of Ottawa, 2014. http://hdl.handle.net/10393/31281.

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Nitrones are alternatives to azides in rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes. To evaluate the differences between nitrones and azides we have performed kinetic studies of strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions of biarylazacyclooctynone (BARAC) with various acyclic and cyclic nitrones. The reactions were conducted under pseudo first-order reaction conditions using UV-visible spectroscopy. The reactivity of the acyclic nitrones was evaluated by varying the stereoelectronic and steric character of substituents at both the α-aryl and nitrogen positions. Cyclic nitrone reactivity was assessed according to the size of the ring and additional steric and strain effects. The obtained second-order rate constants for reactions of BARAC with cyclic nitrones were found to be greater than those for acyclic nitrones. However, all nitrones employed in the kinetic studies herein displayed significantly greater reactivity than azides in the analogous cycloadditions with BARAC. It is of particular note that the five-membered cyclic nitrones showed exceptional reactivity and, if used as rapid alternatives to azides in reactions with BARAC, can increase the reaction rates by up to 50 fold. An attempt to synthesize an allylated BARAC analogue is also described; the rearrangement reaction leading to the unexpected products is reported. The reaction rate for the novel rearrangement under both neutral and acidic conditions was obtained and plausible mechanisms for formation of products are proposed. Based on the results reported herein we anticipate that development of a labelling probe based on BARAC and a five-membered cyclic nitrone would allow for significant decrease of the concentrations of labelling reagents, thereby minimizing reaction time and reagent usage in life sciences applications. Nevertheless, a possible labelling decrease due to side reactions should be given consideration for prolonged labelling.
8

Oukani, El Hassan. "Synthèse de sucres à longue chaîne par réaction de cycloaddition 1,3 dipolaire." Nancy 1, 1995. http://www.theses.fr/1995NAN10065.

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De nouvelles voies de synthèse de sucres à longue chaîne qui constituent le squelette de base de produits biologiquement importants ont été explorées. En effet, la synthèse d'un sucre à 11 atomes de carbone qui constitue la partie active de l'hikizimycine, utilisant la cycloaddition 1,3 dipolaire, a été étudié. Nous avons montré que le couplage d'une nitrone chirale dérivée de l'acide L-tartrique et d'une oléfine acyclique chirale dérivée du D-mannose permettrait la préparation de cet undécose. D’autres substrats ont été étudiés et nous avons montré que la nitrone dérivée de l'acide D-tartrique avait un comportement tout à fait diffèrent. Dans ce cas, la cycloaddition, au lieu de fournir deux isomères comme précédemment, donne quatre isomères montrant l'importance de la configuration du centre asymétrique en alpha de la fonction nitrone. Dans le même contexte, nous avons montré que le motif pyruvique peut être introduit avec succès en position anomère d'un glucide. Ainsi, le couplage d'une nitrone chirale dérivée du D-arabinose avec différentes oléfines captodatives permet la synthèse des cycloadduits attendus qui peuvent être des précurseurs d'agents thérapeutiques. Enfin, une approche permettant l'introduction de longues chaînes latérales souhaitées sur des aldehydopyranosides protégés a été explorée. Nous avons montré que la condensation d'organomagnésiens sur ces sucres est une réaction diastéréoselective permettant la synthèse des précurseurs de lipopolysaccharides bactériens
9

Wang, Lianjie. "New biobased chemicals from HMF and GMF : Applications of Morita-Baylis-Hillman reaction and nitrone 1,3-dipolar cycloaddition." Thesis, Lyon, 2020. http://www.theses.fr/2020LYSEI026.

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Ces dernières années, la conception de nouveaux produits de chimie fine à partir de biomasse et de molécules plateformes est devenue un domaine de recherche très actif. Le 5-hydroxyméthylfurfural (HMF) s’est révélé une des briques les plus prometteuses parmi les dérivés des hydrates de carbone, en raison de la richesse de sa chimie liée à son haut niveau de fonctionalisation. Son analogue glucosylé, bien que moins disponible, le glucosyloxyméthylfurfural (GMF), est également un aldéhyde biosourcé furanique intéressant et capable d’être transformé en une multitude de produits chimiques nouveaux conservant un motif glucidique complet. Cette thèse est une contribution à l’utilisation de ces deux briques moléculaires dans la conception de nouveaux produits destinés à la chimie fine, par le biais de deux réactions, la réaction de Morita-Baylis-Hillman (MBH) et la cycloaddition de nitrones. L’application de cette stratégie dans la conception de nouveaux tensioactifs a aussi été étudiée. Premièrement, nous avons étudié le cas de la réaction de MBH du HMF et GMF avec les cycloalcenones dans l’eau pure. De nouvelles stuctures hautement fonctionnalisées ont pu être ainsi obtenues pour la première fois dans des conditions douces et sures, et dans un fort niveau d’économie d’atomes. Deuxièmement, nous avons étudié la possibilité de conduire la réaction de MBH du HMF et du GMF avec des acrylates et autres alcènes déficients en électrons en absence totale de solvant. Les réactions de cycloaddition 1,3-dipolaire des nitrones du HMF et du GMF offrent de nouvelles voies synthétiques vers les isoxazolidines biosourcées. La séquence de reactions « formation de la nitrone-cycloadditiopn dipolaire » peut être effectuée soit dans une approche à plusieurs composants (réaction multicomposants), soit en deux étapes successives. Dans une dernière partie, nous avons étudié la possibilité d’utiliser ces deux routes pour la conception de nouveaux tensioactifs dans le cadre d’une collaboration avec la Prof Véronique RATAJ et le Dr Fermin ONTIVEROS de l’équipe CISCO de l’unité de recherche UCCS à Lille. Les résultats préliminaires de l’évaluation physicochimique ont montré un réel intérêt de ces composés dont les propriétés sont facilement ajustables par des modifications structurales simples et qui obtenus par une séquence directe et originale
The design of new fine chemicals from biomass and platform molecules has recently become a very active field of research. 5-Hydroxymethylfurfural (HMF) is considered as one of the most promising renewable building blocks derived from carbohydrates, due to the rich chemistry offered by its high level of functionality. Its glucosylated analogue glucosyloxymethylfurfural (GMF), though much less available, is also an interesting biobased furanic aldehyde able to provide a range of novel architectures which include a remaining full carbohydrate moiety. The present thesis is a contribution to the use of these two building blocks for the design of novel fine chemicals, using notably two reactions, namely the Morita-Baylis-Hillman reaction, and the cycloaddition of nitrones. The application of these strategies for designing novel surfactants was also investigated. First, we investigated the MBH reaction of HMF and GMF with cycloalkenones using pure water as solvent. New functionalized scaffolds have been prepared in mild and safe conditions with remarkable atom-economy by this route for the first time. Then we investigated the possibility to run MBH reactions of HMF and GMF with acrylates or other alkenes in absence of any solvent. The 1,3-dipolar cycloaddition reactions of nitrones obtained from HMF and GMF offer novel synthetic routes towards biobased isoxazolidines. The sequence “nitrone formation-cycloaddition reaction” can be performed either in a multicomponent approach or in a stepwise one. In the last part, we addressed the possibility to use these two routes for the design of novels biobased surfactants, in the frame of a collaboration with Prof Véronique RATAJ and Dr Fermin ONTIVEROS of the CISCO team of the UCCS research unit in Lille. Preliminary results on their surfactants properties have been obtained, and indicate a real interest of these compounds which exhibit easily adjustable properties based on simple structural variations, and which are obtained in an easy straightforward and original synthetic sequence
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Ben, Ayed Achich Kawther. "Synthèse énantiosélective d'aminoacides disubstitués polyfonctionnels via cycloaddition dipolaire d'α-carboxy cétonitrones." Thesis, Le Mans, 2016. http://www.theses.fr/2016LEMA1013/document.

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Abstract:
Lors de ces travaux de thèse, nous nous sommes intéressés au développement de deux voies différentes de cycloaddition dipolaire-1,3 (CD-1,3) asymétrique pour accéder à des acides aminés disubstitués polyfonctionnels nouveaux de façon stéréochimiquement contrôlée.Dans la première partie, nous avons réalisé l’étude de la cycloaddition dipolaire-1,3 diastéréosélective entre différentes nitrones fonctionnelles et différents éthers vinyliques chiraux. La CD-1,3 de la cétonitrone aspartique et de l’éther vinylique du (R) ou (S) stéricol s'opère avec un double contrôle diastéréochimique élevé. Ce contrôle est possible en raison de la stabilité de la nitrone sous une forme (E) qui favorise l’approche exo, facialement contrôlée par le dipolarophile. La N-déprotection chimiosélective de l'adduit fournit une isoxazolidine sous une forme diastéréo- et énantiomériquement pure qui peut être transformée en dérivé d’acide aminé après N-acylation et coupure de la liaison N-O selon un processus dismutatif.Dans la deuxième partie, nous avons réalisé une étude approfondie de la cycloaddition dipolaire-1,3 organocatalysée entre différentes cétonitrones dérivées d’acides aminés vis-à-vis de dipolarophiles pauvres en électrons de type énal ou ynal. Avec le (E)-crotonalldéhyde, de hautes diastéréo- et énantiosélectivités sont obtenues en présence du catalyseur de MacMillan. Cette réaction organocatalysée a été étendue à une variété de d'α-carboxy cétonitrones différemment substituées, ainsi qu'à différents énals β-substitués par un groupement alkyle moyennant une modification de la nature du co-acide. En revanche, les ynals ne montrent aucune réactivité vis à vis des cétonitrones en conditions organocatalytiques. Notre étude a été complétée par l’accès des dérivés d’amino-acides polyhydroxylés par ouverture des adduits obtenus par la voie énantiosélective en utilisant les énals comme dipolarophiles. Cette étude préliminaire permet d’envisager d’accéder à des analogues de la myriocine
During this thesis, we were interested to develop two different ways of 1,3 dipolar cycloaddition to reach enantiopure disubstituted polyfunctionnal amino acids.We have described in a first part the diastereoselective 1,3-dipolar cycloaddition between an aspartic nitrone and chiral vinyl ethers. The aspartic ketonitrone and vinyl ether of (R) or (S) stericol led to high diastreocontrols. This control is due to the stability of the nitrone under (E) geometry which favors the exo approach, facially controlled by the dipolarophile. The chemoselective N-deprotection of this adduct leads to a diastereo- and enantiomerically pure isoxazolidine which affords the target DAA after N-acylation and N-O ring opening by a dismutative pathway. In a second part, we describe the synthesis of isoxazolidines obtained by organocatalytic enantioselective 1,3-dipolar cycloaddition between an alanine-derived nitrone and an enal or an ynal as the dipolarophile. With enals β-substituted by alkyl groups, good diastereoselectivities and ees were obtained in the presence of the MacMillan catalyst. These organocatalyzed conditions can be applied to a range of carboxy ketonitrones, and to different enals, provided an appropriate choice of the co-acid. Ynals show no reactivity under these organocatalytic conditions, although they lead regioselectively to polyfunctional quaternary isoxazolines under thermal conditions.Our study was achieved by the access of polyhydroxylated amino acids derived from opening adducts obtained by the enantioselective route using enals as dipolarophiles. This study allows to envisage the enantioselective synthesis of analogs of myriocin
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Books on the topic "Nitrone cycloaddition":

1

Lucarelli, Michael A. Cycloadditions with organosulfur and organonitrogen addends and the cleavage of carbon-sulfur and carbon-nitrogen bonds. 1986.

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Book chapters on the topic "Nitrone cycloaddition":

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Yang, Xin, Pan Xu, and Ying Xue. "Mechanism and regioselectivity of the cycloaddition between nitrone and dirhodium vinylcarbene catalyzed by Rh2(O2CH)4: a computational study." In Highlights in Theoretical Chemistry, 49–57. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-662-47845-5_7.

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Jones, Raymond C. F. "Nitrones." In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 1–81. New York, USA: John Wiley & Sons, Inc., 2003. http://dx.doi.org/10.1002/0471221902.ch1.

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Sharp, John T. "Nitrile Ylides and Nitrile Imines." In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 473–537. New York, USA: John Wiley & Sons, Inc., 2003. http://dx.doi.org/10.1002/0471221902.ch7.

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Jäger, Volker, and Pedro A. Colinas. "Nitrile Oxides." In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 361–472. New York, USA: John Wiley & Sons, Inc., 2003. http://dx.doi.org/10.1002/0471221902.ch6.

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Mandal, Bablee, and Basudeb Basu. "Synthesis of β-Lactams Through Alkyne–Nitrone Cycloadditions." In Topics in Heterocyclic Chemistry, 85–110. Berlin, Heidelberg: Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/7081_2012_85.

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Tamura, Osamu. "Geometry-Controlled Cycloaddition ofC-Alkoxycarbonyl Nitrones: Synthetic Studies on Nonproteinogenic Amino Acids." In Methods and Applications of Cycloaddition Reactions in Organic Syntheses, 151–74. Hoboken, New Jersey: John Wiley & Sons, Inc., 2014. http://dx.doi.org/10.1002/9781118778173.ch06.

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Fišera, L., U. A. R. Al-Timari, and P. Ertl. "Stereoselectivity of 1,3-Dipolar Cycloaddition of Glycosyl Nitrones toN-Arylmaleimides." In ACS Symposium Series, 158–71. Washington, DC: American Chemical Society, 1992. http://dx.doi.org/10.1021/bk-1992-0494.ch011.

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De Sarlo, Francesco, and Fabrizio Machetti. "Condensation of Primary Nitro Compounds to Isoxazole Derivatives: Stoichiometric To Catalytic." In Methods and Applications of Cycloaddition Reactions in Organic Syntheses, 205–22. Hoboken, New Jersey: John Wiley & Sons, Inc., 2014. http://dx.doi.org/10.1002/9781118778173.ch08.

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Pellegrini-Moïse, Nadia, and Mylène Richard. "Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes." In Topics in Heterocyclic Chemistry, 27–49. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2019_28.

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Suga, Hiroyuki, and Kennosuke Itoh. "Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Imines, Nitrile Oxides, Diazoalkanes, and Carbonyl Ylides." In Methods and Applications of Cycloaddition Reactions in Organic Syntheses, 175–204. Hoboken, New Jersey: John Wiley & Sons, Inc., 2014. http://dx.doi.org/10.1002/9781118778173.ch07.

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Conference papers on the topic "Nitrone cycloaddition":

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Reddy, Annapureddy Rajasekar, Zhen Guo, Fung-Ming Siu, Chun-Nam Lok, Fuli Liu, Kai-Chung Yeung, Cong-Ying Zhou*, and Chi-Ming Che. "Highly Selective Tandem Nitrone Formation/1,3-Dipolar Cycloaddition Catalyzed by Ruthenium Porphyrin." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_20138270315.

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Bastrakov, Maxim, Alexey Starosotnikov, Alexey Fedorenko, and Vladislav Nikol’skyа. "REACTIONS OF NITROPYRIDINES WITH NUCLEOPHILES: SUBSTITUTION, ADDITION, CYCLOADDITION." In Chemistry of nitro compounds and related nitrogen-oxygen systems. LLC MAKS Press, 2019. http://dx.doi.org/10.29003/m744.aks-2019/168-170.

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Komarova, Ol’ga, Ruslan Baichurin, and Nataliya Aboskalova. "GEMINALLY ACTIVATED 4-PHENYL-1-NITRO-1,3-BUTADIENES IN CYCLOADDITION REACTIONS." In Chemistry of nitro compounds and related nitrogen-oxygen systems. LLC MAKS Press, 2019. http://dx.doi.org/10.29003/m791.aks-2019/352-355.

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Momo, Patrícia B., Ricardo B. Ayres, Timothy J. Brocksom, and Kleber T. de Oliveira. "1,3-Dipolar Cycloaddition Reactions of meso-Tetra(2’- thienyl)porphyrins with a Nitrile Oxide." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201391291318.

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Ramasami, Ponnadurai, John Joule, Luis Domingo, Sabina Jhaumeer-Laulloo, and Lydia Rhyman. "1,3-Dipolar Cycloaddition of Nitrile Oxides to [C60]fullerene: A Density Functional Theory Study." In The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00655.

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Freeman, Colin, Aisling Ni Cheallaigh, Ishwar Singh, and Frances Heaney. "Isoxazole linked oligonucleotide conjugates by on resin and previously clicked nitrile oxide alkyne cycloadditions." In XVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2011. http://dx.doi.org/10.1135/css201112333.

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7

Merino, P., T. Tejero, S. Anoro, and F. Merchan. "1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones to Vinyl Ethers and a,b-Unsatureted Esters." In The 3rd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1999. http://dx.doi.org/10.3390/ecsoc-3-01718.

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