Academic literature on the topic 'Passerini Reaction'

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Journal articles on the topic "Passerini Reaction"

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Ichikawa, Yoshiyasu, Toshiki Yamasaki, Keisuke Nakanishi, Yutaro Udagawa, Seijiro Hosokawa, and Toshiya Masuda. "Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products." Synthesis 51, no. 11 (March 14, 2019): 2305–10. http://dx.doi.org/10.1055/s-0037-1610867.

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A pathway is proposed for the biosynthesis of the unique homodimeric terpene, halichonadin H. The proposed biosynthetic pathway involves two key Passerini reactions of eudesmane-type terpene isocyanides. The Passerini reaction of a model terpene isocyanide and formaldehyde afforded an α-hydroxy acetamide, which was further subjected to oxidation and a second Passerini reaction. This reaction sequence furnished an α-hydroxy malonamide connected with two identical terpene units which is the identical structural motif found in halichonadin H.
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Onwukamike, Kelechukwu Nnabuike, Stéphane Grelier, Etienne Grau, Henri Cramail, and Michael A. R. Meier. "On the direct use of CO2in multicomponent reactions: introducing the Passerini four component reaction." RSC Advances 8, no. 55 (2018): 31490–95. http://dx.doi.org/10.1039/c8ra07150k.

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We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO2.
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Boukis, Andreas C., Baptiste Monney, and Michael A. R. Meier. "Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions." Beilstein Journal of Organic Chemistry 13 (January 9, 2017): 54–62. http://dx.doi.org/10.3762/bjoc.13.7.

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The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone–α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli–Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.
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Zhao, Long, Mao-Lin Yang, Min Liu, and Ming-Wu Ding. "New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence." Beilstein Journal of Organic Chemistry 18 (March 4, 2022): 286–92. http://dx.doi.org/10.3762/bjoc.18.32.

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A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes 1, benzoic acid (2), and isocyanides 3 produced the azide intermediates 4, which were treated sequentially with triphenylphosphine, isocyanates (or CS2), and secondary amines to give polysubstituted 3,4-dihydroquinazolines 8 and 4H-3,1-benzothiazines 11 in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.
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Shaabani, Ahmad, Hassan Farhid, Mohammad Mahdi Rostami, and Behrouz Notash. "Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions." SynOpen 05, no. 03 (June 22, 2021): 167–72. http://dx.doi.org/10.1055/a-1533-3823.

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AbstractAn efficient and straightforward approach has been established for the preparation of a new class of depsipeptide structures via isocyanide-based consecutive Bargellini–Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were obtained via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via a Passerini multicomponent-reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes. The depsipeptides thus prepared have more flexible structures than their pseudopeptidic analogues.
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Neo, Ana G., and Carlos F. Marcos. "Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations." Proceedings 9, no. 1 (November 19, 2018): 6. http://dx.doi.org/10.3390/ecsoc-22-05864.

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In continuation of our recent research on the development of novel multicomponent reactions with isocyanides, we have used, for the first time, enols as the acid components in Ugi- and Passerini-type reactions. Thus, electron-poor pyrrolidinodiones react with aldehydes, amines, and isocyanides to give the enaminic four-component adducts. Conversely, in the absence of the amine component, careful control of the reaction conditions allows the involvement of one or two molecules of isocyanide to afford, selectively, either Passerini-type or pseudo-enol-Ugi-type products. These unprecedented condensations of isocyanides, aldehydes, amines, and 4-substituted pyrrolidine-2,3-diones constitute an excellent strategy for the preparation of new biologically relevant pyrrolidinones having peptidic or pseudo-peptidic groups on carbon 3.
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Haven, Joris J., Evelien Baeten, Jonathan Claes, Joke Vandenbergh, and Tanja Junkers. "High-throughput polymer screening in microreactors: boosting the Passerini three component reaction." Polymer Chemistry 8, no. 19 (2017): 2972–78. http://dx.doi.org/10.1039/c7py00360a.

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The Passerini three-component reaction (Passerini-3CR) has been studied via on-line microreactor/electrospray ionisation mass spectrometry (MRT/ESI-MS) reaction monitoring to demonstrate the high-throughput screening potential of microreactors for macromolecular design.
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Reza Kazemizadeh, Ali, and Ali Ramazani. "Synthetic Applications of Passerini Reaction." Current Organic Chemistry 16, no. 4 (February 1, 2012): 418–50. http://dx.doi.org/10.2174/138527212799499868.

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Giustiniano, Mariateresa, Lisa Moni, Gian Tron, Luca Sangaletti, Sveva Pelliccia, Andrea Basso, and Ettore Novellino. "Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island." Synthesis 50, no. 18 (August 15, 2018): 3549–70. http://dx.doi.org/10.1055/s-0037-1610193.

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The formation of the key short-lived intermediate nitrilium ion in the Passerini and Ugi reactions was recognized early in the discovery of these two-multicomponent transformations. Surprisingly, the idea of intramolecularly intercepting it, eluding the attack by the carboxylate, and thus interrupting the normal course of the reaction, was missed by chemists for several decades. In this review we describe, in an exhaustive manner, the reported synthetic approaches, which can be categorized as interrupted Passerini/Ugi reactions. Besides, the clear goal of this review is to show the potential of these transformations, whilst highlighting the underexplored combinations of reagents toward the identification of novel interrupted Passerini/Ugi reactions.1 Introduction2 The Interrupted Ugi Reaction2.1 The Interrupting Functional Group is Present on the Amine Reactant2.2 The Interrupting Functional Group is Present on the Isocyanide Reactant2.3 The Interrupting Functional Group is Present on the Carbonyl Reactant3 The Interrupted Passerini Reaction3.1 The Interrupting Functional Group is Present on the Carbonyl Reactant3.2 The Interrupting Functional Group is Present on the Isocyanide Reactant4 Conclusions and Future Outlook
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Andreana, Peter R., Chang C. Liu, and Stuart L. Schreiber. "Stereochemical Control of the Passerini Reaction." Organic Letters 6, no. 23 (November 2004): 4231–33. http://dx.doi.org/10.1021/ol0482893.

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Dissertations / Theses on the topic "Passerini Reaction"

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Ben, Abdessalem Abdelbari. "Réactions multicomposant à base des isonitriles." Thesis, Université Paris-Saclay (ComUE), 2016. http://www.theses.fr/2016SACLY024/document.

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Les réactions multicomposant à base d'isonitrile (I-MCR) combinées à des transformations de post-condensation constituent des outils de synthèse extrêmement puissants pour la préparation de structures moléculaires complexes et diverses avec de nouvelles propriétés pharmacologiques.Dans un premier temps, nous nous sommes intéressés à l'extension du couplage de Ugi-Smiles aux dérivés de purines, en utilisant la 6-mercaptopurine comme partenaire de couplage. Cette méthodologie permet un accès direct et rapide aux dérivés d'adénine avec des rendements modérés à bons à partir de précurseurs simples et facilement accessibles.Par la suite, nous avons démontré que les produits d'addition Ugi dérivés d'aldéhydes aromatiques peuvent être convertis en 2-pyrrolines par addition d'accepteurs de Michael, sous irradiation par micro-ondes. La réaction peut se dérouler via la formation inhabituelle d’ylures azométhines suivie d'une cycloaddition [3 + 2] avec des accepteurs de Michael.Enfin, nous avons montré que les adduits Passerini issus de cinnamaldéhyde peuvent être efficacement convertis en α-cétoamides lorsqu'ils sont traités en milieu basique et dans des conditions de chauffage sous irradiations micro-ondes
The isocyanide based multicomponent reactions (I-MCRs) with subsequent post-condensation transformations constitute extremely powerful synthetic tools for the preparation of structurally diverse complex molecules with novel properties.In this context, we first investigated the extension of Ugi-Smiles coupling to purines, by using 6-mercaptopurine as coupling partner. This methodology allows direct access to adenine derivatives in moderate to good yields starting from readily available precursors.Then, we demonstrated that Ugi adducts derived from aromatic aldehydes may be converted to pyrrolines via addition of Michael acceptors under microwave irradiation. The reaction may proceed via unusual formation of azomethine ylides followed by a [3+2] cycloaddition using Michael acceptors.Finally, we described that the Passerini adducts of cinnamaldehyde and analogues may be efficiently converted into α-ketoamides when heated with a base under microwave conditions
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Ben, Abdessalem Abdelbari. "Réactions multicomposant à base des isonitriles." Electronic Thesis or Diss., Université Paris-Saclay (ComUE), 2016. http://www.theses.fr/2016SACLY024.

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Les réactions multicomposant à base d'isonitrile (I-MCR) combinées à des transformations de post-condensation constituent des outils de synthèse extrêmement puissants pour la préparation de structures moléculaires complexes et diverses avec de nouvelles propriétés pharmacologiques.Dans un premier temps, nous nous sommes intéressés à l'extension du couplage de Ugi-Smiles aux dérivés de purines, en utilisant la 6-mercaptopurine comme partenaire de couplage. Cette méthodologie permet un accès direct et rapide aux dérivés d'adénine avec des rendements modérés à bons à partir de précurseurs simples et facilement accessibles.Par la suite, nous avons démontré que les produits d'addition Ugi dérivés d'aldéhydes aromatiques peuvent être convertis en 2-pyrrolines par addition d'accepteurs de Michael, sous irradiation par micro-ondes. La réaction peut se dérouler via la formation inhabituelle d’ylures azométhines suivie d'une cycloaddition [3 + 2] avec des accepteurs de Michael.Enfin, nous avons montré que les adduits Passerini issus de cinnamaldéhyde peuvent être efficacement convertis en α-cétoamides lorsqu'ils sont traités en milieu basique et dans des conditions de chauffage sous irradiations micro-ondes
The isocyanide based multicomponent reactions (I-MCRs) with subsequent post-condensation transformations constitute extremely powerful synthetic tools for the preparation of structurally diverse complex molecules with novel properties.In this context, we first investigated the extension of Ugi-Smiles coupling to purines, by using 6-mercaptopurine as coupling partner. This methodology allows direct access to adenine derivatives in moderate to good yields starting from readily available precursors.Then, we demonstrated that Ugi adducts derived from aromatic aldehydes may be converted to pyrrolines via addition of Michael acceptors under microwave irradiation. The reaction may proceed via unusual formation of azomethine ylides followed by a [3+2] cycloaddition using Michael acceptors.Finally, we described that the Passerini adducts of cinnamaldehyde and analogues may be efficiently converted into α-ketoamides when heated with a base under microwave conditions
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Oelmann, Stefan [Verfasser], and M. A. R. [Akademischer Betreuer] Meier. "Unimolecular Micelles and their Application Possibilities via the Passerini Three-Component Reaction / Stefan Oelmann ; Betreuer: M. A. R. Meier." Karlsruhe : KIT-Bibliothek, 2018. http://d-nb.info/1164081004/34.

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Elmamouni, Elhachemia. "Nouvelles applications de la réaction de Passerini dans des réactions de type Friedel-Crafts et Tsuji-Trost." Thesis, Université Paris-Saclay (ComUE), 2017. http://www.theses.fr/2017SACLX011/document.

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L’élaboration de synthèses rapides et efficaces de molécules complexes à partir de substrats de départ simples en utilisant un minimum d’étapes constitue un véritable enjeu de la chimie organique contemporaine. Dans ce contexte, les réactions multicomposant, grâce à leur capacité à créer plusieurs liaisons en une étape, offrent une grande efficacité pour synthétiser des structures d’une grande complexité moléculaire. Par ailleurs, la catalyse organométallique s’est considérablement développée ces dernières années, pour devenir un outil de choix pour la formation de liaisons carbone-carbone. La réaction de Tsuji-Trost est notamment un des plus connues dans ce domaineDans le cadre de cette thèse, la découverte de post-condensations originales à partir d’adduits obtenus par les réactions multicomposant impliquant un isonitrile est l’axe majeur de nos recherches. Ces réactions permettent un accès efficace à un large éventail de composés hétérocycliques.Tout d’abord, nous avons développé une nouvelle voie efficace de synthèse des indolylacétamides via une cascade Passerini/Friedel-Crafts à partir d’adduits de Passerini et d’indoles en présence d’un acide de Lewis. Une version monotope de cette cascade a été ainsi développée.Par ailleurs, nous avons exploité la réactivité des hydrazones N-monosubstitués en tant que bis-nucléophile 1,3 en vue de préparer divers dérivés de 2-pyrazolines via une cascade Tsuji-Trost/Cyclisation pallado-catalysée à partir des adduits de Passerini ou de phosphonates. Dans le but de préparer des 2-pyrazolines énantiosélectivement enrichis, une version énantiosélective de cette cascade a été également réalisée à partir d’adduits de Passerini.Enfin, la mise au point d’une nouvelle cascade Tsuji-Trost/Cyclisation exploitant l’allyle méthyle carbonate a permis l’accès rapide à des motifs hétérocycliques de type oxazolidine-2,4-diones en exploitant le dioxyde de carbone généré in situ
The development of rapid and efficient syntheses of complex molecules from simple starting substrates using a minimum of steps is a real challenge of contemporary organic chemistry. In this context, multicomponent reactions, thanks to their ability to create several one-step bonds, offer a high efficiency in synthesizing structures of great molecular complexity. Moreover, organometallic catalysis has developed considerably in recent years, becoming a tool of choice for the formation of carbon-carbon bonds. The Tsuji-Trost reaction is specially well known in this field.In this thesis, the discovery of the original post-condensations from the adducts obtained by multicomponent reactions involving isonitrile is the major axis of our research. These reactions allow efficient access to a wide range of heterocyclic compounds.First, we have developed a new efficient pathway for the synthesis of indolylacetamides via the Passerini/Friedel-Crafts cascade from the Passerini adducts and indole in the presence of a Lewis acid. A one-pot version of this cascade has been also developed.Furthermore, we have exploited the reactivity of N-monosubstituted hydrazones as 1,3-bis-nucleophile in order to prepare various 2-pyrazoline derivatives via a pallado-catalyzed Tsuji-Trost/Cyclisation cascade from the Passerini adducts or Phosphonates. In order to prepare enantioselectively enriched 2-pyrazolines, the enantioselective version of this cascade was also realized from the Passerini adduct.Finally, the development of a new Tsuji-Trost/Cyclization cascade from the Passerini adducts and the allyl methyl carbonate provide straight fast and efficient access to oxazolidine-2,4-diones heterocyclic units by exploiting the carbon dioxide generated in situ
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Bos, Maxence. "Synthèse de [gamma]-lactones polyfonctionnelles chirales par catalyse énantiosélective." Thesis, Reims, 2015. http://www.theses.fr/2015REIMS017.

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La mise au point de méthodologies de synthèse permettant d’obtenir des substances énantiopures présentant une diversité structurale importante est une préoccupation majeure de la chimie contemporaine. L’efficacité de ces approches doit être désormais évaluée au regard de critères tel que la pureté optique et l’analyse de l’impact écologique des processus mis en jeu. Au cours de ce travail nous avons développé de nouvelles méthodologies permettant d’accéder à des γ-lactones polyfonctionnelles chirales. La 5-hydroxyfuran-2(5H)-one, petite molécule bio-sourcée, a servi d’élément clé pour la construction du cycle γ-lactone. Dans une première approche, des γ-lactones chirales possédant une grande diversité structurale ont été obtenues par une séquence réactionnelle « one pot ». Une première étape de catalyse organique a permis d’activer le transfert énantiosélectif d’acides boroniques sur la 5-hydroxyfuran-2(5H)-one ; l’adduit chiral obtenu a ensuite été engagé dans une réaction de Passerini pour construire le cycle lactone. Dans une deuxième partie, nous avons mis au point des réactions d’alkylation de γ-lactones, catalytiques et énantiosélectives, pour la formation de γ-lactones possédant un centre quaternaire. L’utilisation de complexes du palladium et de l’iridium a permis d’effectuer des réactions d’Alkylation Allylique Asymétrique avec un très bon contrôle de l’induction asymétrique. Le squelette carboné des lactones obtenues par AAA a permis d’effectuer une fonctionnalisation inédite d’hétérocycles aromatiques par des réactions sigmatropiques [3,3]. Enfin des réactions d’alkylations énantiosélectives induites par un catalyseur organique ont été évaluées
The development of new synthetic pathway leading to enantiopure compounds with significant structural diversity is an ongoing challenge in many fields of chemistry. The efficiency of these processes has to be evaluated, not only in term of quantitative criteria, such as yields and/or optical purities of obtained compounds, but also by analyzing the environmental impact of the different processes involved. In this work, we sought to develop new methodologies for the synthesis of polyfunctional chiral γ-lactones. The 5-hydroxyfuran-2(5H)-one, a bio-based molecule, was used as a platform to the construction of the γ-lactone ring. In the first part of our work, a variety of chiral γ-lactone displaying a great structural diversity were obtained by a one-pot sequential reaction. First, a step of enantioselective organocatalysis allowed the activation for the transfer of boronic acids on the hydroxyfuran-2(5H)-one; then the chiral adduct formed was engaged in a Passerini reaction leading to the construction of the lactone ring. In a second part, our efforts focused then on the development of catalytic asymmetric alkylation reactions leading to the construction of γ-lactones bearing an all-carbon quaternary stereocenter. Asymmetric allylic reactions were carried out with a very good control of the selectivity of the reaction by the use of palladium and iridium complexes catalysts. Theses lactones bearing an [1,5]-diene scaffold were then engaged in a sigmatropic [3,3] reaction opening a path for a new approach to the functionalization of aromatic heterocycles. Finally, the use of organic enantioselective catalysis was envisioned for the creation of all-quaternary stereocenters
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Martinand-Lurin, Élodie. "Hétérocycles et réactions pallado-catalysées : développements méthodologiques, études mécanistiques et application en synthèse totale." Thesis, Paris 11, 2015. http://www.theses.fr/2015PA112018/document.

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Le développement de nouvelles méthodologies de synthèse toujours plus efficaces, sélectives et éco-compatibles apparaît comme un défi permanent tant l’intérêt suscité pour les composés hétérocycliques est important. Ce projet de thèse s’articule autour de plusieurs axes dans ce domaine.Tout d’abord, nous avons exploité la réactivité des N-(sulfonyl) et N-(sulfamoyl)aziridines en tant que précurseurs de dipôles 1,3 en vue de préparer divers 1-azaspiro[5.n]alcanes. L’étude mécanistique de cette réaction de cycloaddition [3+2] réalisée par calculs DFT permet de montrer que l’étape cinétiquement déterminante de la réaction est la formation du dipôle 1,3 ; la force motrice étant la fermeture du cycle à cinq chaînons.Nous nous sommes également attachés à valoriser le savoir-faire du laboratoire dans le domaine des transferts catalytiques de nitrènes (aziridination et amination C-H) dans le cadre du projet de synthèse totale de la pactamycine, aminocyclopentitol hautement fonctionnalisé.Par ailleurs, la mise au point d’une cascade Passerini-Smiles/Réduction/Cyclisation et d’une séquence monotope Passerini-Double-Smiles/SNAr permet un accès rapide et efficace à des motifs hétérocycliques de type 1,4-benzoxazin-3-ones. Conduisant à des familles régioisomères de produits, ces deux voies de synthèse se sont avérées complémentaires.Parallèlement, une nouvelle méthodologie basée sur l’ouverture pallado-catalysée de thiocyclopropanes a permis d’obtenir de nouveaux hétérocycles de type thiochromènes. Compte tenu des nombreuses fonctionnalisations envisageables, ces composés semblent très prometteurs dans le domaine de la chimie hétérocyclique.Enfin, des études électrochimiques et RMN couplées à des calculs DFT ont été entreprises afin d’élucider le mécanisme mis en jeu lors des couplages pallado-catalysés entre un halogénure d’aryle, un isonitrile et un nucléophile
The development of new and more efficient synthetic methodologies, selective and eco-friendly seems to be an ongoing challenge as the interest in the heterocyclic compounds is important. All the studies performed during the last three years are divided in several axes in this field.First, the reactivity of N-(sulfonyl) and N-(sulfamoyl) aziridines as precursors of 1,3-zwitterionic species was explorated in order to obtain various 1-azaspiro[5.n]alkanes. The mechanism of the reaction has been studied by DFT calculations. The initial formation of the zwitterionic 1,3-dipole has been found to be the rate-determining step whereas the five-membered ring closure appeared to be the driving force.We tried to apply our expertise in the field of catalytic nitrene transfers (aziridination and C-H amination) to the total synthesis of pactamycin, highly functionalized aminocyclopentitol compound.Furthermore, the developments of a Passerini-Smiles/reduction/cyclization cascade and of a one-pot Passerini-Double-Smiles/SNAr sequence provide straightforward and efficient accesses to 1,4-benzoxazin-3-ones. These paths are complementary as they lead to regioisomers.Meanwhile, a new methodology based on Pd-catalyzed thiocyclopropanes ring opening gave thiochromenes. Due to their high synthetic potential, these compounds appear to be very promising scaffolds in heterocyclic chemistry.Finally, electrochemical and NMR studies coupled with DFT calculations have been done in order to elucidate the mechanism involved in the Pd-catalyzed couplings between an aryl halide, an isocyanide and a nucleophile
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Benchekroun, Mohamed. "Synthèse multicomposants et évaluation pharmacologique de nouveaux adduits de Ugi et de Passerini pour le traitement de la maladie d'Alzheimer." Thesis, Besançon, 2014. http://www.theses.fr/2014BESA3007/document.

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La maladie d'Alzheimer est la pathologie neurodégénérative la plus courante affectant les personnes âgées. Cette neuropathologie se caractérise par une étiologie complexe dont le déficit en acétylcholine, les plaques amyloïdes, les dégénérescences neurofibrillaires ou le stress oxydant en sont les principaux acteurs.Au cours de cette thèse, nous nous sommes intéressés à l'application des réactions multicomposants de Ugi et de Passerini, pour la synthèse de nouveaux adduits multi-cibles basées sur différents motifs antioxydants et anticholinestérasiques. Ces réactions permettent d'accéder à une vaste diversité chimique en une étape, ce qui les rend adaptées pour la synthèse rapide de molécules ayant plusieurs pharmacophores d'intérêt et ciblant ainsi différentes cause étiologiques de la maladie d'Alzheimer.Au total, 56 composés finaux, répartis dans cinq séries, ont été synthétisés :les alpha-acylaminocarboxamides prototypes (série A)les hybrides tacrine-acide férulique (série B)les hétérotrimères tacrine-mélatonine-acides antioxydant (série C)> les hybrides donépézil-acide férulique (série D)^ les dérivés chromone (série E)Toutes les séries ont été évaluées pour leur capacité à inhiber les enzymes cholinestérases et leur pouvoir antioxydant. L'hépatotoxicité des séries B et C. portant un motif tacrine, a été évaluée sur les cellules HepG2. Par ailleurs, l'étude de la série B a été complétée par d'autres tests pharmacologiques, physico-chimiques et toxicologiques.Ces différents travaux démontrent et valident l'utilisation des réactions de Ugi et de Passerini dans le développement de molécules multi-cibles pour le traitement potentiel de la maladie d'Alzheimer
Alzheimer's disease (AD) is thé most common type of dementia affecting elderly people. This neuropathology is characterized by a highiy complex and intricated etiology including cholinergic déficit, amyloid deposits, neurofibrillary tangles and oxidative stress.During this thesis, we sought to apply Ugi and Passerini multicomponent reactions for thé synthesis of new multi-target adducts based on différent antioxidant and anticholinergic scaffolds.Thèse réactions provides access to a broad range of chemical diversity in a one-pot fashion, which makes them suitable for thé expeditious synthesis of molécules having several pharmacophores of interest and hitting différent targets related to thé multifaceted etiology of Alzheimer's disease.A total of 56 final compounds, spread over 5 séries, hâve been synthesized:alpha-acylaminocarboxamides prototypes (A séries)tacrine-ferulic acid hybrids (B séries)tacrine-melatonin-antioxydant acids heterotrimers (C séries)donepezil-ferulic acid hybrids (D séries)Chromone derivatives (E séries)Ail thé séries were tested for their ability to inhibit thé cholinesterases enzymes and for their antioxidant power. Hepatotoxicity of thé B and C séries, bearing a tacrine fragment, was evaluated on HepG2 cells. Moreover, thé study of thé B séries was supplemented by further pharmacological, physicochemical and toxicological tests (NMR conformational study, neuroprotection on SH-SY5Y cells. self-induced Abetai.42 peptide aggregation inhibition, docking ADMET).Such work demonstrated and validated thé use of Ugi and Passerini reactions for thé development of new multi-target directed molécules for thé potential treatment of AD
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陳彥男. "Synthesis of SARS-CoV Main Protease Inhibitors by Using Passerini Reaction as Key Step." Thesis, 2006. http://ndltd.ncl.edu.tw/handle/21997418423825933802.

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碩士
國立彰化師範大學
化學系
94
The Severe Acute Respiratory Syndrome is abbreviated as SARS, precededded in the colony caused of form virus by SARS and infected with the case in A.D. 2003, death rate is up to ten percent. SARS-CoV Mpro has been shown to be essential for replication and is thus a target for drug discovery. In this thesis the Passerini reaction was used to synthesize the core structures of anti SARS-CoV Mpro inhibitors . After activity screening, the compounds 48、49 and 50 showed potent inhibitions against SARS-CoV Mpro with IC50 1.5 μΜ、0.1 μΜ and 10 μΜ, respectively. Although these compounds are not the inhibitors we expected,the approach by using Passerini reaction as key step is a good way to form tripeptide libraries.
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Liu, Pin-Yi, and 劉品毅. "Synthesis of Boron-containing peptide Analogs(I);Synthesis of Multiple Boron-containing Analogs via Passerini Reaction(II)." Thesis, 2015. http://ndltd.ncl.edu.tw/handle/20373650734082653961.

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Abstract:
碩士
淡江大學
化學學系碩士班
103
Synthesis of Boron-containing peptide Analogs(I): In this research, we have designd and synthesized two series of boron-containing analogues. These compounds could be easily synthesized and purified via simple synthetic operations.More analogs are being synthesized and the result will be reported in due course. Synthesis of Multiple Boron-containing Analogs via Passerini Reaction(II): In this report, a Passerini three-component reaction with a boron- containing starting material in water under microwave irradiation was developed.We developed these compounds suitable for BNCT drugs.
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Chen, Hsien-Chi, and 陳賢祺. "Synthesis of Peptidyl Isocyano Boronate Ester using Boron-containing Aldehydes (I)Synthesis of Peptidyl Boron-containing Tetrazole Analogs (II)Synthesis of Boron-containing Analogs using Sequential Ugi 4CR/Passerini-3CR Reactions (III)." Thesis, 2016. http://ndltd.ncl.edu.tw/handle/34180779097997779514.

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Abstract:
碩士
淡江大學
化學學系碩士班
104
1. Synthesis of Peptidyl Isocyano Boronate Ester using Boron-containing Aldehydes : Isocyanide (or isonitrile) is a unique class of functional groups that appears in many biological active natural products. Many of these isocyanide-based natural products can be used as antitumor agents or antibiotics. Thus, incorporation of this functional group could potentially generate a biological interesting compound. In the first part of my research, I have successfully synthesized 2 boron-containing formamides by microwave assisted Ugi-3CR in good yields (92%-97%). At the same time, I have successfully converted these 2 boron-containing formamides to the corresponding boron-containing isocyanides. 2. Synthesis of Peptidyl Boron-containing Tetrazole Analogs : Tetrazole derivatives are often recognized for their impressive biological activities. The tetrazole ring is considered as a bioisostere of carboxylic acid, which possess a much-improved metabolic stability. In the second part of my research, I have successfully synthesized 2 boron-containing tetrazoles by microwave. 3. Synthesis of Boron-containing Analogs using Sequential Ugi 4CR/Passerini-3CR Reactions : Depsipeptide is a class of functional groups that frequently appears in variety of natural products. It composes of one ester group with at least one peptide bond(s). Therefore, inclusion of this functional group to the boron-containing compounds might generate interesting biologically active compounds. In the third part of my research, I have utilized Ugi-3CR to synthesize boron-containing formamides via microwave irradiation. These formamides were subjected to dehydration process where the corresponding isocyanides were obtained. The desired boron-containing isocyanides were then utilized as one of the building blocks in the Passerini-3CR to generate boron-containing depsipeptide analogs.
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Book chapters on the topic "Passerini Reaction"

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Li, Jie Jack. "Passerini reaction." In Name Reactions, 298. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_222.

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Li, Jie Jack. "Passerini reaction." In Name Reactions, 458–59. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_204.

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Li, Jie Jack. "Passerini reaction." In Name Reactions, 269. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_211.

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Li, Jie Jack. "Passerini reaction." In Name Reactions, 415–16. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_191.

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Li, Jie Jack. "Passerini Reaction." In Name Reactions, 424–26. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_115.

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Wang, Qian, Jieping Zhu, and Mei-Xiang Wang. "Enantioselective Passerini Reaction." In Asymmetric Synthesis II, 95–101. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527652235.ch13.

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Zhang, Jian, Xin-Xing Deng, Fu-Sheng Du, and Zi-Chen Li. "Sequence-Regulated Polymers via Combination of Orthogonal Passerini Three-Component Reaction and Thiol-ene Reaction." In ACS Symposium Series, 223–34. Washington, DC: American Chemical Society, 2014. http://dx.doi.org/10.1021/bk-2014-1170.ch015.

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Pirali, Tracey, Ubaldina Galli, Marta Serafini, Alessia Griglio, Armando A. Genazzani, and Gian Cesare Tron. "Drug Discovery for Soft Drugs on TRPV1 and TRPM8 Channels Using the Passerini Reaction." In Methods in Molecular Biology, 207–21. New York, NY: Springer New York, 2019. http://dx.doi.org/10.1007/978-1-4939-9446-5_13.

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Marqués-López, Eugenia, and Raquel P. Herrera. "Passerini Multicomponent Reactions." In Multicomponent Reactions, 283–305. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118863992.ch8.

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Kaïm, Laurent El, and Laurence Grimaud. "Ugi-Smiles and Passerini-Smiles Couplings." In Multicomponent Reactions in Organic Synthesis, 73–108. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527678174.ch04.

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Conference papers on the topic "Passerini Reaction"

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Rosalba, Thaíssa Pasquali F., Angélica de Fátima S. Barreto, and Carlos Kleber Z. Andrade. "Unexpected cleavage of an ester group by hydrogenolysis reactions of Passerini subtrates." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0351-1.

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Jakas, Andreja, Aleksandar Višnjevac, and Ivanka Jeric. "Peptides going sweet: Synthesis of glycopeptide hybrid structures using Passerini and Ugi reactions." In 35th European Peptide Symposium. Prompt Scientific Publishing, 2018. http://dx.doi.org/10.17952/35eps.2018.102.

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Barreto, Angélica de Fátima S., Otilie E. Vercillo, Ludger A. Wessjohann, and Carlos Kleber Z. Andrade. "Synthesis of Cyclic Pentadepsipeptoids Analogues of Sansalvamide A by Combination of Ugi and Passerini Reactions." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0298-2.

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