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Littérature scientifique sur le sujet « Indole N-alkylation »

Auteur : Grafiati
Publié le 14 mars 2023

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Articles de revues sur le sujet "Indole N-alkylation"

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Yi, Zi-Juan, Jian-Ting Sun, Tian-Yu Yang, Xian-Yong Yu, Xiao-Li Han et Bang-Guo Wei. « Cu(OTf)2-catalyzed C3 aza-Friedel–Crafts alkylation of indoles with N,O-acetals ». Organic & ; Biomolecular Chemistry 20, no 11 (2022) : 2261–70. http://dx.doi.org/10.1039/d1ob02383g.

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An efficient approach to access functionalized indole derivatives has been developed through Cu(OTf)2-catalyzed C3 aza-Friedel–Crafts alkylation of substituted indoles 5a–5m, N-methyl-pyrrole with linear N,O-acetals 4a–4l.
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Trubitsõn, Dmitri, et Tõnis Kanger. « Enantioselective Catalytic Synthesis of N-alkylated Indoles ». Symmetry 12, no 7 (17 juillet 2020) : 1184. http://dx.doi.org/10.3390/sym12071184.

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During the past two decades, the interest in new methodologies for the synthesis of chiral N-functionalized indoles has grown rapidly. The review illustrates efficient applications of organocatalytic and organometallic strategies for the construction of chiral α-N-branched indoles. Both the direct functionalization of the indole core and indirect methods based on asymmetric N-alkylation of indolines, isatins and 4,7-dihydroindoles are discussed.
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Gardette, Daniel, Jean-Claude Gramain, Marie-Eve Lepage et Yves Troin. « Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons ». Canadian Journal of Chemistry 67, no 2 (1 février 1989) : 213–19. http://dx.doi.org/10.1139/v89-036.

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The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety. This reaction was studied in order to achieve the synthesis of indole alkaloid synthons. Trials of regioselectivity control were made by using groups with enhanced steric hindrance. The reactivity of secondary enaminones was tested, and the ratio of C-alkylation to N-alkylation was shown to be dependent on the nature of the aromatic substituent. During this work, new hexahydrocarbazolones were synthesized, with substituents on the A ring or the modified C ring. Keywords: photocyclization, aryl enaminones, indole alkaloids, hexahydrocarbazolones-4, cyclopenta[b]indoles.
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Qiu, Zhongxuan, Rui Sun, Kun Yang et Dawei Teng. « Spiro Indane-Based Phosphine-Oxazolines as Highly Efficient P,N Ligands for Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles and Allylic Etherification ». Molecules 24, no 8 (21 avril 2019) : 1575. http://dx.doi.org/10.3390/molecules24081575.

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A series of indane-based phosphine-oxazoline ligands with a spirocarbon stereogenic center were examined for palladium-catalyzed asymmetric allylic alkylation of indoles. Under optimized conditions, high yields (up to 98%) and enantioselectivities (up to 98% ee) were obtained with a broad scope of indole derivatives. The ligand was determined to be the most efficient P,N-ligand for this reaction. Moreover, the ligand was also efficient for Pd-catalyzed asymmetric allylic etherification with hard aliphatic alcohols as nucleophiles.
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Wang, Chengyuan, Zhuopeng Li, Jiong Zhang et Xin-Ping Hui. « Asymmetric N-alkylation of indoles with isatins catalyzed by N-heterocyclic carbene : efficient synthesis of functionalized cyclic N,O-aminal indole derivatives ». Organic Chemistry Frontiers 7, no 13 (2020) : 1647–52. http://dx.doi.org/10.1039/d0qo00237b.

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Kumar, Nivesh, Arindam Maity, Vipin R. Gavit et Alakesh Bisai. « A catalytic N-deacylative alkylation approach to hexahydropyrrolo[2,3-b]indole alkaloids ». Chemical Communications 54, no 65 (2018) : 9083–86. http://dx.doi.org/10.1039/c8cc04117b.

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An efficient synthetic strategy to diversely functionalized hexahydropyrrolo[2,3-b]indole alkaloids is described featuring a key Pd(0)-catalyzed deacylative alkylation of N-acyl 3-substituted indoles. The reaction can be performed only using 1 mol% of Pd(PPh3)4 in the presence of 1.2 equivalent of both triethylborane and KOtBu.
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Ding, Zhenhua, et Naohiko Yoshikai. « C2-Alkylation of N-pyrimidylindole with vinylsilane via cobalt-catalyzed C–H bond activation ». Beilstein Journal of Organic Chemistry 8 (14 septembre 2012) : 1536–42. http://dx.doi.org/10.3762/bjoc.8.174.

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Direct C2-alkylation of an indole bearing a readily removable N-pyrimidyl group with a vinylsilane was achieved by using a cobalt catalyst generated in situ from CoBr2, bathocuproine, and cyclohexylmagnesium bromide. The reaction allows coupling between a series of N-pyrimidylindoles and vinylsilanes at a mild reaction temperature of 60 °C, affording the corresponding alkylated indoles in moderate to good yields.
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Trubitsõn, Dmitri, Jevgenija Martõnova, Kristin Erkman, Andrus Metsala, Jaan Saame, Kristjan Kõster, Ivar Järving, Ivo Leito et Tõnis Kanger. « Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis ». Synthesis 52, no 07 (26 novembre 2019) : 1047–59. http://dx.doi.org/10.1055/s-0039-1690751.

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An asymmetric phase-transfer-catalyzed N-alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.
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Huang, Bing-Bing, Liang Wu, Ren-Rong Liu, Ling-Ling Xing, Ren-Xiao Liang et Yi-Xia Jia. « Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters ». Organic Chemistry Frontiers 5, no 6 (2018) : 929–32. http://dx.doi.org/10.1039/c7qo01014a.

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Enantioselective Friedel–Crafts C2-alkylations of 3-substituted indoles with trifluoropyruvates and cyclic α-ketiminoesters were developed, delivering indole-containing α-hydroxyesters and α-aminoesters in excellent enantioselectivities.
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Mérour, J. Y., et F. Cossais. « Regioselective N-Alkylation of Methyl Indole-2-carboxylate ». Synthetic Communications 23, no 13 (juillet 1993) : 1813–20. http://dx.doi.org/10.1080/00397919308011281.

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Thèses sur le sujet "Indole N-alkylation"

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Balestri, Lorenzo Jacopo Ilic. « SYNTHESIS OF ANTIFUNGAL COMPOUNDS ». Doctoral thesis, Università di Siena, 2022. http://hdl.handle.net/11365/1203145.

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Systemic fungal infections represent a threat to public health, and annually more than 150 million people suffer from fungal diseases. This worrisome data reflects the growing group of patients with immunocompromised conditions: due to cancer chemotherapy, organ transplanting or affected by AIDS, and the outbreaks of azoles resistant strains. Moreover, the global emergency caused by SARS-CoV-2 led to long term hospitalizations, and intubation increased the susceptibility to developing fungal infections. Therefore, now more than ever, the challenge of developing new antifungal drugs is dramatically urgent. Our research group has been interested in the great potential of guanylated compounds as new antifungal agents since 2007. During these 15 years, three series of derivatives, characterized by an amidinoureas scaffold, have been developed. The structure of these compounds is new and not shared with other antifungal drugs present on the market. Consequently, they show remarkably antifungal activity, especially among Candida strains resistant to azole drugs. The first chapter of my thesis deals with synthesizing new antifungal compounds with a macrocyclic amidinourea scaffold. Firstly, a novel compound, BM37, was synthesized through a convergent approach using the ring-closing metathesis (RCM)as a key step. Secondly, we decided to conduct advanced biological investigations of our lead compound, BM1. Consequently, we face the need to prepare this compound on a gram scale. To achieve this result, we changed the synthetic route and took inspiration from Fukuyama’s work designing a new strategy to obtain 1 gram of BM1. The second chapter of my thesis explores the design and synthesis of novel inhibitors targeting human chitinases. This project started when we investigated a putative target for the amidinoureas compounds endowed with antifungal activity. This research led us to the Chitinase family. In particular, our interest fell on human chitinases due to their involvement in chronic inflammatory lung diseases. The development of new human chitinase inhibitors, characterized by two different chemical scaffolds, is the aim of this second chapter. The former was the macrocyclic amidinoureas scaffold. Here three derivatives: BM56, BM57 and BM58, were synthesized and evaluated on human chitinases. The latter explored the chemical space related to the 6-piperazine-1-ylpyrazine-2-carboxamide, a new scaffold that emerged from a structure-based virtual screening. In this case, we synthesized a small, focused library of derivatives. The third chapter of my thesis describes my work as visiting PhD student at Uppsala University. During this period, I have been involved in the alkylation of the N position of 3-methyl indole with several cyclic ketones using a green and efficient amide coupling reagent, the TP3®. Finally, the last chapter contains chemical and biological data of all the compounds presented in the thesis.
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Charvieux, Aubin. « Autotransfert d’hydrogène catalysé par du nickel hétérogène pour la formation de liaisons C-C et C-N ». Thesis, Lyon, 2019. http://www.theses.fr/2019LYSE1139.

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La méthodologie d’autotransfert d’hydrogène permet d’alkyler une large gamme de nucléophiles en utilisant des alcools comme agents alkylants. De manière avantageuse, le seul sous-produit de ces réactions à haute économie d’atome est l’eau. Dans ce contexte, un catalyseur de nickel sur silice-alumine (65 m% Ni/SiO2-Al2O3) a été utilisé pour former des liaisons C-C, notamment par α-alkylation de cétones avec des alcools, dont le méthanol. La caractérisation complète de ce catalyseur a été effectuée, y compris après utilisation. Ni/SiO2-Al2O3 s’est révélé recyclable sur 5 essais pour l’α-alkylation de l’acétophénone par l’alcool benzylique. L’α-benzylation-méthylation croisée de l’acétophénone avec le méthanol et des alcools benzyliques a également été étudiée. L’α-benzylation du phénylacétonitrile par l’alcool benzylique a été mise en œuvre avec Ni/SiO2-Al2O3. Dans le cadre de la formation de liaisons C-N, ce catalyseur a aussi permis de réaliser la N-alkylation d’amides avec des alcools. Dans ce cas, une forte lixiviation du catalyseur en solution a été observée. Enfin, Ni/SiO2-Al2O3 s’est aussi révélé actif pour catalyser une réaction de couplage déshydrogénant sans accepteur d’hydrogène, permettant ainsi de synthétiser un indole à partir de l’aniline et d’un diol vicinal
A wide range of nucleophiles could be alkylated through borrowing hydrogen methodology using alcohols as low toxicity alkylating agents. Advantageously, the only byproduct of these high atom economy reactions is water. In this context, nickel supported on silica-alumina (65 wt% Ni/SiO2-Al2O3) was used to create C-C bonds, particularly to perform the α-alkylation of ketones with alcohols, of which methanol. The full characterization of this catalyst was made, before and after use. Ni/SiO2-Al2O3 was found to be recyclable over 5 runs for the α-alkylation of acetophenone with benzyl alcohol. The cross-benzylation-methylation of acetophenone with methanol and benzyl alcohols was also studied. The α-benzylation of phenylacetonitrile by benzyl alcohol was performed with Ni/SiO2-Al2O3. This catalyst was also able to catalyse the N-alkylation of amides with alcohols. In this case, an important leaching of the catalyst in solution was observed. Finally, Ni/SiO2-Al2O3 was also efficient to catalyze an acceptorless dehydrogenative coupling, allowing the synthesis of an indole from aniline and a vicinal diol
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Chapitres de livres sur le sujet "Indole N-alkylation"

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Taber, Douglass F. « The Bradshaw/Bonjoch Synthesis of (-)-Anominine ». Dans Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0097.

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The Hajos-Parrish cyclization was a landmark in the asymmetric construction of polycarbocyclic natural products. Impressive at the time, the proline-mediated intramolecular aldol condensation proceeded with an ee that was low by modern standards. Ben Bradshaw and Josep Bonjoch of the Universitat de Barcelona optimized this protocol, then used it to prepare (J. Am. Chem. Soc. 2010, 132, 5966) the enone 3 en route to the Aspergillus alkaloid (-)-anominine 4. The optimized catalyst for the enantioselective Robinson annulation was the amide 5 . With 2.5 mol % of the catalyst, the reaction proceeded in 97% ee. With only 1 mol % of catalyst, the reaction could be taken to 96% yield while maintaining the ee at 94%. Conjugate addition proceeded across the open face of 3 to give, after selective protection, the monoketal 7. After methylenation and deprotection, oxidation with IBX delivered the enone 9. With the angular quaternary centers of the natural product in place, the molecule became increasingly congested. Attempted direct alkylation of 9 led mainly to O-methylation. A solution to this problem was found in condensation with the Eschenmoser salt, followed by N-oxide formation and elimination to give the tetraene 10. Selective reduction by the Ganem protocol followed by equilibration completed the net methylation. Under anhydrous conditions, the oxide derived from the allylic selenide 12 did not rearrange. On the addition of water, the rearrangement proceeded smoothly. Protection and hydroboration converted 13 into 14. The bulk of the folded molecule protected the exo methylene of 14, so hydrogenation followed by protection and oxidation delivered 15. Conjugate addition of indole to 15 set the stage for oxidation and bis-methylenation to give 17. Selective Ru-mediated cross-coupling with 18 followed by deprotection then completed the synthesis of (-)-anominine 4, which proved to be the enantiomer of the natural product.
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Taber, Douglass. « Protection of Organic Functional Groups ». Dans Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0011.

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Several noteworthy new developments in the protection and deprotection of alcohols have been reported. Andrea Biffis of the Università di Padova has developed (Adv. Synth. Catal. 2007, 349, 2485) a Rh catalyst that effected silylation of alcohols such as 1 to the TES ether 2 at just 0.01% loading. Joshua Rokach of the Florida Institute of Technology has observed (Tetrahedron Lett. 2007, 48, 5289) that the reverse reaction, Rh-catalyzed desilylation of 3, was highly selective for the less congested site, even removing the usually less reactive TBS ether of 3 and leaving the more hindered TES ether. Hirokazu Tsukamoto of Tohoku University has devised (Tetrahedron Lett. 2007, 48, 8438) an improved procedure for the deprotection of allyl ethers such as 5. Filtration of the reaction mixture through polymer- bound diethanolamine removed > 95% of the Pd from the product. Patrick Pale of the Université Louis Pasteur has established (Tetrahedron Lett. 2007, 48, 8895) improved con- ditions for preparing diphenylmethyl ethers such as 10. The protecting group was removed with the Pd catalyst and ethanol. Amines can be activated for alkylation by N-formylation. Subsequent deformylation of the alkylated formamide 11 has been a challenge. Longqin Hu of Rutgers University has developed (Tetrahedron Lett . 2007, 48, 4585) microwave conditions that work well. Carbamates are stable, but esters are not. Protection of amides can also be important. Michael J. Zacuto of Merck Process in Rahway, NJ has optimized (J. Org. Chem. 2007, 72, 6298) the Rh-catalyzed deallylation of 13 to give 14. Carbonyl protection and deprotection is also important. Yoshihisa Kobayashi of the University of California, San Diego has devised (J. Org. Chem. 2007, 72, 3913) the isonitrile 15. Usually, the product 16 after Ugi condensation would be very difficult to hydrolyze. In the case of 16, mild acid effected cyclization to the acyl indole 17, which was easy to hydrolyze. In a different approach, Francesco Naso of the Università di Bari has shown (Chem. Commun. 2007, 3756) that acid chlorides such as 18 condensed with 19 to give the furan 20. Such furans are easily oxidized, liberating the starting acid.
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