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Bibliografie tematiche / Indole N-alkylation

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Articoli di riviste

Letteratura scientifica selezionata sul tema "Indole N-alkylation"

Autore: Grafiati

Pubblicato: 14 marzo 2023

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Articoli di riviste sul tema "Indole N-alkylation"

1

Yi, Zi-Juan, Jian-Ting Sun, Tian-Yu Yang, Xian-Yong Yu, Xiao-Li Han, and 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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Abstract (sommario):

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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2

Trubitsõn, Dmitri, and Tõnis Kanger. "Enantioselective Catalytic Synthesis of N-alkylated Indoles." Symmetry 12, no. 7 (2020): 1184. http://dx.doi.org/10.3390/sym12071184.

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Abstract (sommario):

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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3

Gardette, Daniel, Jean-Claude Gramain, Marie-Eve Lepage, and Yves Troin. "Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons." Canadian Journal of Chemistry 67, no. 2 (1989): 213–19. http://dx.doi.org/10.1139/v89-036.

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Abstract (sommario):

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: photocycliz

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4

Qiu, Zhongxuan, Rui Sun, Kun Yang, and 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 (2019): 1575. http://dx.doi.org/10.3390/molecules24081575.

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Abstract (sommario):

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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5

Wang, Chengyuan, Zhuopeng Li, Jiong Zhang, and 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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6

Kumar, Nivesh, Arindam Maity, Vipin R. Gavit, and 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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Abstract (sommario):

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(PPh<sub>3</sub>)<sub>4</sub> in the presence of 1.2 equivalent of both triethylborane and KO<sup>t</sup>Bu.

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7

Ding, Zhenhua, and Naohiko Yoshikai. "C2-Alkylation of N-pyrimidylindole with vinylsilane via cobalt-catalyzed C–H bond activation." Beilstein Journal of Organic Chemistry 8 (September 14, 2012): 1536–42. http://dx.doi.org/10.3762/bjoc.8.174.

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Abstract (sommario):

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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8

Trubitsõn, Dmitri, Jevgenija Martõnova, Kristin Erkman, et al. "Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis." Synthesis 52, no. 07 (2019): 1047–59. http://dx.doi.org/10.1055/s-0039-1690751.

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Abstract (sommario):

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 cinch

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9

Huang, Bing-Bing, Liang Wu, Ren-Rong Liu, Ling-Ling Xing, Ren-Xiao Liang та Yi-Xia Jia. "Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters". Organic Chemistry Frontiers 5, № 6 (2018): 929–32. http://dx.doi.org/10.1039/c7qo01014a.

Testo completo

Abstract (sommario):

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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10

Mérour, J. Y., and F. Cossais. "Regioselective N-Alkylation of Methyl Indole-2-carboxylate." Synthetic Communications 23, no. 13 (1993): 1813–20. http://dx.doi.org/10.1080/00397919308011281.

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