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Journal articles on the topic 'Indole N-alkylation'

Author: Grafiati

Published: 14 March 2023

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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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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 (July 17, 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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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 (February 1, 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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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 (April 21, 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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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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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 KO^tBu.

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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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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, Andrus Metsala, Jaan Saame, Kristjan Kõster, Ivar Järving, Ivo Leito, and Tõnis Kanger. "Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis." Synthesis 52, no. 07 (November 26, 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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9

Huang, Bing-Bing, Liang Wu, Ren-Rong Liu, Ling-Ling Xing, Ren-Xiao Liang, and 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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10

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

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11

Bhagwat, Shripad S., and Candido Gude. "N-alkylation of indole ring using Mitsunobu reaction." Tetrahedron Letters 35, no. 12 (March 1994): 1847–50. http://dx.doi.org/10.1016/s0040-4039(00)73177-7.

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12

Shaikh, Iqbal N., Abdul Rahim, Shaikh Faazil, Syed Farooq Adil, Mohamed E. Assal, and Mohammad Rafe Hatshan. "BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies." Molecules 26, no. 8 (April 11, 2021): 2202. http://dx.doi.org/10.3390/molecules26082202.

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A simple and efficient BF3-OEt2 promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, 3w, having N,N-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC50 value 0.02 µM and 0.8 µM against HT-29 and Hepg2 cell lines, respectively, and compound 3i was most active amongst the series with IC50 value 1.5 µM against A549 cells. Molecular docking study and mechanism of reaction have briefly beendiscussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles.

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13

Cai, Yue, Qing Gu, and Shu-Li You. "Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid." Organic & Biomolecular Chemistry 16, no. 33 (2018): 6146–54. http://dx.doi.org/10.1039/c8ob01863d.

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14

Gharpure, Santosh J., and Santosh K. Nanda. "Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet–Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5586–90. http://dx.doi.org/10.1039/c6ob00501b.

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Thia-Pictet–Spengler cyclization is used for stereoselective synthesis of N-fused thiazinoindole derivatives. One-pot, sequential Friedel–Crafts alkylation – Pictet–Spengler cyclization and the synthesis of thiazino-oxepino-indole is developed.

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15

Singh, Anil K., and Abera Asefa. "N‐Alkylation of Indole Compounds in Modified Wittig–Horner Reaction." Synthetic Communications 37, no. 9 (May 2007): 1491–94. http://dx.doi.org/10.1080/00397910701229073.

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16

MEROUR, J. Y., and F. COSSAIS. "ChemInform Abstract: Regioselective N-Alkylation of Methyl Indole-2-carboxylate." ChemInform 24, no. 46 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199346113.

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17

Alexy, Eric J., Tyler J. Fulton, Haiming Zhang, and Brian M. Stoltz. "Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates." Chemical Science 10, no. 23 (2019): 5996–6000. http://dx.doi.org/10.1039/c9sc01726g.

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The first enantioselective Pd-catalyzed decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates generates acyclic all-carbon quaternary stereocenters in excellent yields (up to 99%) and enantioselectivities (up to 98% ee) using a new electron-deficient phosphinoxazoline (PHOX) ligand.

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18

Król, Marek, Grzegorz Ślifirski, Jerzy Kleps, Piotr Podsadni, Ilona Materek, Anna E. Kozioł, and Franciszek Herold. "The Synthesis and Absolute Configuration of Enantiomeric Pure (R)- and (S)-3-(piperidin-3-yl)-1H-Indole Derivatives." International Journal of Molecular Sciences 24, no. 1 (December 28, 2022): 517. http://dx.doi.org/10.3390/ijms24010517.

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This article describes the synthesis of new chiral 3-(piperidin-3-yl)-1H-indole derivatives (R)-10a-c and (S)-11a-c from the corresponding diastereomers: (3R, 2R) and (3S, 2R)-2-[3-(1H-indol-3-yl)-1-piperidyl]-2-phenyl-acetamides (3R, 2R)-4a, (3R, 2R)-6b, (3R, 2R)-8c and (3S, 2R)-5a, (3S, 2R)-7b, (3S, 2R)-9c. Diastereomers were obtained by N-alkylation of derivatives of racemic 3-(piperidin-3-yl)-1H-indoles 1a-c using (S)-2-(4-toluenesulfonyloxy)-phenylacetic amide (S)–II. The same method was applied to obtain (3R, 2S)-methyl-2-[3-(1H-indole-3-yl)-1-piperidyl]-2-phenylacetate (3R, 2S)-2a and (3S, 2S)-methyl-2-[3-(1H-indole-3-yl)-1-piperidyl]-2-phenylacetate (3S, 2S)-3a diastereomers by treating amine 1a with (R)-2-(4-toluenesulfonyloxy)-phenylacetic acid methylester (R)-I. Systematic studies via single crystal X-ray crystallography were used to determine the molecular structure of the racemates 1a-c and the absolute configuration of the enantiomers. The solid racemates 1b and 1c were “true racemates” crystallizing in a centrosymmetric space group, while 1a formed a racemic conglomerate of homoenantiomeric crystals. The absolute configuration was determined for the enantiomeric pairs (R)-10a/(S)-11a, (R)-10b/(S)-11b, and (R)-12c/(S)-13c, as well as for (3S,2S)-3a. Spectra of 1H, 13CNMR, HPLC, and HRMS for diastereomers and enantiomers were consistent with the determined structures.

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19

Karchava, A. V., I. S. Shuleva, A. A. Ovcharenko, and M. A. Yurovskaya. "2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions." Chemistry of Heterocyclic Compounds 46, no. 3 (July 2010): 291–301. http://dx.doi.org/10.1007/s10593-010-0504-3.

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20

Cohen, Peter A., and Louis A. Cohen. "Correlation of the effects of alkyl substituents on the basicities of indoles." Canadian Journal of Chemistry 70, no. 1 (January 1, 1992): 282–84. http://dx.doi.org/10.1139/v92-039.

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Alkyl groups at C-2 of indole increase basicity at the site of protonation, C-3, while alkyl groups at C-3 decrease basicity. These opposing effects can be incorporated, for both the isomeric mono- and 2,3-dialkylindoles, into a single linear free energy correlation, pKa = −10.05Σσ −3.94, in which [Formula: see text] and Ds is the double bond stabilization parameter at C-3. An analogous correlation for N-methylindoles, pKa = −8.64Σσ −2.80, reveals that the effect of N-alkylation on basicity is predictable but not additive. Keywords: alkylindoles, carbon basicity, free energy correlation, substituent effects, N-alkyl effect.

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21

Liu, Yanling, Xin Zhou, Deju Shang, Xiaohua Liu, and Xiaoming Feng. "N,N′-Dioxide–scandium(III) complex catalyzed highly enantioselective Friedel–Crafts alkylation of indole to alkylidene malonates." Tetrahedron 66, no. 7 (February 2010): 1447–57. http://dx.doi.org/10.1016/j.tet.2009.12.032.

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22

Itoh, Toshiyuki, Hiroyuki Uehara, Koji Ogiso, Shun Nomura, Shuichi Hayase, and Motoi Kawatsura. "Alkylation of N-Protecting Group-free Indole with Vinyl Ketones Using Iron Salt Catalyst." Chemistry Letters 36, no. 1 (January 2007): 50–51. http://dx.doi.org/10.1246/cl.2007.50.

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23

Trost, Barry M., Elumalai Gnanamani, and Chao-I. Joey Hung. "Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol." Angewandte Chemie International Edition 56, no. 35 (July 19, 2017): 10451–56. http://dx.doi.org/10.1002/anie.201705315.

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24

Trost, Barry M., Elumalai Gnanamani, and Chao-I. Joey Hung. "Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol." Angewandte Chemie 129, no. 35 (July 19, 2017): 10587–92. http://dx.doi.org/10.1002/ange.201705315.

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25

Liu, Yanling, Xin Zhou, Deju Shang, Xiaohua Liu, and Xiaoming Feng. "ChemInform Abstract: N,N′-Dioxide-Scandium(III) Complex Catalyzed Highly Enantioselective Friedel-Crafts Alkylation of Indole to Alkylidene Malonates." ChemInform 41, no. 24 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.201024107.

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26

Rossi, Sergio, Alessandra Puglisi, Laura Maria Raimondi, and Maurizio Benaglia. "Stereolithography 3D-Printed Catalytically Active Devices in Organic Synthesis." Catalysts 10, no. 1 (January 12, 2020): 109. http://dx.doi.org/10.3390/catal10010109.

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This article describes the synthesis of stereolithography (SLA) 3D-printed catalyst-impregnated devices and their evaluation in the organocatalyzed Friedel–Crafts alkylation of N–Me–indole with trans-β-nitrostyrene. Using a low-cost SLA 3D printer and freeware design software, different devices were designed and 3D-printed using a photopolymerizable resin containing a thiourea-based organocatalyst. The architectural control offered by the 3D-printing process allows a straightforward production of devices endowed with different shapes and surface areas, with high reproducibility. The 3D-printed organocatalytic materials promoted the formation of the desired product up to a 79% yield, although with longer reaction times compared to reactions under homogeneous conditions.

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27

Jorapur, Yogesh R., Jae Min Jeong, and Dae Yoon Chi. "Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids." Tetrahedron Letters 47, no. 14 (April 2006): 2435–38. http://dx.doi.org/10.1016/j.tetlet.2006.01.129.

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28

Mino, Takashi, Shingo Komatsu, Kazuya Wakui, Haruka Yamada, Hiroaki Saotome, Masami Sakamoto, and Tsutomu Fujita. "N-Aryl indole-derived C–N bond axially chiral phosphine ligands: synthesis and application in palladium-catalyzed asymmetric allylic alkylation." Tetrahedron: Asymmetry 21, no. 6 (April 2010): 711–18. http://dx.doi.org/10.1016/j.tetasy.2010.03.039.

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29

Gallo, Roger, and Mohamed Bourak. "Improving Regioselectivity under Phase Transfer Conditions: Effect of Chemical Parameters and Kinetic Study of Indole N-Alkylation." HETEROCYCLES 31, no. 3 (1990): 447. http://dx.doi.org/10.3987/com-88-4855.

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30

Hong, Liang, Wangsheng Sun, Chunxia Liu, Lei Wang, and Rui Wang. "Asymmetric Organocatalytic N-Alkylation of Indole-2-carbaldehydes with Î±,Î²-Unsaturated Aldehydes: One-Pot Synthesis of Chiral Pyrrolo[1,2-a]indole-2-carbaldehydes." Chemistry - A European Journal 16, no. 2 (January 11, 2010): 440–44. http://dx.doi.org/10.1002/chem.200902638.

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31

Hong, Liang, Wangsheng Sun, Chunxia Liu, Lei Wang, and Rui Wang. "Asymmetric Organocatalytic N-Alkylation of Indole-2-carbaldehydes with α,β-Unsaturated Aldehydes: One-Pot Synthesis of Chiral Pyrrolo[1,2-a]indole-2-carbaldehydes." Chemistry - A European Journal 16, no. 3 (January 14, 2010): 746. http://dx.doi.org/10.1002/chem.201090006.

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32

Kuvshinova, Sofya S., Yulia V. Nelyubina, Vladimir A. Larionov, Daria V. Vorobyeva, Sergey N. Osipov, and Dmitry A. Loginov. "Half-sandwich complexes of group 9 metals with N,Nʹ-ligands for CF3-carbenoid alkylation of N-(pyrimidin-2-yl)indole." Journal of Organometallic Chemistry 946-947 (August 2021): 121899. http://dx.doi.org/10.1016/j.jorganchem.2021.121899.

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33

Li, Nai-Kai, Jun-Qi Zhang, Bing-Bing Sun, Hai-Yan Li, and Xing-Wang Wang. "Chiral Diphosphine–Palladium-Catalyzed Sequential Asymmetric Double-Friedel–Crafts Alkylation and N-Hemiketalization for Spiro-polycyclic Indole Derivatives." Organic Letters 19, no. 8 (April 13, 2017): 1954–57. http://dx.doi.org/10.1021/acs.orglett.7b00368.

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34

Shi, Yan-Chao, Shou-Guo Wang, Qin Yin, and Shu-Li You. "N-alkylation of indole via ring-closing metathesis/isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis." Org. Chem. Front. 1, no. 1 (2014): 39–43. http://dx.doi.org/10.1039/c3qo00008g.

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35

Lodeiro, Carlos, Rufina Bastida, Emilia Bértolo, and Adolfo Rodríguez. "A new family of NxOy pyridine-containing macrocycles: Synthesis and characterization of their Y(III), Ln(III), Zn(II), and Cd(II) coordination compounds." Canadian Journal of Chemistry 82, no. 3 (March 1, 2004): 437–47. http://dx.doi.org/10.1139/v03-214.

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Reaction between 2,6-bis(2-formylphenoxymethyl)pyridine and N,N-bis(3-aminopropyl)methylamine or tris(2-aminoethyl)amine has been used as the starting point for the synthesis of seven oxa-aza macrocyclic ligands, five of them never reported previously. They all feature different pendant arms, which provide a wide range of coordination possibilities. The Schiff base macrocycles L1 and L4 and their reduced ligands L2 and L5 are derived from 2,6-bis(2-formylphenoxymethyl)pyridine and tris(2-aminoethyl)amine or N,N-bis(3-aminopropyl)methylamine, respectively. The reaction of L1 with salicylaldehyde forms L3, which features an imine bond in the pendant arm. The ligand L5 has been the precursor for the pendant-armed L6 and L7, by alkylation of the free NH groups with methyl-imidazole or methyl-indole. By a template or a nontemplate approach, we have synthesized different mono- and dinuclear complexes with Y(III), Ln(III), Zn(II), and Cd(II) cations. Both the free macrocyclic ligands and their corresponding metal complexes have been characterized by microanalysis, IR, UVvis, 1H and 13C NMR spectroscopy, FAB mass spectrometry, MS electrospray, and conductivity measurements.Key words: Schiff-base macrocycle, template synthesis, macrocyclic ligand complexes, lanthanide(III) complexes.

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36

Harkov, Stefan. "SYNTHESIS AND CONVERSION OF NEW POTENTIALLY BIOLOGICALLY ACTIVE 4-THIAZOLIDINONE DERIVATIVES WITH A TRIAZINOINDOLE FRAGMENT IN THE MOLECULES." KNOWLEDGE - International Journal 54, no. 4 (September 30, 2022): 677–81. http://dx.doi.org/10.35120/kij5404677h.

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A wide spectrum of biological activity and the possibility of diverse chemical modification of isatinderivatives prompts the search for new highly active compounds as potential drugs among condensed and noncondensedheterocyclic systems containing the specified molecular "matrix". Studies of 1,2,4-triazino[5,6-b]indoles,the chemical precursors of which are isatins, have shown the prospect of their use in the treatment of oncologicaldiseases. In addition, potential antifungal, antiviral, antihypertensive agents have been identified among thesederivatives.Adhering to the main synthetic strategy of our research, which is based on the "hybrid-pharmacophoric" approach inthe synthesis of new heterocyclic derivatives of 4-thiazolidinone, in our opinion, the combination of the mainscaffold (4-thiazolidinone) and the structural "imitator" is interesting and promising of the isatin "matrix" -triazinoindole fragment, as well as the synthesis of new polyheterocyclic ensembles, including those with apharmacologically attractive pyrazoline fragment. Under the conditions of the S-alkylation reaction of 3-mercapto-5H-1,2,4-triazino[5,6-b]indoles, 2-chloro-1-(3,5-diaryl-4,5-dihydropyrazole- 1-yl)ethanones, which made it possibleto obtain 1,2,4-triazino[5,6-b]indole-pyrazolines with preparative yields. By hydrazinolysis of 3-mercapto-5H-1,2,4-triazino[5,6-b]indoles, corresponding hydrazines were obtained, which were successfully used for the first time inthe Holmberg reaction, and derivatives of the triazinoindole-thiazolidinone system were obtained – 3-(1,2 ,4-triazino[5,6-b]indol-3-ylamino-2-thioxothiazolidin-4-ones Chemical modification of methylene-active compoundswas carried out under the conditions of the Kniovenagel reaction with aromatic aldehydes and isatin derivatives,which was substantiated by the results of biological studies of structurally related heteryl-substituted 5-ylidenerhodanines. The synthesis of derivatives of the 4-thiazolidinone-thiadiazinoindole system, which is based onthe interaction of N-(1,3,4-thiadiazinoindol-2-yl)-2-chloroacetamides with ammonium thiocyanate in an acetonemedium, was carried out. The obtained conjugates are methylene-active compounds, which made it possible tosynthesize a series of 5-arylidene derivatives under the conditions of the Kniovenagel reaction. The purpose of thework is to experimentally confirm or refute the feasibility of chemical modification of isatin into the triazineindolinesystem and its combination with 4-thiazolidinone biophore for the search of new biologically activecompounds, including highly active antitumor agents. The structure of the synthesized compounds was confirmedby NMR spectroscopy. To study the structure in the solid state, the IR spectra of the key compounds in KBr tabletswere studied.

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37

Wang, Shuai, Yao-Bin Shen, Long-Fei Li, Bin Qiu, Liping Yu, Qing Liu, and Jian Xiao. "N-Alkylation-Initiated Redox-Neutral [5 + 2] Annulation of 3-Alkylindoles with o-Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines." Organic Letters 21, no. 22 (November 7, 2019): 8904–8. http://dx.doi.org/10.1021/acs.orglett.9b03011.

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38

BHAGWAT, S. S., and C. GUDE. "ChemInform Abstract: Thromboxane Receptor Antagonism Combined with Thromboxane Synthase Inhibition. Part 8. N-Alkylation of the Indole Ring Using the Mitsunobu Reaction." ChemInform 25, no. 30 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199430115.

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39

Bora, Darshana, Stephy Elza John, Mary Sravani Galla, Manda Sathish, and Nagula Shankaraiah. "Rh(III)-catalysed site-selective alkylation of β-carbolines/isoquinolines and tandem C H/C N functionalization to construct indolizine-indole frameworks." Molecular Catalysis 533 (December 2022): 112783. http://dx.doi.org/10.1016/j.mcat.2022.112783.

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40

Mayer, Szabolcs, András Keglevich, Csilla Sepsey Für, Hedvig Bölcskei, Viktor Ilkei, Péter Keglevich, and László Hazai. "Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids." Chemistry 2, no. 3 (August 10, 2020): 714–26. http://dx.doi.org/10.3390/chemistry2030046.

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The antitumor indole–indoline alkaloids of the evergreen Catharanthus roseus—namely vinblastine and vincristine—are widely used in chemotherapy of cancer. Many efforts were made to synthesize more efficient derivatives with less side-effect. The 14,15-cyclopropane derivative of vinblastine was synthesized successfully by a five-step procedure starting from vindoline. Vincristine, vinorelbine and several derivatives condensed with a cyclopropane ring were synthesized. Various hybrid molecules were prepared by the coupling reaction of vindoline and methyl ester of tryptophan, which were conjugated by carrier peptides of octaarginine. Studying the halogenation reactions of vindoline and catharanthine some fluorine derivatives were obtained which showed promising antitumor activity on various tumor types. The synthesis of the Aspidospermane alkaloid bannucine and 5′-epibannucine were carried out using N-acyliminium intermediates. The same intermediate was also applied in the first synthesis of sessiline. The research group have synthesized of flavonoid alkaloids: dracocephins A and B. Further three flavonoid alkaloids, namely 8-(2”-pyrrolidinon-5′′-yl)quercetin, 6-(2′′-pyrrolidinon-5′′-yl)-(−)- and 8-(2′′-pyrrolidinon-5′′-yl)-(−)-epicatechin were prepared by acid-catalyzed regioselective Mannich reaction starting from the corresponding flavonoid precursor. Vindoline was also coupled to synthetic pharmacophores, such as triphenylphosphine and various N-heterocycles. Some of these hybrid molecules showed significant antitumor activity. Furthermore, 7-OH and 7-NH modified flavonoid derivatives were synthesized by a regioselective alkylation followed by Smiles rearrangement and hydrolysis.

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Mottinelli, Marco, Mathew P. Leese, and Barry V. L. Potter. "Accessing simply-substituted 4-hydroxytetrahydroisoquinolines via Pomeranz–Fritsch–Bobbitt reaction with non-activated and moderately-activated systems." Beilstein Journal of Organic Chemistry 13 (September 6, 2017): 1871–78. http://dx.doi.org/10.3762/bjoc.13.182.

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Background: 1,2,3,4-Tetrahydroisoquinolines (THIQs) are common motifs in alkaloids and in medicinal chemistry. Synthetic access to THIQs via the Pomeranz–Fritsch–Bobbit (PFB) methodology using mineral acids for deactivated, electron-poor aromatic systems, is scarcely represented in the literature. Here, the factors controlling the regiochemical outcome of cyclization are evaluated. Results: A double reductive alkylation was telescoped into a one-pot reaction delivering good to excellent yields of desired aminoacetals for cyclization. Cyclization of activated systems proceeded smoothly under standard PFB conditions, but for non-activated systems the use of HClO4 alone was effective. When cyclization was possible in both para- and ortho-positions to the substituent, 7-substituted derivatives were formed with significant amounts of 5-substituted byproduct. The formation of the 4-hydroxy-THIQs vs the 4-methoxy-THIQ products could be controlled through modification of the reaction concentration. In addition, while a highly-activated system exclusively cyclized to the indole, this seems generally highly disfavored. When competition between 6- and 7-ring formation was investigated in non-activated systems, 5,7,8,13-tetrahydro-6,13-methanodibenzo[c,f]azonine was exclusively obtained. Furthermore, selective ring closure in the para-position could be achieved under standard PFB conditions, while a double ring closure could be obtained utilizing HClO4. Conclusion: Reactivity differences in aminoacetal precursors can be employed to control cyclization using the PFB methodology. It is now possible to select confidently the right conditions for the synthesis of N-aryl-4-hydroxy-1,2,3,4-tetrahydroisoquinolines.

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Crich, David, and Xianhai Huang. "ChemInform Abstract: Reaction of Tryptophan Derivatives with N-Phenylselenyl Phthalimide: The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-b]indole Products. Alkylation of Tryptophan with Inversion of Configuration." ChemInform 31, no. 2 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200002192.

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Ling, Li, Jing Cao, Jianfeng Hu, and Hao Zhang. "Copper-catalyzed N-alkylation of indoles by N-tosylhydrazones." RSC Advances 7, no. 45 (2017): 27974–80. http://dx.doi.org/10.1039/c7ra03765a.

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Gao, Yadong, Jianhua Li, Songlin Bai, Daoquan Tu, Chao Yang, Zhiwen Ye, Bingcheng Hu, Xiangbing Qi, and Chao Jiang. "Direct synthesis of annulated indoles through palladium-catalyzed double alkylations." Organic Chemistry Frontiers 7, no. 9 (2020): 1149–57. http://dx.doi.org/10.1039/d0qo00135j.

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Chen, Jian-Ping, Wen-Wen Chen, Yi Li, and Ming-Hua Xu. "A highly diastereoselective Friedel–Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3363–70. http://dx.doi.org/10.1039/c5ob00063g.

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Siddiki, S. M. A. Hakim, Kenichi Kon, and Ken-ichi Shimizu. "Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst." Green Chemistry 17, no. 1 (2015): 173–77. http://dx.doi.org/10.1039/c4gc01419g.

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Mino, Takashi, Kenji Nishikawa, Moeko Asano, Yamato Shima, Toshibumi Ebisawa, Yasushi Yoshida, and Masami Sakamoto. "Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7509–19. http://dx.doi.org/10.1039/c6ob01354f.

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Fink, David M. "Cesium Carbonate Promoted N-Alkylation of Indoles." Synlett, no. 13 (2004): 2394–96. http://dx.doi.org/10.1055/s-2004-832836.

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Zhang, Lvye, Binqiang Wu, Zhangtao Chen, Jinjin Hu, Xiaofei Zeng, and Guofu Zhong. "Chiral phosphoric acid catalyzed enantioselective N-alkylation of indoles with in situ generated cyclic N-acyl ketimines." Chemical Communications 54, no. 66 (2018): 9230–33. http://dx.doi.org/10.1039/c8cc05073b.

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A chiral SPINOL derived phosphoric acid-catalyzed asymmetric N-alkylation reaction of indoles with cyclic α-diaryl-substituted N-acyl imines, which are generated in situ from 3-aryl 3-hydroxyisoindo-linones, has been demonstrated.

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Hu, Miao, Yong Jiang, Nan Sun, Baoxiang Hu, Zhenlu Shen, Xinquan Hu, and Liqun Jin. "Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen strategy." New Journal of Chemistry 45, no. 22 (2021): 10057–62. http://dx.doi.org/10.1039/d1nj01581h.

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