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Journal articles on the topic 'Indole functionalization'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Sharma, Upendra, Inder Kumar, and Rakesh Kumar. "Recent Advances in the Regioselective Synthesis of Indoles via C–H Activation/Functionalization." Synthesis 50, no. 14 (2018): 2655–77. http://dx.doi.org/10.1055/s-0037-1609733.

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Indole is an important heterocyclic motif that occurs ubiquitously in bioactive natural products and pharmaceuticals. Immense efforts have been devoted to the synthesis of indoles starting from the Fisher indole synthesis to the recently developed C–H activation/functionalization-based methods. Herein, we have reviewed the progress made on the regioselective synthesis of functionalized indoles, including 2-substituted, 3-substituted and 2,3-disusbstituted indoles, since the year 2010.1 Introduction2 Metal-Catalyzed Synthesis of 2-Substituted Indoles3 Metal-Catalyzed Synthesis of 3-Substituted

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2

Chen, Jing-Biao, and Yi-Xia Jia. "Recent progress in transition-metal-catalyzed enantioselective indole functionalizations." Organic & Biomolecular Chemistry 15, no. 17 (2017): 3550–67. http://dx.doi.org/10.1039/c7ob00413c.

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Recent progress on the transition-metal-catalyzed enantioselective functionalization reaction of indoles is reviewed, which is mainly focused on asymmetric indole alkylations, arylations, cycloaddition reactions, and other reactions.

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3

Zhang, Yong-Sheng, Xiang-Ying Tang, and Min Shi. "Divergent synthesis of indole-fused polycycles via Rh(ii)-catalyzed intramolecular [3 + 2] cycloaddition and C–H functionalization of indolyltriazoles." Organic Chemistry Frontiers 2, no. 11 (2015): 1516–20. http://dx.doi.org/10.1039/c5qo00216h.

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4

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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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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5

Osipov, Sergey, and Daria Vorobyeva. "Selective Synthesis of 2- and 7-Substituted Indole Derivatives via Chelation-Assisted Metallocarbenoid C–H Bond Functionalization." Synthesis 50, no. 02 (2017): 227–40. http://dx.doi.org/10.1055/s-0036-1591498.

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Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid f

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6

Nagaraju, Karre, and Dawei Ma. "Oxidative coupling strategies for the synthesis of indole alkaloids." Chemical Society Reviews 47, no. 21 (2018): 8018–29. http://dx.doi.org/10.1039/c8cs00305j.

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7

Kaldas, Sherif J., Alexandre Cannillo, Terry McCallum, and Louis Barriault. "Indole Functionalization via Photoredox Gold Catalysis." Organic Letters 17, no. 11 (2015): 2864–66. http://dx.doi.org/10.1021/acs.orglett.5b01260.

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8

Pirovano, Valentina. "Gold-Catalyzed Functionalization Reactions of Indole." European Journal of Organic Chemistry 2018, no. 17 (2018): 1925–45. http://dx.doi.org/10.1002/ejoc.201800125.

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9

Wu, Wang, Zhang, and Jin. "Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins." Molecules 24, no. 21 (2019): 3944. http://dx.doi.org/10.3390/molecules24213944.

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The enantioselective transformations of indoles preferentially take place in the more-reactive azole ring. However, the methods for the enantioselective functionalization of the indole benzene ring are scarce. In this paper, a series of bifunctional (thio)urea derivatives were used to organocatalyze the enantioselective Friedel−Crafts hydroxyalkylation of indoles with isatins. The resulting products were obtained in good yields (65–90%) with up to 94% enantiomer excess (ee). The catalyst type and the substrate scope were broadened in this methodology.

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10

Cai, Yan, Yuming Li, Minxuan Zhang, Jiaxin Fu та Zhiwei Miao. "Regioselective BF3·Et2O-catalyzed C–H functionalization of indoles and pyrrole with reaction of α-diazophosphonates". RSC Advances 6, № 73 (2016): 69352–56. http://dx.doi.org/10.1039/c6ra15329a.

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A regioselective synthesis of β-(3-indol)-β-aminophosphonates and β-(2-pyrrol)-β-aminophosphonates was developed through an intermolecular C–H insertion of α-diazophosphonates with indole and pyrrole derivatives catalyzed by BF<sub>3</sub>·Et<sub>2</sub>O.

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11

Mo, Zu-Yu, Xin-Yu Wang, Yu-Zhen Zhang, Li Yang, Hai-Tao Tang, and Ying-Ming Pan. "Electrochemically enabled functionalization of indoles or anilines for the synthesis of hexafluoroisopropoxy indole and aniline derivatives." Organic & Biomolecular Chemistry 18, no. 20 (2020): 3832–37. http://dx.doi.org/10.1039/d0ob00157k.

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We have developed an efficient electrochemical method for selective functionalization of N-acetylindole or aniline derivatives with hexafluoroisopropanol to obtain a series of hexafluoroisopropoxy indoles and anilines.

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12

Xu, Lanting, Lushi Tan, and Dawei Ma. "Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group." Synlett 28, no. 20 (2017): 2839–44. http://dx.doi.org/10.1055/s-0036-1588530.

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An efficient rhodium-catalyzed method for C–H olefination at the C7 position of indoles has been developed. The N-imino directing group was shown to be crucial for high regioselectivity and reactivity of the metal catalyst. The utility of this protocol was further demonstrated through a concise, four-step synthesis of pyroquilon from indole.

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13

Serdyuk, Olga, Igor Trushkov, Maxim Uchuskin, and Vladimir Abaev. "Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds." Synthesis 51, no. 04 (2019): 787–815. http://dx.doi.org/10.1055/s-0037-1611702.

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Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefinatio

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14

Moriyama, Katsuhiko, Tsukasa Hamada, Kazuma Ishida, and Hideo Togo. "1,3-Iodo-amination of 2-methyl indoles via Csp2–Csp3 dual functionalization with iodine reagent." Chemical Communications 54, no. 34 (2018): 4258–61. http://dx.doi.org/10.1039/c8cc00352a.

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15

Iwao, Masatomo, and Tsutomu Fukuda. "Efficient Functionalization of Indole Ring via Regioselective Lithiations." Journal of Synthetic Organic Chemistry, Japan 60, no. 7 (2002): 691–700. http://dx.doi.org/10.5059/yukigoseikyokaishi.60.691.

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16

Szatmári, István, Judit Sas, and Ferenc Fülöp. "C-3 Functionalization of Indole Derivatives with Isoquinolines." Current Organic Chemistry 20, no. 20 (2016): 2038–54. http://dx.doi.org/10.2174/1385272820666160325202857.

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17

Kaldas, Sherif J., Alexandre Cannillo, Terry McCallum, and Louis Barriault. "ChemInform Abstract: Indole Functionalization via Photoredox Gold Catalysis." ChemInform 46, no. 43 (2015): no. http://dx.doi.org/10.1002/chin.201543172.

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18

Zhang, Wenzheng, Guangyang Xu, Lin Qiu, and Jiangtao Sun. "Gold-catalyzed C5-alkylation of indolines and sequential oxidative aromatization: access to C5-functionalized indoles." Organic & Biomolecular Chemistry 16, no. 21 (2018): 3889–92. http://dx.doi.org/10.1039/c8ob00826d.

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19

Gardner, Eric D., Dustin A. Dimas, Matthew C. Finneran, Sara M. Brown, Anthony W. Burgett, and Shanteri Singh. "Indole C6 Functionalization of Tryprostatin B Using Prenyltransferase CdpNPT." Catalysts 10, no. 11 (2020): 1247. http://dx.doi.org/10.3390/catal10111247.

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Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II and tubulin polymerization. However, the inability to perform late-stage modification of the indole ring has limited the structure–activity relationship studies of this class of natural products. Herein, we describe an efficient chemoenzymatic approach for the late-stage modification

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20

Beccalli, Egle M., Michael S. Christodoulou, Francesca Foschi, and Sabrina Giofrè. "Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives." Synthesis 52, no. 19 (2020): 2731–60. http://dx.doi.org/10.1055/s-0040-1707123.

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Palladium-catalyzed domino reactions are advanced tools in achieving various nitrogen-containing heterocycles in an efficient and economical manner due to the reduced number of steps in the process. This review highlights recent advances in domino processes aimed at the synthesis of indole derivatives and polycyclic systems containing the indole nucleus in intra/intra- or intra/intermolecular reactions. In particular, we consider domino processes that involve a double bond in a step of the sequence, which allow the issue of regioselectivity in the cyclization to be faced and overcome. The diff

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21

Dalpozzo, Renato. "Strategies for the asymmetric functionalization of indoles: an update." Chemical Society Reviews 44, no. 3 (2015): 742–78. http://dx.doi.org/10.1039/c4cs00209a.

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22

Messaoud, Mohamed Yacine Ameur, Ghenia Bentabed-Ababsa, Madani Hedidi, et al. "Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship." Beilstein Journal of Organic Chemistry 11 (August 24, 2015): 1475–85. http://dx.doi.org/10.3762/bjoc.11.160.

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The synthesis of N-arylated pyrroles and indoles is documented, as well as their functionalization by deprotonative metallation using the base in situ prepared from LiTMP and ZnCl2·TMEDA (1/3 equiv). With N-phenylpyrrole and -indole, the reactions were carried out in hexane containing TMEDA which regioselectively afforded the 2-iodo derivatives after subsequent iodolysis. With pyrroles and indoles bearing N-substituents such as 2-thienyl, 3-pyridyl, 4-methoxyphenyl and 4-bromophenyl, the reactions all took place on the substituent, at the position either adjacent to the heteroatom (S, N) or or

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23

Kumar, Pravin, Prajyot Jayadev Nagtilak, and Manmohan Kapur. "Transition metal-catalyzed C–H functionalizations of indoles." New Journal of Chemistry 45, no. 31 (2021): 13692–746. http://dx.doi.org/10.1039/d1nj01696b.

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This review summarises a wide range of transformations on the indole skeleton, including arylation, alkenylation, alkynylation, acylation, nitration, borylation, and amidation, using transition-metal catalyzed C–H functionalization as the key step.

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24

Song, Jinhua J., Jonathan T. Reeves, Daniel R. Fandrick, Zhulin Tan, Nathan K. Yee, and Chris H. Senanayake. "Construction of indole nucleus through C-H functionalization reactions." Arkivoc 2010, no. 1 (2010): 390–449. http://dx.doi.org/10.3998/ark.5550190.0011.110.

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25

Sar, Saibal, Ranajit Das, Dhiraj Barman, et al. "A sustainable C–H functionalization of indoles, pyrroles and furans under a blue LED with iodonium ylides." Organic & Biomolecular Chemistry 19, no. 35 (2021): 7627–32. http://dx.doi.org/10.1039/d1ob01219c.

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Pyrrole and indole derivatives are functionalized with the dimethyl malonate derived phenyl iodonium ylide in the presence of a blue LED via C–H functionalization of the respective heterocycles in methanol to generate the desired compounds.

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26

Sherikar, Mahadev Sharanappa, Raja Kapanaiah, Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "Rhodium(iii)-catalyzed C–H activation at the C4-position of indole: switchable hydroarylation and oxidative Heck-type reactions of maleimides." Chemical Communications 54, no. 79 (2018): 11200–11203. http://dx.doi.org/10.1039/c8cc06264a.

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A Rh(iii)-catalyzed C–H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF<sub>3</sub> group as a directing group.

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27

Broggini, Gianluigi, Egle M. Beccalli, Andrea Fasana, and Silvia Gazzola. "Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes." Beilstein Journal of Organic Chemistry 8 (October 11, 2012): 1730–46. http://dx.doi.org/10.3762/bjoc.8.198.

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This review highlights the development of palladium-catalyzed C–H and N–H functionalization reactions involving indole derivatives. These procedures require unactivated starting materials and are respectful of the basic principle of sustainable chemistry tied to atom economy.

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28

Cheng, Jian, Jun Sun, Jiekuan Yan, et al. "Carbene-Catalyzed Indole 3-Methyl C(sp3)–H Bond Functionalization." Journal of Organic Chemistry 82, no. 24 (2017): 13342–47. http://dx.doi.org/10.1021/acs.joc.7b02436.

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29

Miley, Galen P., Jennifer C. Rote, Richard B. Silverman, Neil L. Kelleher, and Regan J. Thomson. "Total Synthesis of Tambromycin Enabled by Indole C–H Functionalization." Organic Letters 20, no. 8 (2018): 2369–73. http://dx.doi.org/10.1021/acs.orglett.8b00700.

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30

Iwao, Masatomo, and Tsutomu Fukuda. "ChemInform Abstract: Efficient Functionalization of Indole Ring via Regioselective Lithiations." ChemInform 33, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.200248236.

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31

Petrini, Marino. "New Perspectives in the Indole Ring Functionalization using 2‐Indolylmethanols." Advanced Synthesis & Catalysis 362, no. 6 (2020): 1214–32. http://dx.doi.org/10.1002/adsc.201901245.

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32

Mishra, Neeraj Kumar, Miji Choi, Hyeim Jo, et al. "Direct C–H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis." Chemical Communications 51, no. 97 (2015): 17229–32. http://dx.doi.org/10.1039/c5cc07767b.

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33

Schollmeyer, Dieter, Young-Shin Kim, and Ulf Pindur. "Synthesis and Crystal Structures of Indole Derivatives and Indolo[2,3-a]carbazoles as Building Blocks to or as Protein Kinase C Inhibitors." Zeitschrift für Naturforschung B 52, no. 10 (1997): 1251–58. http://dx.doi.org/10.1515/znb-1997-1017.

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The functionalization reactions of 2,2’-bisindolyls with electrophiles and dienophiles gave rise to a group of new protein kinase C inhibitors. Rationalization of structure activity relationships and of some mechanistical aspects concerning the synthesis X ray crystal structures are described for 2,2’-bisindolyl derivatives 1-3 and 6 and for indolo[a]carbazoles 4 and 5.

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34

Lima, Rafaely N., José A. C. Delgado, Darlon I. Bernardi, et al. "Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation." Chemical Communications 57, no. 47 (2021): 5758–61. http://dx.doi.org/10.1039/d1cc01822a.

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35

Yang, Xing, Guoyong Luo, Liejin Zhou, et al. "Enantioselective Indole N–H Functionalization Enabled by Addition of Carbene Catalyst to Indole Aldehyde at Remote Site." ACS Catalysis 9, no. 12 (2019): 10971–76. http://dx.doi.org/10.1021/acscatal.9b03163.

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36

Radini, Ibrahim, Hussein El-Kashef, Norbert Haider, and Abdel-Rahman Farghaly. "Synthesis and functionalization of some new pyridazino[4,5-b]indole derivatives." Arkivoc 2016, no. 5 (2016): 101–17. http://dx.doi.org/10.3998/ark.5550190.p009.763.

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37

Feldman, Ken S., Inanllely Y. Gonzalez, and Jocelyn E. Brown. "Functionalization of 2-bromo-N-benzyl indole via lithium–bromide exchange." Tetrahedron Letters 56, no. 23 (2015): 3564–66. http://dx.doi.org/10.1016/j.tetlet.2015.01.032.

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38

Yu, Yi, Jun‐Song Zhong, Kai Xu, Yaofeng Yuan, and Ke‐Yin Ye. "Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives." Advanced Synthesis & Catalysis 362, no. 11 (2020): 2102–19. http://dx.doi.org/10.1002/adsc.201901520.

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39

Ma, Dengke, Zhihan Zhang, Min Chen, Zhenyang Lin, and Jianwei Sun. "Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp 3 )−H Bonds." Angewandte Chemie International Edition 58, no. 44 (2019): 15916–21. http://dx.doi.org/10.1002/anie.201909397.

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40

Ma, Dengke, Zhihan Zhang, Min Chen, Zhenyang Lin, and Jianwei Sun. "Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp 3 )−H Bonds." Angewandte Chemie 131, no. 44 (2019): 16063–68. http://dx.doi.org/10.1002/ange.201909397.

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41

Tayu, Masanori, Kazuya Nomura, Koki Kawachi, Kazuhiro Higuchi, Nozomi Saito, and Tomomi Kawasaki. "Direct C2-Functionalization of Indoles Triggered by the Generation of Iminium Species from Indole and Sulfonium Salt." Chemistry - A European Journal 23, no. 45 (2017): 10925–30. http://dx.doi.org/10.1002/chem.201702338.

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42

Ding, Yingcai, Wei Wu, Wannian Zhao, et al. "Generation of thioethers via direct C–H functionalization with sodium benzenesulfinate as a sulfur source." Organic & Biomolecular Chemistry 14, no. 4 (2016): 1428–31. http://dx.doi.org/10.1039/c5ob02073e.

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A novel ammonium iodide-induced sulfenylation method of flavones, indole and arylimidazo[1,2-a]pyridines using stable and odorless sodium benzenesulfinates as sulfur sources was developed, generating regioselective derivatives in good yields.

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43

Grenet, Erwann, Ashis Das, Paola Caramenti, and Jérôme Waser. "Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents." Beilstein Journal of Organic Chemistry 14 (May 25, 2018): 1208–14. http://dx.doi.org/10.3762/bjoc.14.102.

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The C–H indolation of heteroarenes was realized using the benziodoxolone hypervalent iodine reagents indoleBXs. Functionalization of the C–H bond in bipyridinones and quinoline N-oxides catalyzed by a rhodium complex allowed to incorporate indole rings into aza-heteroaromatic compounds. These new transformations displayed complete regioselectivity for the C-6 position of bipyridinones and the C-8 position of quinoline N-oxides and tolerated a broad range of functionalities, such as halogens, ethers, or trifluoromethyl groups.

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44

Bhattacharjee, Prantika, and Utpal Bora. "Organocatalytic dimensions to the C–H functionalization of the carbocyclic core in indoles: a review update." Organic Chemistry Frontiers 8, no. 10 (2021): 2343–65. http://dx.doi.org/10.1039/d0qo01466d.

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A review highlighting important research findings in remote C–H activation processes using effectual organocatalytic perspectives. The challenging indole carbocyclic ring positions were successfully accessed with proper regio- and stereocontrols.

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45

Lu, Beili, Xianyan Li, and Yongmei Lin. "Recent Development of Indole Synthesis by Transition Metal Catalyzed C—H Functionalization." Chinese Journal of Organic Chemistry 35, no. 11 (2015): 2275. http://dx.doi.org/10.6023/cjoc201505031.

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46

Leitch, Jamie A., Yunas Bhonoah, and Christopher G. Frost. "Beyond C2 and C3: Transition-Metal-Catalyzed C–H Functionalization of Indole." ACS Catalysis 7, no. 9 (2017): 5618–27. http://dx.doi.org/10.1021/acscatal.7b01785.

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47

Higuchi, Kazuhiro, Masanori Tayu та Tomomi Kawasaki. "Active thionium species mediated functionalization at the 2α-position of indole derivatives". Chemical Communications 47, № 23 (2011): 6728. http://dx.doi.org/10.1039/c1cc11645b.

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48

Sayyed, Iliyas Ali, Karolin Alex, Annegret Tillack, et al. "Selective reduction and functionalization of diethyl 1-alkyl-1H-indole-2,3-dicarboxylates." Tetrahedron 64, no. 20 (2008): 4590–95. http://dx.doi.org/10.1016/j.tet.2008.03.011.

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49

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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50

Zhang, Jun, Yun Hu, Haiyu Wang, et al. "Regioselective Functionalization of 4-Methyl-1H-indole for Scalable Synthesis of 2-Cyano-5-formyl-4-methyl-1H-indole." Organic Process Research & Development 22, no. 1 (2018): 97–102. http://dx.doi.org/10.1021/acs.oprd.7b00370.

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