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Journal articles on the topic 'Arylindoles'

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1

Kwon, Yongseok, and Ahreum Kim. "Catalytic Atroposelective Dynamic Kinetic Resolution of Substituted Indoles." Synlett 33, no. 03 (2021): 201–6. http://dx.doi.org/10.1055/a-1694-4695.

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AbstractAdvances in asymmetric catalysis have led to enormous progress in the atroposelective synthesis of axially chiral biaryls. Because of the biological importance of indoles, stereogenic axes in aryl-substituted indoles have attracted considerable research attention in recent years. Here we present a summary of recent advances in the atroposelective synthesis of aryl-substituted indoles by dynamic kinetic resolution. Although several researchers have developed enantioselective syntheses of 3-arylindoles, N-arylindoles have been much less studied. Accordingly, we have developed a Pictet–Sp
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2

Li, Bin, Beibei Zhang, Xinying Zhang та Xuesen Fan. "Regio-selective synthesis of diversely substituted benzo[a]carbazoles through Rh(iii)-catalyzed annulation of 2-arylindoles with α-diazo carbonyl compounds". Chemical Communications 53, № 7 (2017): 1297–300. http://dx.doi.org/10.1039/c6cc08377c.

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A novel synthetic approach toward benzo[a]carbazoles and 6-aminobenzo[a]carbazoles containing an unprotected NH unit through Rh(iii)-catalyzed cascade reactions of 2-arylindoles or 2-arylindole-3-carbonitriles with α-diazo carbonyl compounds is presented.
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3

Yuan, Xi, Xudong Wu, Fei Peng, Haijun Yang, Changjin Zhu, and Hua Fu. "Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality." Chemical Communications 56, no. 83 (2020): 12648–51. http://dx.doi.org/10.1039/d0cc05432a.

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An efficient method for chiral phosphoric acid-catalyzed asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality has been developed via the reaction of 3-arylindoles with 2-aryl-3H-indol-3-ones.
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4

Arcadi, Antonio, Sandro Cacchi, Giancarlo Fabrizi, et al. "Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization withN,N-dimethylformamide dimethyl acetal." Beilstein Journal of Organic Chemistry 14 (September 14, 2018): 2411–17. http://dx.doi.org/10.3762/bjoc.14.218.

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An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2-c]quinazolines is described. The Pd-catalyzed reaction ofo-(o-aminophenylethynyl) trifluoroacetanilides with Ar–B(OH)2afforded 2-(o-aminophenyl)-3-arylindoles, that were converted to 12-arylindolo[1,2-c]quinazolines by adding dimethylformamide dimethyl acetal (DMFDMA) to the reaction mixture after extractive work-up. This reaction outcome is different from the previously reported Pd-catalyzed sequential reaction of the same substrates with Ar–I, Ar–Br and ArN2+BF4−, that afforded 12-arylindolo[1,2-c]quinazolin-6(5H)-ones. Mo
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5

Oeser, Petr, Jakub Koudelka, Artem Petrenko, and Tomáš Tobrman. "Recent Progress Concerning the N-Arylation of Indoles." Molecules 26, no. 16 (2021): 5079. http://dx.doi.org/10.3390/molecules26165079.

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.
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6

Li, Xu-Qin, Xian-Xing Shang, and Huu-Manh Vu. "One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant." Synthesis 50, no. 02 (2017): 377–83. http://dx.doi.org/10.1055/s-0036-1590933.

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A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc)2] and assisted by water. PhI(OAc)2 was used as the sole oxidant and water was a crucial additive. Our preliminary mechanistic investigations suggest that a water-involved, iodine(III)-promoted sequential oxidation of 2-arylindoles, which was terminated by an interesting Grob-type fragmentation of a fused tricyclic precursor, might be the main components of this one-pot transformation.
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7

T., V. Sravanthi, and L. Manju S. "An improved Bischler indole synthesis to obtain 2-arylindole scaffolds." Journal of Indian Chemical Society Vol. 92, Jun 2015 (2015): 843–46. https://doi.org/10.5281/zenodo.5631174.

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Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore-632 014, Tamilnadu, India <em>E-mail </em>: slmanju@vit.ac.in In this paper, an economical and improved Bischler indole method to obtain 2-arylindoles in a single step without any catalyst under thermal condition is described. Reaction between &alpha;-bromoarylethanones (1 equi.) and aniline (1 equi.) on reflux in dimethylformamide afforded 2-arylindoles in 85&ndash;90% yield within 20 min. All the synthesized 2- aryl indoles were characterized by spectral analyses such as FT-IR, GC-MS and NMR techniques.
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8

Nipate, Dhananjay S., Vikki N. Shinde, Krishnan Rangan, and Anil Kumar. "Switchable regioselective hydroalkylation of 2-arylindoles with maleimides." Organic & Biomolecular Chemistry 19, no. 22 (2021): 4910–21. http://dx.doi.org/10.1039/d1ob00690h.

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9

Liu, Congrong, Lianghui Ding, Guang Guo, Weiwei Liu, and Fu-Lai Yang. "Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides." Organic & Biomolecular Chemistry 14, no. 10 (2016): 2824–27. http://dx.doi.org/10.1039/c5ob02569a.

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10

Yu, Shuling, Kun Hu, Julin Gong, et al. "Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles." Organic & Biomolecular Chemistry 15, no. 20 (2017): 4300–4307. http://dx.doi.org/10.1039/c7ob00572e.

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11

Yuan, Zihang, Shouxiong Chen, and Zhiqiang Weng. "Copper-catalyzed synthesis of trifluoromethylated bis(indolyl)arylmethanes from 2-arylindoles and 2,2,2-trifluoroacetohydrazide." Organic Chemistry Frontiers 7, no. 3 (2020): 482–86. http://dx.doi.org/10.1039/c9qo01131e.

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12

Qu, Chuanhua, Songlin Zhang, Hongbin Du, and Chengjian Zhu. "Cascade photoredox/gold catalysis: access to multisubstituted indoles via aminoarylation of alkynes." Chemical Communications 52, no. 100 (2016): 14400–14403. http://dx.doi.org/10.1039/c6cc08478h.

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13

Jang, Su San, та So Won Youn. "The cooperative FeCl3/DDQ system for the regioselective synthesis of 3-arylindoles from β-monosubstituted 2-alkenylanilines". Organic & Biomolecular Chemistry 14, № 7 (2016): 2200–2204. http://dx.doi.org/10.1039/c6ob00074f.

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14

Smith, Andrew J., Daniela Dimitrova, Jude N. Arokianathar, et al. "New reductive rearrangement of N-arylindoles triggered by the Grubbs–Stoltz reagent Et3SiH/KOtBu." Chemical Science 11, no. 14 (2020): 3719–26. http://dx.doi.org/10.1039/d0sc00361a.

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15

Jiang, Shuai-Shuai, Yu-Ting Xiao, Yan-Chen Wu, Shu-Zheng Luo, Ren-Jie Song, and Jin-Heng Li. "Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides." Organic & Biomolecular Chemistry 18, no. 25 (2020): 4843–47. http://dx.doi.org/10.1039/d0ob00877j.

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16

Xu, Meng-Meng, Wen-Bin Cao, Xiao-Ping Xu, and Shun-Jun Ji. "Efficient synthesis of 2-arylquinazolin-4-amines via a copper-catalyzed diazidation and ring expansion cascade of 2-arylindoles." Chemical Communications 54, no. 89 (2018): 12602–5. http://dx.doi.org/10.1039/c8cc07721e.

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17

Reiser, Oliver, Inga Prediger, and Torsten Weiss. "Facile Access to 2-Arylindolines and 2-Arylindoles by Microwave-Assisted Tandem Radical Cyclization." Synthesis 2008, no. 14 (2008): 2191–98. http://dx.doi.org/10.1055/s-2008-1067154.

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18

Zhang, Zhenhui, Kunkun Liu, Xun Chen, Shi-Jian Su, Yuanfu Deng, and Wei Zeng. "Rhodium(iii)-catalyzed indole-directed carbenoid aryl C–H insertion/cyclization: access to 1,2-benzocarbazoles." RSC Advances 7, no. 49 (2017): 30554–58. http://dx.doi.org/10.1039/c7ra04889k.

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19

Black, DS, MC Bowyer, PK Bowyer, et al. "Synthesis of Activated 3-Arylindoles." Australian Journal of Chemistry 47, no. 9 (1994): 1741. http://dx.doi.org/10.1071/ch9941741.

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A wide range of substituted 3-aryl-4,6-dimethoxyindoles (6) has been synthesized from the related α-anilinoacetophenones (5), in which the nitrogen atom is protected by a trifluoroacetyl or acetyl group. This method has led to the synthesis of a 3,7′-biindolyl (12).
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20

Walkup, R. E., and J. Linder. "2-Formylation of 3-arylindoles." Tetrahedron Letters 26, no. 18 (1985): 2155–58. http://dx.doi.org/10.1016/s0040-4039(00)98949-4.

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21

Gogrichiani, �. O., I. Sh Chikvaidze, L. I. Dzhibladze, M. B. Tsotadze, Sh A. Samsoniya, and N. N. Suvorov. "Synthesis of some new arylindoles." Chemistry of Heterocyclic Compounds 30, no. 10 (1994): 1170–73. http://dx.doi.org/10.1007/bf01184879.

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22

Lu, Fo-Yun, Yu-Jue Chen, Yuan Chen, Xuan Ding, Zhi Guan, and Yan-Hong He. "Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones." Chemical Communications 56, no. 4 (2020): 623–26. http://dx.doi.org/10.1039/c9cc09178e.

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23

Goggiamani, Antonella, Sandro Cacchi, Giancarlo Fabrizi, Antonia Iazzetti, and Rosanna Verdiglione. "2-(Aminomethyl)-3-arylindoles from 3-(o-Trifluoroacetamidoaryl)-1-propargylic Alcohols, Aryl Halides, and Amines: A Domino Palladium-Catalyzed Three-Component Approach." Synthesis 49, no. 18 (2017): 4163–72. http://dx.doi.org/10.1055/s-0036-1589016.

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24

Uruvakili, Anasuyamma, and K. C. Kumara Swamy. "Gold catalysed transformation of 2-arylindoles to terphenyl amines via 3-dienyl indoles and Brønsted acid promoted formation of 2-carboxyindoles to 3-indenylindoles via 3-allenylindoles." Organic & Biomolecular Chemistry 17, no. 12 (2019): 3275–84. http://dx.doi.org/10.1039/c9ob00232d.

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25

Patel, Om P. S., Shiv Dhiman, Shahid Khan, et al. "A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity." Organic & Biomolecular Chemistry 17, no. 24 (2019): 5962–70. http://dx.doi.org/10.1039/c9ob00797k.

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26

Qin, Yao, Weihui Zhuang, Xiemin Guo, Xiaofeng Zhang, and Qiufeng Huang. "Rhodium-catalyzed direct C H amination of 2-arylindoles and 7-arylindoles with free amines." Tetrahedron Letters 62 (January 2021): 152686. http://dx.doi.org/10.1016/j.tetlet.2020.152686.

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27

Ban, Kazuho, Yuta Yamamoto, Hironao Sajiki, and Yoshinari Sawama. "Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons." Organic & Biomolecular Chemistry 18, no. 20 (2020): 3898–902. http://dx.doi.org/10.1039/d0ob00702a.

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28

Xu, Chuangchuang, Wenlai Xie, and Jiaxi Xu. "Metal-free and regiospecific synthesis of 3-arylindoles." Organic & Biomolecular Chemistry 18, no. 14 (2020): 2661–71. http://dx.doi.org/10.1039/d0ob00317d.

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A microwave-assisted acid and base co-catalyzed strategy shows high efficiency in the synthesis of 3-arylindoles through tandem nucleophilic ring-opening and Fischer indolization of aryloxiranecarbonitriles and arylhydrazine hydrochlorides.
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29

Kale, Ajit Prabhakar, Gangam Srikanth Kumar та Manmohan Kapur. "Palladium-catalyzed synthesis of 2-alkenyl-3-arylindoles via a dual α-arylation strategy: formal synthesis of the antilipemic drug fluvastatin". Organic & Biomolecular Chemistry 13, № 45 (2015): 10995–1002. http://dx.doi.org/10.1039/c5ob01632k.

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30

Lintott, Mia, and Alexis Perry. "Straightforward synthesis of N-arylindoles via one-pot Fischer indolisation–indole N-arylation." RSC Advances 13, no. 23 (2023): 15993–97. http://dx.doi.org/10.1039/d3ra02658b.

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One-pot, microwave-promoted Fischer indolisation–indole N-arylation enables straightforward, rapid synthesis of structurally-diverse N-arylindoles from widely-available precursors, using a simple, air-stable catalyst in a common, sustainable solvent.
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31

Li, Bin, Chenhao Guo, Nana Shen, Xinying Zhang, and Xuesen Fan. "Synthesis of maleimide fused benzocarbazoles and imidazo[1,2-a]pyridines via rhodium(iii)-catalyzed [4 + 2] oxidative cycloaddition." Organic Chemistry Frontiers 7, no. 22 (2020): 3698–704. http://dx.doi.org/10.1039/d0qo01109f.

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In this paper, an efficient and sustainable synthesis of maleimide-fused benzocarbazoles/imidazo[1,2-a]pyridines from the reaction of 2-arylindoles/2-arylimidazo[1,2-a]pyridines with maleimides through oxidative [4 + 2] annulation is presented.
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32

Xu, Haopeng, Chao Pi, Yangjie Wu та Xiuling Cui. "Three-component synthesis of α-indole-β-sulfonyl tetrahydrofurans under metal-free conditions". New Journal of Chemistry 46, № 5 (2022): 2239–44. http://dx.doi.org/10.1039/d1nj05749a.

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An efficient multi-component reaction has been developed for the synthesis of 2,3-disubstituted tetrahydrofurans in a “one pot” manner, starting from readily available 2-arylindoles, arylsulfonyl azides, and tetrahydrofuran under simple and easily operated reaction conditions.
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33

Hfaiedh, Anoir, Hamed Ben Ammar, Jean-François Soulé, and Henri Doucet. "Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides." Organic & Biomolecular Chemistry 14, no. 21 (2016): 4947–56. http://dx.doi.org/10.1039/c6ob00584e.

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Halo-substituents at the indolyl C3 position act as temporary blocking groups allowing the regioselective formation of 2-arylindoles through a direct desulfitative arylation. This method allows one to prepare a wide variety of indole derivatives in a few steps.
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34

GOGRICHIANI, E. O., I. SH CHIKVAIDZE, L. I. DZHIBLADZE, M. B. TSOTADZE, SH A. SAMSONIYA, and N. N. SUVOROV. "ChemInform Abstract: Synthesis of Some New Arylindoles." ChemInform 26, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199528116.

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35

BLACK, D. ST C., M. C. BOWYER, P. K. BOWYER, et al. "ChemInform Abstract: Synthesis of Activated 3-Arylindoles." ChemInform 26, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.199504167.

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36

Yin, Zhiping, Zechao Wang, and Xiao-Feng Wu. "Iron-Catalyzed Regioselective Synthesis of 3-Arylindoles." ChemistrySelect 2, no. 23 (2017): 6689–92. http://dx.doi.org/10.1002/slct.201701530.

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37

Murru, Siva, August A. Gallo, and Radhey S. Srivastava. "Copper-Catalyzed Direct Synthesis of 3-Arylindoles." European Journal of Organic Chemistry 2011, no. 11 (2011): 2035–38. http://dx.doi.org/10.1002/ejoc.201001745.

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38

Luo, Shuang, Ziwei Hu, and Qiang Zhu. "Dearomative C–C and C–N bond cleavage of 2-arylindoles: transition-metal-free access to 2-aminoarylphenones." Organic Chemistry Frontiers 3, no. 3 (2016): 364–67. http://dx.doi.org/10.1039/c5qo00394f.

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A transition-metal-free conversion of 2-arylindoles to 2-aminoarylphenones, using environmentally benign O<sub>2</sub> as the sole oxidant, has been developed. This novel oxidative dearomatization process involves cleavage of two C–C and one C–N bonds followed by new C–C and C–O bond formation.
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39

Liu, Yuxia, Dong Xue, Chao Wang, and Linjuan Huang. "Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes." Synlett 31, no. 16 (2020): 1613–18. http://dx.doi.org/10.1055/s-0040-1707196.

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A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.
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40

Arcadi, Antonio, Emanuela Pietropaolo, Antonello Alvino, and Véronique Michelet. "Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles." Beilstein Journal of Organic Chemistry 10 (February 20, 2014): 449–58. http://dx.doi.org/10.3762/bjoc.10.42.

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The scope and limitations of gold-catalyzed tandem cycloisomerization/fluorination reactions of unprotected 2-alkynylanilines to have access to 3,3-difluoro-2-aryl-3H-indoles and 3-fluoro-2-arylindoles are described. An unprecedented aminoauration/oxidation/fluorination cascade reaction of 2-alkynylanilines bearing a linear alkyl group on the terminal triple bond is reported.
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41

Chittimalla, Santhosh, Chennakesavulu Bandi, Vinod Gadi, and Siva Gunturu. "Facile Synthesis of 2-Arylindoles through Plancher-Type Rearrangement of 3-Alkyl-3-Arylindolenines." Synlett 28, no. 15 (2017): 1994–99. http://dx.doi.org/10.1055/s-0036-1588448.

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3-Alkylindoles on reaction with a cyclohexa-2,4-dien-1-one catalyzed by BF3·OEt2 gave the corresponding 3-alkyl-3-arylindolenines in high yields through a tandem Michael addition/aromatization sequence. In the presence of HCl, these indolenine derivatives underwent a facile Plancher-type C-3 to C-2 aryl rearrangement to deliver the corresponding 2-arylindoles.
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42

Yamashiro, Toshiki, Koji Yamada, Haruka Yoshida, Yutaro Tomisaka, Takahide Nishi, and Takumi Abe. "Silver-Mediated Intramolecular Friedel–Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b] indolines and 3-Arylindoles." Synlett 30, no. 20 (2019): 2247–52. http://dx.doi.org/10.1055/s-0039-1690734.

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We disclose a silver-mediated intramolecular Friedel–Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b]indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b]indolines can be readily transformed into other heterocyclic moieties.
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43

Gattu, Radhakrishna, Suchandra Bhattacharjee, Karuna Mahato та Abu T. Khan. "Electronic effect of substituents on anilines favors 1,4-addition totrans-β-nitrostyrenes: access toN-substituted 3-arylindoles and 3-arylindoles". Organic & Biomolecular Chemistry 16, № 20 (2018): 3760–70. http://dx.doi.org/10.1039/c8ob00736e.

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A simple and an efficient method for the regioselective synthesis ofN-alkyl/aryl/H 3-arylindole derivatives fromN-substituted anilines andtrans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C.
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44

Li, Xiaojiao, Liujie Zhao, Zisong Qi, and Xingwei Li. "Construction of Atropisomeric 3-Arylindoles via Enantioselective Cacchi Reaction." Organic Letters 23, no. 15 (2021): 5901–5. http://dx.doi.org/10.1021/acs.orglett.1c02012.

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45

Golubeva, G. A., M. K. Ostrovskii, V. G. Zabrodnyaya, and Yu N. Portnov. "Synthesis and structure of substituted 2-amino-3-arylindoles." Chemistry of Heterocyclic Compounds 21, no. 8 (1985): 896–901. http://dx.doi.org/10.1007/bf00519818.

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46

Murru, Siva, August A. Gallo, and Radhey S. Srivastava. "ChemInform Abstract: Copper-Catalyzed Direct Synthesis of 3-Arylindoles." ChemInform 42, no. 34 (2011): no. http://dx.doi.org/10.1002/chin.201134109.

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47

Wang, Menglan, Yudong Li, Qing-An Wu, Shuping Luo, and Yuehui Li. "Iron-Promoted Construction of Indoles via Intramolecular Oxidative C–N Coupling of 2-Alkenylanilines Using Persulfate." Synthesis 51, no. 16 (2019): 3085–90. http://dx.doi.org/10.1055/s-0037-1611521.

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Indole scaffold synthesis relies primarily on oxidative C–H amination of N-protected alkenylanilines for C–N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K2S2O8 as oxidant in the presence of catalytic amounts of FeF2. The K2S2O8/FeF2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
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48

K., C. GUPTA, and MANGLUM P. "Synthesis of 2-Arylindoles via Aza-ring Closure of Sulphonium Salts." Journal of Indian Chemical Society Vol. 65, Mar 1988 (1988): 223–25. https://doi.org/10.5281/zenodo.6090178.

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Department of Chemistry, D. V. (P. G.) College, Orai-285 001 <em>Manuscript received 23 September 1987, revised 6 January 1988, accepted 13 January 1988</em> MANY routes have been devised to synthesise 2- arylindoles, but the methods are not versatile because the reactions involve drastic reaction conditions. Hirroze <em>et al.</em><sup>1</sup> reported the reaction of <em>N</em>-phenacylpyridinium bromide with anilines to furnish 2-phenylindoles. Junjappa<sup>2 </sup>extended this reaction using phenacyldimethylsulphonium bromide. Bansal <em>et al</em>. <sup>3,4</sup>&nbsp; reported the synth
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49

Pi, Chao, Yaping Qu, Xiuling Cui, and Yangjie Wu. "Silver-Catalyzed C—H Alkylation of 2-Arylindoles with Maleimides." Chinese Journal of Organic Chemistry 40, no. 3 (2020): 740. http://dx.doi.org/10.6023/cjoc201907040.

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Belley, Michel, Daniel Beaudoin, Petar Duspara, Effiette Sauer, Gabriel St-Pierre, and Laird Trimble. "Synthesis and Reactivity of N-Hydroxy-2-Amino-3-Arylindoles." Synlett 2007, no. 19 (2007): 2991–94. http://dx.doi.org/10.1055/s-2007-990969.

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