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Статті в журналах з теми "Aryne Chemistry"

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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

Brown, Roger F. C. "Flash Vacuum Pyrolytic Generation of Arynes - in Retrospect." Australian Journal of Chemistry 63, no. 7 (2010): 1002. http://dx.doi.org/10.1071/ch10086.

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Анотація:

The development of the chemistry of benzyne and of arynes under flash vacuum pyrolytic conditions was strongly influenced by a parallel study of the chemistry of propadienones, and by the discovery of the acetylene/methylenecarbene rearrangement. A limited range of typical aryne reactions studied at The Australian National University and at Monash University from 1965 to 1996 is described, and pathways of aryne formation are considered.

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2

Lee, Daesung, and Sourav Ghorai. "Aryne-Based Multicomponent Coupling Reactions." Synlett 31, no. 08 (March 20, 2020): 750–71. http://dx.doi.org/10.1055/s-0039-1690824.

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Анотація:

Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

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3

Idiris, Fahima I. M., and Christopher R. Jones. "Recent advances in fluoride-free aryne generation from arene precursors." Organic & Biomolecular Chemistry 15, no. 43 (2017): 9044–56. http://dx.doi.org/10.1039/c7ob01947e.

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Анотація:

Aryne chemistry has flourished in the past few decades. This review highlights new aryne precursors that operate under fluoride-free conditions as alternative methodologies to the popular fluoride-mediated ortho-silylaryl triflates.

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4

Martin, Nelson, and Ruchi Bharti. "Arynes in Natural Product Synthesis." International Journal for Research in Applied Science and Engineering Technology 11, no. 4 (April 30, 2023): 2633–44. http://dx.doi.org/10.22214/ijraset.2023.50703.

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Abstract: Arynes are a unique class of intermediates used in synthetic organic chemistry, and research interest has been intensely focused on their peculiar reactivities. Arynes have been researched for almost a century. However, difficulties in monitoring these reactive species, as well as difficulties in creating synthetically viable techniques for their synthesis and trapping, have restricted their application. A key tactic for achieving the racemic and enantiopure total synthesis of a broad variety of natural compounds or their structural derivatives. The chemistry of arynes has advanced significantly over the past thirty years, particularly in the field of transition metal carbon- carbon and carbon-heteroatom bond-forming mechanisms. The field’s fast growth is largely attributable to the development of mild aryne production processes. To create a natural product with complex organic molecules, the role of aryne intermediates was non-replaceable. These organic substances are often used in medicine, therapies, or as raw material for the synthesis of other substances. Moreover, they may perform important biological tasks. There are numerous methods for synthesizing natural compounds including total synthesis, semi-synthesis, and biosynthesis. Total synthesis is the process of creating natural products entirely chemically from basic precursors as well as it can be produced in large quantities and can reveal information about its biological activity. One of the developments in Arynes’ chemistry is the chemical rearrangements brought about by this electrophilic intermediate. It is not feasible to use conventional methods in a single step. This review article discusses how arynes are used to create natural products. Arynes has a wide range of functionality in the field of scientific research. The evolution of this method has made a tremendous change in the total synthesis of natural products. Benzynes enabled creative synthesis in mild conditions. The transformation has expanded to investigate various reaction classes such as nucleophilic addition, (4+2), and (2+2) cycloaddition strategies and metal-catalyzed reactions are shown and explained in this article. This review will provide an idea about how the arynes act as an intermediate in those reaction mechanisms and enlighten the scope of these aryne intermediate.

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5

Neog, Kashmiri, and Pranjal Gogoi. "Recent advances in the synthesis of organophosphorus compounds via Kobayashi's aryne precursor: a review." Organic & Biomolecular Chemistry 18, no. 47 (2020): 9549–61. http://dx.doi.org/10.1039/d0ob01988g.

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6

Ito, Motoki, Yuka Yamabayashi, Mio Oikawa, Emi Kano, Kazuhiro Higuchi, and Shigeo Sugiyama. "Silica gel-induced aryne generation from o-triazenylarylboronic acids as stable solid precursors." Organic Chemistry Frontiers 8, no. 12 (2021): 2963–69. http://dx.doi.org/10.1039/d1qo00385b.

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Анотація:

We developed o-triazenylarylboronic acids as stable solid aryne precursors, which generate arynes under mild conditions using silica gel as the sole reagent and undergo reactions with a range of arynophiles both in solution and in the solid-state.

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7

Tanaka, Hideya, Hitoshi Kuriki, Teruhiko Kubo, Itaru Osaka, and Hiroto Yoshida. "Copper-catalyzed arylstannylation of arynes in a sequence." Chemical Communications 55, no. 46 (2019): 6503–6. http://dx.doi.org/10.1039/c9cc02738f.

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Diverse ortho-stannylbiaryls and teraryls have been synthesized by copper-catalyzed arylstannylation of arynes, in which the single or dual insertion of arynes into arylstannanes is precisely controllable by simply changing the equivalence of the aryne precursors employed.

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8

Nakajima, Hana, Yuki Hazama, Yuki Sakata, Keisuke Uchida, Takamitsu Hosoya, and Suguru Yoshida. "Diverse diaryl sulfide synthesis through consecutive aryne reactions." Chemical Communications 57, no. 21 (2021): 2621–24. http://dx.doi.org/10.1039/d0cc08373a.

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9

Wenk, Hans Henning, Michael Winkler, and Wolfram Sander. "One Century of Aryne Chemistry." Angewandte Chemie International Edition 42, no. 5 (February 3, 2003): 502–28. http://dx.doi.org/10.1002/anie.200390151.

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10

Mhaske, Santosh, and Ranjeet Dhokale. "Transition-Metal-Catalyzed Reactions Involving Arynes." Synthesis 50, no. 01 (November 22, 2017): 1–16. http://dx.doi.org/10.1055/s-0036-1589517.

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Анотація:

The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.1 Introduction2 Insertion of Arynes3 Annulation of Arynes4 Cycloaddition of Arynes5 Multicomponent Reactions of Arynes6 Miscellaneous Reactions of Arynes7 Total Synthesis of Natural Products Using Arynes8 Conclusion

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11

Sureshbabu, Popuri, Vinod Bhajammanavar, Venkata Surya Kumar Choutipalli, Venkatesan Subramanian, and Mahiuddin Baidya. "Unorthodox cascade reaction of arynes and N-nitrosamides leading to indazole scaffolds." Chemical Communications 58, no. 8 (2022): 1187–90. http://dx.doi.org/10.1039/d1cc05655g.

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A cascade annulation of arynes with N-alkyl-N-nitrosamides is developed by leveraging aryne σ-insertion and C(sp3)–H bond functionalization strategies under transition-metal-free conditions to access indazoles in high yields and regioselectivity.

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12

Sharma, Abhilash, and Pranjal Gogoi. "Transition-metal free C(sp2)–C(sp2) bond formation: arylation of 4-aminocoumarins using arynes as an aryl source." Organic & Biomolecular Chemistry 17, no. 40 (2019): 9014–25. http://dx.doi.org/10.1039/c9ob01919g.

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Анотація:

A mild, efficient and transition-metal free synthetic strategy has been developed for the α-arylation of 4-aminocoumarins using arynes as an aryl source. This synthetic strategy proceeds via C(sp²)–C(sp²) bond formation between 4-aminocoumarins and aryne precursors in a single step in the absence of a metal-catalyst.

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13

Li, Yang, Dachuan Qiu, and Jiarong Shi. "Domino Aryne Precursor: A Step beyond the Boundary of Traditional Aryne Chemistry." Synlett 26, no. 16 (July 9, 2015): 2194–98. http://dx.doi.org/10.1055/s-0034-1381041.

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14

Uchida, Keisuke, Suguru Yoshida, and Takamitsu Hosoya. "Synthetic Aryne Chemistry toward Multicomponent Coupling." Journal of Synthetic Organic Chemistry, Japan 77, no. 2 (February 1, 2019): 145–62. http://dx.doi.org/10.5059/yukigoseikyokaishi.77.145.

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15

Cambie, RC, PI Higgs, PS Rutledge, and PD Woodgate. "Aryne Chemistry of Podocarpic Acid Derivatives." Australian Journal of Chemistry 47, no. 8 (1994): 1483. http://dx.doi.org/10.1071/ch9941483.

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Анотація:

The anthranilic acid (2), a key intermediate for the generation of an aryne at C13 of podocarpic acid derivatives, was synthesized from the 14-amino compound (5) which in turn was generated regiospecifically in high yield by treatment of the 13-bromo compound (25) with sodamide in liquid ammonia. The amine was converted into the anthranilic acid by two separate routes: firstly by directed lithiation and trapping of the lithium species with a CO2 moiety, and secondly by oxidative cleavage of an isatin fused across positions 13 and 14.

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16

Suh, Sung-Eun, Shuming Chen, K. N. Houk, and David M. Chenoweth. "The mechanism of the triple aryne–tetrazine reaction cascade: theory and experiment." Chemical Science 9, no. 39 (2018): 7688–93. http://dx.doi.org/10.1039/c8sc01796d.

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This article describes an experimental and computational investigation on the possible aryne reactivity modes in the course of the reaction of two highly energetic molecules, an aryne and a 1,2,4,5-tetrazine.

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17

Qiu, Dachuan, Jiarong Shi, and Yang Li. "ChemInform Abstract: Domino Aryne Precursor: A Step Beyond the Boundary of Traditional Aryne Chemistry." ChemInform 47, no. 7 (January 2016): no. http://dx.doi.org/10.1002/chin.201607155.

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18

Mesgar, Milad, Justin Nguyen-Le, and Olafs Daugulis. "1,2-Bis(arylthio)arene synthesis via aryne intermediates." Chemical Communications 55, no. 64 (2019): 9467–70. http://dx.doi.org/10.1039/c9cc03863a.

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19

Li, Pan, Chunrui Wu, Jingjing Zhao, Yang Li, Weichao Xue, and Feng Shi. "One-pot synthesis of dihydrobenzisoxazoles from hydroxylamines, acetylenedicarboxylates, and arynes via in situ generation of nitrones." Canadian Journal of Chemistry 91, no. 1 (January 2013): 43–50. http://dx.doi.org/10.1139/cjc-2012-0199.

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Анотація:

Aryne [3 + 2] cycloaddition with nitrones generated in situ from the addition of hydroxylamines to acetylenedicarboxylates affords moderate to good yields of dihydrobenzisoxazoles. This reaction extends the current scope of aryne cycloaddition to include in situ generated nitrones and produces functionalized dihydrobenzisoxazoles with a quaternary center.

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20

Xie, Chunsong, Leifang Liu, Yuhong Zhang, and Peixin Xu. "Copper-Catalyzed Alkyne−Aryne and Alkyne−Alkene−Aryne Coupling Reactions." Organic Letters 10, no. 12 (June 2008): 2393–96. http://dx.doi.org/10.1021/ol800651h.

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21

CAMBIE, R. C., P. I. HIGGS, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Aryne Chemistry of Podocarpic Acid Derivatives." ChemInform 25, no. 52 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199452212.

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22

Lin, Yibei, Yali Chen, Xuyan Ma, Di Xu, Weiguo Cao, and Jie Chen. "Aryne click chemistry: synthesis of oxadisilole fused benzotriazoles or naphthotriazoles from arynes and azides." Tetrahedron 67, no. 5 (February 2011): 856–59. http://dx.doi.org/10.1016/j.tet.2010.12.039.

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23

Zilla, Mahesh K., Sheena Mahajan, Rajni Khajuria, Vivek K. Gupta, Kamal K. Kapoor, and Asif Ali. "An efficient synthesis of 4-phenoxy-quinazoline, 2-phenoxy-quinoxaline, and 2-phenoxy-pyridine derivatives using aryne chemistry." RSC Advances 11, no. 6 (2021): 3477–83. http://dx.doi.org/10.1039/d0ra09994e.

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24

Shi, Jiarong, Yuanyuan Li, and Yang Li. "Aryne multifunctionalization with benzdiyne and benztriyne equivalents." Chemical Society Reviews 46, no. 6 (2017): 1707–19. http://dx.doi.org/10.1039/c6cs00694a.

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25

Hu, Jinbo, and Yuwen Zeng. "Bridging Fluorine and Aryne Chemistry: Vicinal Difunctionalization of Arynes Involving Nucleophilic Fluorination, Trifluoromethylation, or Trifluoromethylthiolation." Synthesis 48, no. 14 (May 24, 2016): 2137–50. http://dx.doi.org/10.1055/s-0035-1561641.

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26

Hu, Jinbo, and Yuwen Zeng. "Bridging Fluorine and Aryne Chemistry: Vicinal Difunctionalization of Arynes Involving Nucleophilic Fluorination, Trifluoromethylation, or Trifluoromethylthiolation." Synthesis 48, no. 14 (July 4, 2016): e3-e3. http://dx.doi.org/10.1055/s-0035-1562547.

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27

Su, Shikuan, Jianxiong Li, Mingming Sun, Hongbin Zhao, Yali Chen, and Jian Li. "A domino reaction of 2-isocyanophenyloxyacrylate and aryne to synthesize arenes with vicinal olefin and benzoxazole." Chemical Communications 54, no. 69 (2018): 9611–14. http://dx.doi.org/10.1039/c8cc05735d.

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An unusual domino reaction of 2-isocyanophenyloxyacrylate and aryne has been disclosed. The present strategy experiences nucleophilic addition, Michael addition, carbon–oxygen cleavage, and cyclization, thus enabling the quick aryne vicinal difunctionalization by the installation of a benzoxazole and an olefin.

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28

Yoshida, Suguru, and Takamitsu Hosoya. "The Renaissance and Bright Future of Synthetic Aryne Chemistry." Chemistry Letters 44, no. 11 (November 5, 2015): 1450–60. http://dx.doi.org/10.1246/cl.150839.

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29

Bennett, Martin A. "Aryne Complexes of Zerovalent Metals of the Nickel Triad." Australian Journal of Chemistry 63, no. 7 (2010): 1066. http://dx.doi.org/10.1071/ch10198.

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Анотація:

The chemistry of dihapto-aryne complexes of the zerovalent Group 10 metals of general formula [M(η2-aryne)L2] (M = Ni, Pd, Pt; L = various tertiary phosphines) is reviewed, with emphasis on the highly reactive nickel(0) compounds (aryne = benzyne, C6H4; 4,5-difluorobenzyne, 4,5-C6H2F2; 2,3-naphthalyne, 2,3-C10H6; L2 = 2 PEt3, 2 PiPr3, 2 PCy3, dcpe). These can be generated by alkali metal reduction of the appropriate (2-halogenoaryl)nickel(ii) halide precursors, such as [NiX(2-XC6H4)L2], which in turn are accessible by oxidative addition of the 1,2-dihaloarene to nickel(0) precursors such as [Ni(1,5-COD)2]. The X-ray structure of [Ni(η2-C6H4)(dcpe)] shows that this compound is a typical 16-electron Ni(0) (3d10) species in which benzyne acts as a 2π-electron donor. Several unusual organonickel compounds derived from [Ni(η2-4,5-C6H2F2)(PEt3)2] have been isolated recently, including [Ni2(μ-η2:η2-4,5-C6H2F2)(PEt3)4], in which a 4π-electron donor 4,5-difluorobenzyne is located at right-angles to a pair of nickel atoms. Free benzyne can be intercepted by both [Ni(η2-C2H4)(dcpe)] and [Pt(η2-C2H4)(PPh3)2], but the resulting benzyne complexes rapidly insert benzyne to give the appropriate η1:η1-2,2′-biphenylyl complexes. [Pt(η2-C6H4)(PPh3)2] also undergoes rapid ortho-metallation to give [PtPh(2-C6H4PPh2)(PPh3)]. However, a trapping reaction has been used to make the first 1,4-benzdiyne complex, [{Ni(dcpe)2}2(μ-η2:η2-1,4-C6H2)] by treatment of the 4-fluorobenzyne complex [Ni(η2-4-FC6H3)(dcpe)] with LiTMP. The use of alkali metals in the preparation of the η2-benzyne complexes is avoided in a more recently developed procedure, which starts from (2-bromophenyl)boronic acid, and is based on Suzuki–Miyaura coupling. This procedure has made accessible for the first time an aryne complex of palladium(0), [Pd(η2-C6H4)(PCy3)2], and the labile nickel(0) complex [Ni(η2-C6H4)(PPh3)2]. The aryne-nickel(0) complexes Ni(η2-aryne)L2 (L2 = 2 PEt3, dcpe) undergo sequential insertions into the aryne-metal bond with unsaturated molecules, such as CO, C2F4, substituted alkynes, substituted diynes, alkynylphosphines, and alkynyl thioethers, often with considerable regioselectivity. After the reductive elimination of two nickel-carbon σ-bonds, a variety of interesting polycyclic compounds can be obtained.

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30

Gupta, Saswata, Yongjia Lin, Yuanzhi Xia, Donald J. Wink, and Daesung Lee. "Alder-ene reactions driven by high steric strain and bond angle distortion to form benzocyclobutenes." Chemical Science 10, no. 7 (2019): 2212–17. http://dx.doi.org/10.1039/c8sc04277b.

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31

Matsuzawa, Tsubasa, Takamitsu Hosoya, and Suguru Yoshida. "One-step synthesis of benzo[b]thiophenes by aryne reaction with alkynyl sulfides." Chemical Science 11, no. 35 (2020): 9691–96. http://dx.doi.org/10.1039/d0sc04450d.

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32

Crump, Stephen L., Jill Netka, and Bruce Rickborn. "Preparation of isobenzofuran-aryne cycloadducts." Journal of Organic Chemistry 50, no. 15 (July 1985): 2746–50. http://dx.doi.org/10.1021/jo00215a031.

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33

Pollart, Daniel J., and Bruce Rickborn. "Regioselectivity of alkoxyisobenzofuran-aryne cycloadditions." Journal of Organic Chemistry 52, no. 5 (March 1987): 792–98. http://dx.doi.org/10.1021/jo00381a016.

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34

Lin, Yibei, Yali Chen, Xuyan Ma, Di Xu, Weiguo Cao, and Jie Chen. "ChemInform Abstract: Aryne Click Chemistry: Synthesis of Oxadisilole Fused Benzotriazoles or Naphthotriazoles from Arynes and Azides." ChemInform 42, no. 27 (June 9, 2011): no. http://dx.doi.org/10.1002/chin.201127025.

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35

Jones, Christopher, Weitao Sun, Piera Trinchera, Nada Kurdi, David Palomas, Rachel Crespo-Otero, Saeed Afshinjavid, and Farideh Javid. "Aryne-Mediated Arylation of Hantzsch Esters: Access to Highly Substituted Aryl-dihydropyridines, Aryl-tetrahydropyridines and Spiro[benzocyclobutene-1,1′-(3′,4′-dihydropyridines)]." Synthesis 50, no. 23 (October 25, 2018): 4591–605. http://dx.doi.org/10.1055/s-0037-1611065.

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Анотація:

This is a full account of our studies into the generation of highly functionalised 2-aryl-1,2-dihydropyridines and 2-methylene-3-aryl-1,2,3,4-tetrahydropyridines via intermolecular aryne ene reactions of Hantzsch esters. Furthermore, exposure to excess aryne revealed unusual 3′-aryl-spiro[benzocyclobutene-1,1′-(3′,4′-dihydropyridines)]. Mechanistic insights are provided by deuterium-labelling studies and DFT calculations, whilst preliminary cytotoxicity investigations reveal that the spirocycles are selective against colon carcinomas over ovarian cancer cell lines and that all the compounds have high selectivity indices with regards to non-cancer cells.

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36

Roy, Tony, Manikandan Thangaraj, Trinadh Kaicharla, Rupa V. Kamath, Rajesh G. Gonnade, and Akkattu T. Biju. "The Aryne [2,3] Stevens Rearrangement." Organic Letters 18, no. 20 (October 13, 2016): 5428–31. http://dx.doi.org/10.1021/acs.orglett.6b02809.

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37

Li, Bingnan, Shaoyu Mai, and Qiuling Song. "Synthesis of fused benzimidazoles via successive nucleophilic additions of benzimidazole derivatives to arynes under transition metal-free conditions." Organic Chemistry Frontiers 5, no. 10 (2018): 1639–42. http://dx.doi.org/10.1039/c8qo00251g.

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38

Sanz, Roberto. "RECENT APPLICATIONS OF ARYNE CHEMISTRY TO ORGANIC SYNTHESIS. A REVIEW." Organic Preparations and Procedures International 40, no. 3 (June 2008): 215–91. http://dx.doi.org/10.1080/00304940809458089.

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39

Wu, Chunrui, and Feng Shi. "A Closer Look at Aryne Chemistry: Details that Remain Mysterious." Asian Journal of Organic Chemistry 2, no. 2 (January 17, 2013): 116–25. http://dx.doi.org/10.1002/ajoc.201200142.

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40

Tan, Jiajing, Binbin Liu, and Shuaisong Su. "Aryne triggered dearomatization reaction of isoquinolines and quinolines with chloroform." Organic Chemistry Frontiers 5, no. 21 (2018): 3093–97. http://dx.doi.org/10.1039/c8qo00838h.

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41

Neog, Kashmiri, Dhiraj Dutta, Babulal Das, and Pranjal Gogoi. "Aryne insertion into the PO bond: one-pot synthesis of quaternary phosphonium triflates." Organic & Biomolecular Chemistry 17, no. 26 (2019): 6450–60. http://dx.doi.org/10.1039/c9ob01157a.

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Rahman, Matiur, Avik Kumar Bagdi, Dmitry S. Kopchuk, Igor S. Kovalev, Grigory V. Zyryanov, Oleg N. Chupakhin, Adinath Majee, and Alakananda Hajra. "Recent advances in the synthesis of fluorinated compounds via an aryne intermediate." Organic & Biomolecular Chemistry 18, no. 47 (2020): 9562–82. http://dx.doi.org/10.1039/d0ob01638a.

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43

Pan, Xuan, Yantao Ma, and Zhanzhu Liu. "A concise synthesis of (E)-3-aryl-2,3,4,5-tetrahydro-1H-3-benzazonines by aryne induced [2,3] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines." Organic & Biomolecular Chemistry 16, no. 40 (2018): 7393–99. http://dx.doi.org/10.1039/c8ob02099j.

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44

Hazarika, Hemanta, Kangkana Chutia, Babulal Das, and Pranjal Gogoi. "One-pot synthesis of 3-substituted-3-hydroxyindolin-2-ones: three component coupling of N-protected isatin, aryne precursor and 1,3-cyclodione under metal-free conditions." New Journal of Chemistry 46, no. 1 (2022): 86–96. http://dx.doi.org/10.1039/d1nj04295e.

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45

Meerakrishna, Ramakrishnan Suseela, Suresh Snoxma Smile, Mohanakumaran Athira, Venkata Surya Kumar Choutipalli, and Ponnusamy Shanmugam. "Diverse reactivity of isatin-based N,N′-cyclic azomethine imine dipoles with arynes: synthesis of 1′-methyl-2′-oxospiro [indene-1,3′-indolines] and 3-aryl-3-pyrazol-2-oxindoles." New Journal of Chemistry 44, no. 27 (2020): 11593–601. http://dx.doi.org/10.1039/d0nj01684e.

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Анотація:

Reaction of aryne with isatin based N,N′-cyclic AMI 1,3-dipole afforded 3,3-disubstituted oxindole while methyl substitution on the pyrrolidine ring of 1,3-dipole directed [3+2] cycloaddition products.

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46

Venkatesh, Telugu, Prathama S. Mainkar, and Srivari Chandrasekhar. "Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion." Organic & Biomolecular Chemistry 17, no. 8 (2019): 2192–98. http://dx.doi.org/10.1039/c8ob03123a.

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47

Pavlyuk, D. E., S. Gundala, I. S. Kovalev, D. S. Kopchuk, A. P. Krinochkin, A. V. Budeev, G. V. Zyryanov, P. Venkatapuram, V. L. Rusinov, and O. N. Chupakhin. "Reactions of Perylene with Aryne Intermediates." Russian Journal of Organic Chemistry 55, no. 3 (March 2019): 409–11. http://dx.doi.org/10.1134/s1070428019030278.

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Payili, Nagaraju, Santhosh Reddy Rekula, Anjaiah Aitha, V. V. S. R. N. Anji Karun Mutha, Challa Gangu Naidu, and Satyanarayana Yennam. "Synthesis of dibenzo[a,d]cycloheptanoids via aryne insertion into 2-arylidene-1,3-indandiones." Organic & Biomolecular Chemistry 17, no. 43 (2019): 9442–46. http://dx.doi.org/10.1039/c9ob01900f.

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Hazarika, Hemanta, and Pranjal Gogoi. "Direct synthesis of ortho-methylthio allyl and vinyl ethers via three component reaction of aryne, activated alkene and DMSO." Organic & Biomolecular Chemistry 18, no. 14 (2020): 2727–38. http://dx.doi.org/10.1039/d0ob00275e.

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50

Winkler, Michael, and Wolfram Sander. "Matrix Isolation and Electronic Structure of Di- and Tridehydrobenzenes." Australian Journal of Chemistry 63, no. 7 (2010): 1013. http://dx.doi.org/10.1071/ch10113.

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Within the past four decades, matrix isolation spectroscopy has emerged as the method of choice for obtaining direct structural information on benzynes and related dehydroaromatics. In combination with quantum chemical computations, detailed insight into the structure and reactivity of di-, tri-, and tetradehydrobenzenes has been obtained. This Review focuses on rather recent developments in aryne chemistry with a special emphasis on the matrix isolation of tridehydrobenzenes and related systems.

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