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Journal articles on the topic 'Cyclophanes – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Rajakumar, Perumal, and Ramar Padmanabhan. "Synthesis, Anti-Arthritic, and Anti-Inflammatory Activity of N-Tosyl aza Cyclophanes." Australian Journal of Chemistry 65, no. 2 (2012): 186. http://dx.doi.org/10.1071/ch11435.

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The synthesis of novel N-tosyl tetraaza cyclophanes and N-tosyl diaza cyclophane incorporating m-terphenyl as spacer units is described. Anti-arthritic activity was studied by inhibition of the protein denaturation method (bovine serum albumin). All the N-tosyl aza cyclophanes exhibit excellent anti-arthritic activity. Anti-inflammatory activity of the synthesized cyclophanes was investigated using the human red blood cells (HRBC) membrane stabilization method and some of the N-tosyl aza cyclophanes exhibited good anti-inflammatory activity.

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2

Patel, Suraj, Tyson N. Dais, Paul G. Plieger, and Gareth J. Rowlands. "Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes." Beilstein Journal of Organic Chemistry 17 (June 29, 2021): 1518–26. http://dx.doi.org/10.3762/bjoc.17.109.

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Substituted [2.2]metaparacyclophanes are amongst the least studied of the simple cyclophanes. This is undoubtedly the result of the lengthy syntheses of these compounds. We report the simple synthesis of a rare example of a non-symmetric [2.2]metaparacyclophane. Treatment of [2.2]paracyclophane under standard nitration conditions gives a mixture of 4-nitro[2.2]paracyclophane, 4-hydroxy-5-nitro[2.2]metaparacyclophane and a cyclohexadienone cyclophane.

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3

Padnya, Pavel, Vladimir Gorbachuk, and Ivan Stoikov. "The Role of Calix[n]arenes and Pillar[n]arenes in the Design of Silver Nanoparticles: Self-Assembly and Application." International Journal of Molecular Sciences 21, no. 4 (2020): 1425. http://dx.doi.org/10.3390/ijms21041425.

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Silver nanoparticles (AgNPs) are an attractive alternative to plasmonic gold nanoparticles. The relative cheapness and redox stability determine the growing interest of researchers in obtaining selective plasmonic and electrochemical (bio)sensors based on silver nanoparticles. The controlled synthesis of metal nanoparticles of a defined morphology is a nontrivial task, important for such fields as biochemistry, catalysis, biosensors and microelectronics. Cyclophanes are well known for their great receptor properties and are of particular interest in the creation of metal nanoparticles due to a variety of cyclophane 3D structures and unique redox abilities. Silver ion-based supramolecular assemblies are attractive due to the possibility of reduction by “soft” reducing agents as well as being accessible precursors for silver nanoparticles of predefined morphology, which are promising for implementation in plasmonic sensors. For this purpose, the chemistry of cyclophanes offers a whole arsenal of approaches: exocyclic ion coordination, association, stabilization of the growth centers of metal nanoparticles, as well as in reduction of silver ions. Thus, this review presents the recent advances in the synthesis and stabilization of Ag (0) nanoparticles based on self-assembly of associates with Ag (I) ions with the participation of bulk platforms of cyclophanes (resorcin[4]arenes, (thia)calix[n]arenes, pillar[n]arenes).

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4

Okada, Yukihiro, Kenji Sugiyama, Masaki Kurahayashi, and Jun Nishimura. "Synthesis of three-bridged cyclophanes via meta- and ortho-cyclophane." Tetrahedron Letters 32, no. 21 (1991): 2367–70. http://dx.doi.org/10.1016/s0040-4039(00)79925-4.

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5

Rajakumar, Perumal, Ramar Padmanabhan, Chandrasekaran Ramprasath, Narayanasamy Mathivanan, Vaidhyanathan Silambarasan, and Devadasan Velmurugan. "Synthesis, Antimicrobial Activity, and Molecular Docking Study of Some Novel Cyclophanes with Imino Intra-Annular Functionality." Australian Journal of Chemistry 66, no. 1 (2013): 84. http://dx.doi.org/10.1071/ch12326.

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The synthesis and structural characterisation of novel imino cyclophanes incorporating various spacer units is described. All the imino cyclophanes exhibit comparable antibacterial activity against Gram positive (Bacillus subtillus, Staphylococcus aureus) and Gram negative (Escherchia coli, Klebsiella pneumonia) bacterial strains. The imino cyclophanes also exhibit good antifungal activity against human pathogenic fungus, Candida albicans.

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6

Kane, Vinayak V., Willem H. De Wolf, and Friedrich Bickelhaupt. "Synthesis of small cyclophanes." Tetrahedron 50, no. 16 (1994): 4575–622. http://dx.doi.org/10.1016/s0040-4020(01)85002-x.

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7

Meier, Herbert, and Klaus Müller. "Synthesis of Belt Cyclophanes." Angewandte Chemie International Edition in English 34, no. 1314 (1995): 1437–39. http://dx.doi.org/10.1002/anie.199514371.

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8

Barnes, Jonathan C., Michal Juríček, Nicolaas A. Vermeulen, Edward J. Dale, and J. Fraser Stoddart. "Synthesis of ExnBox Cyclophanes." Journal of Organic Chemistry 78, no. 23 (2013): 11962–69. http://dx.doi.org/10.1021/jo401993n.

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9

SHINMYOZU, T., M. HIRAKIDA, S. KUSUMOTO, M. TOMONOU, T. INAZU, and J. M. RUDZINSKI. "ChemInform Abstract: Multibridged (3n)Cyclophanes. Part 2. Synthesis of (35)(1,2,3,4,5) Cyclophane." ChemInform 25, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199437072.

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10

Filler, Robert, Garry L. Cantrell, Donald Wolanin, and Saiyid M. Naqvi. "Synthesis of polyfluoroaryl [2.2] cyclophanes." Journal of Fluorine Chemistry 30, no. 4 (1986): 399–414. http://dx.doi.org/10.1016/s0022-1139(00)85095-2.

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11

Jiang, Zhong-Ling, Jia-Ming Yan, Cheng Yang, De-Qi Yuan †, and Ru-Gang Xie. "Synthesis of Novel Squarylium Cyclophanes." Synthetic Communications 28, no. 1 (1998): 119–22. http://dx.doi.org/10.1080/00397919808005080.

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12

Rajakumar, Perumal, Muthialu Srisailas, and Rajagopal Kanagalatha. "Synthesis of annularly functionalized cyclophanes." Tetrahedron 59, no. 28 (2003): 5365–71. http://dx.doi.org/10.1016/s0040-4020(03)00685-9.

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13

Ried, W., and S. Aboul-Fetouh. "Synthesis of substituted heterocyclic cyclophanes." Tetrahedron 44, no. 11 (1988): 3399–404. http://dx.doi.org/10.1016/s0040-4020(01)85975-5.

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14

Shinmyozu, Teruo, Shirou Kusumoto, Sachiyo Nomura, Haruo Kawase, and Takahiko Inazu. "Multibridged [3n]Cyclophanes, 1. Synthesis of [34](1,2,3,5)- and -(1,2,4,5)Cyclophanes." Chemische Berichte 126, no. 8 (1993): 1815–18. http://dx.doi.org/10.1002/cber.19931260810.

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15

Liu, Zhichang, Chenghe Zhou, Xiaoyu Su, and Rugang Xie. "First synthesis of Estrogen-Imidazolium Cyclophanes." Synthetic Communications 29, no. 17 (1999): 2979–83. http://dx.doi.org/10.1080/00397919908086472.

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16

Kohmoto, Shigeo, Daisuke Fukui, Takushi Nagashima, Keiki Kishikawa, Makoto Yamamoto, and Kazutoshi Yamada. "Synthesis of steroidal triply-bridged cyclophanes." Chemical Communications, no. 16 (1996): 1869. http://dx.doi.org/10.1039/cc9960001869.

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17

KANE, V. V., W. H. DE WOLF, and F. BICKELHAUPT. "ChemInform Abstract: Synthesis of Small Cyclophanes." ChemInform 25, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199433303.

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18

Tobe, Y., and T. Takeda. "ChemInform Abstract: Synthesis of Polynuclear Cyclophanes." ChemInform 43, no. 28 (2012): no. http://dx.doi.org/10.1002/chin.201228238.

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19

Garcia, Maurie E., Julia A. Gavin, Nanlin Deng, Andrei A. Andrievsky, and Thomas E. Mallouk. "Combinatorial synthesis of modular chiral cyclophanes." Tetrahedron Letters 37, no. 46 (1996): 8313–16. http://dx.doi.org/10.1016/0040-4039(96)01945-4.

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20

Hayashida, Osamu, and Yu Kaku. "Synthesis of Dabsyl-Appended Cyclophanes and Their Heterodimer Formation with Pyrene-Appended Cyclophanes." Journal of Organic Chemistry 78, no. 20 (2013): 10437–42. http://dx.doi.org/10.1021/jo4018843.

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21

Ghasemabadi, Parisa Ghods, Tieguang Yao, and Graham J. Bodwell. "Cyclophanes containing large polycyclic aromatic hydrocarbons." Chemical Society Reviews 44, no. 18 (2015): 6494–518. http://dx.doi.org/10.1039/c5cs00274e.

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Big, bigger, biggest. This Review puts the spotlight on the handful of PAHs with four or more rings that have been incorporated into cyclophanes. Lessons in synthesis, structure, fundamental concepts and properties abound in these remarkable molecules that feature PAHs ranging in size from pyrene to hexabenzocoronene.

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22

Kannan, Arunachalam, Henning Hopf, Ina Dix, Peter G. Jones, and Ludger Ernst. "Synthesis, structure, and first reactions of a new class of thiacyclophanes." Canadian Journal of Chemistry 95, no. 3 (2017): 278–85. http://dx.doi.org/10.1139/cjc-2016-0358.

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In our effort to prepare [m.n]cyclophanes carrying functional groups in their molecular bridges, the thiacyclophanes 14, 19, 20, and 21 have been prepared by simple routes from the pseudo-gem dibromide 10a and the corresponding bis-thiol 10b. The triply-bridged bis-thia-cyclophanes 14, and 19-21 were characterized by their spectroscopic data as well as by X-ray structural analyses. The meta-isomer 20 was oxidized to the bis-sulfone 23, which on flash vacuum pyrolysis (FVP) yielded a product mixture presumably containing the hydrocarbon 26 with a cleaved molecular bridge. Subjecting 23 to Ramberg-Bäcklund conditions (CCl4, NaOH, phase transfer catalysis) provided the chloride 24 in poor yield (9%), a [2.2]paracyclophane in which the new molecular bridge is fully conjugated.

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23

Okamoto, Hideki, Hiroyuki Takemura, and Kyosuke Satake. "A Convenient Synthesis of Trifluoroacetamide Derivatives of Diaza[32]cyclophanes and Triaza[33]cyclophanes." Synthesis 2008, no. 1 (2008): 39–44. http://dx.doi.org/10.1055/s-2007-1000825.

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24

Otte, Matthias, Martin Lutz, and Robertus J. M. Klein Gebbink. "Selective Synthesis of Hetero-Sequenced Aza-Cyclophanes." European Journal of Organic Chemistry 2017, no. 12 (2017): 1657–61. http://dx.doi.org/10.1002/ejoc.201700106.

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25

Heuft, Matthew A., and Alex G. Fallis. "Template-Directed Synthesis of Helical Phenanthroline Cyclophanes." Angewandte Chemie International Edition 41, no. 23 (2002): 4520–23. http://dx.doi.org/10.1002/1521-3773(20021202)41:23<4520::aid-anie4520>3.0.co;2-j.

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26

JIANG, Z. L., J. M. YAN, C. YAN, D. Q. YUAN, and R. G. XIE. "ChemInform Abstract: Synthesis of Novel Squarylium Cyclophanes." ChemInform 29, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199820210.

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27

Bodwell, Graham J., and Penchal Reddy Nandaluru. "Olefination Reactions in the Synthesis of Cyclophanes." Israel Journal of Chemistry 52, no. 1-2 (2012): 105–38. http://dx.doi.org/10.1002/ijch.201200003.

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28

Zhou, Cheng-He, Ru-Gang Xie, and Hua-Ming Zhao. "CONVENIENT AND EFFICIENT SYNTHESIS OF IMIDAZOLIUM CYCLOPHANES." Organic Preparations and Procedures International 28, no. 3 (1996): 345–47. http://dx.doi.org/10.1080/00304949609356541.

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29

Tanaka, Ken. "Catalytic Enantioselective Synthesis of Planar Chiral Cyclophanes." Bulletin of the Chemical Society of Japan 91, no. 2 (2018): 187–94. http://dx.doi.org/10.1246/bcsj.20170346.

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30

Gibson (née Thomas), Susan E., Jerome O. Jones, S. Barret Kalindjian, Jamie D. Knight, Jonathan W. Steed, and Matthew J. Tozer. "Synthesis and structural analysis of dehydrophenylalanine cyclophanes." Chem. Commun., no. 17 (2002): 1938–39. http://dx.doi.org/10.1039/b205752m.

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31

Rajakumar, Perumal, and Merikapudi Gayatri Swaroop. "Synthesis of novel indole based cyclophanes and cylindrical cyclophanes by tandem alkylation methodology using NaH." Tetrahedron Letters 47, no. 18 (2006): 3019–22. http://dx.doi.org/10.1016/j.tetlet.2006.03.013.

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32

Wang, Huan, Alexander V. Predeus, and William D. Wulff. "Synthesis of [m.n]Cyclophanes: Regiochemistry Transfer from Vinyl Halides to Cyclophanes via Fischer Carbene Complexes." Chemistry - A European Journal 19, no. 25 (2013): 8261–67. http://dx.doi.org/10.1002/chem.201204434.

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33

Sargent, Melvyn V., and Sirichai Wangchareontrakul. "Synthesis of the cyclophane tetramethoxyturriane: a derivative of the phenolic cyclophanes of Grevillea striata R. Br." Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1990): 129. http://dx.doi.org/10.1039/p19900000129.

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34

Hou, Xiaomeng, Linfei Xu, Xuesong Tang, Yang Song, and Yinjuan Bai. "Synthesis and Crystal Structure of Novel Benzimidazole Cyclophanes." Chinese Journal of Organic Chemistry 33, no. 3 (2013): 643. http://dx.doi.org/10.6023/cjoc201209043.

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35

Srisailas, Muthialu, and Perumal Rajakumar. "Synthesis of annularly functionalised BINOL-based chiral cyclophanes." Journal of Chemical Research 2006, no. 10 (2006): 671–74. http://dx.doi.org/10.3184/030823406779173677.

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36

Liu, Xiao, Yudao Ma, Wenzeng Duan, Fuyan He, Lei Zhao, and Chun Song. "Synthesis of Cyclophanes with Planar and Helical Chirality." Journal of Organic Chemistry 76, no. 6 (2011): 1953–56. http://dx.doi.org/10.1021/jo102538y.

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37

Yuan, Yi, Ge Gao, Zong-Lin Jiang, et al. "Synthesis and selective anion recognition of imidazolium cyclophanes." Tetrahedron 58, no. 44 (2002): 8993–99. http://dx.doi.org/10.1016/s0040-4020(02)01153-5.

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38

Consiglio, Giuseppe A., Salvatore Failla, and Paolo Finocchiaro. "Synthesis and characterization of conformationally flexible phosphonated cyclophanes." Mendeleev Communications 9, no. 3 (1999): 90–91. http://dx.doi.org/10.1070/mc1999v009n03abeh001109.

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39

Sudhakar, Sundarraj, Jui-Hung Hsu, Yi-Hung Liu, et al. "Synthesis and photophysical studies of siloxane-tethered cyclophanes." Silicon Chemistry 1, no. 5/6 (2002): 403–7. http://dx.doi.org/10.1023/b:silc.0000025611.53436.e0.

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40

Takemura, Hiroyuki, K� Takehara, and Masafumi Ata. "Synthesis and Redox Behavior of Wurster Blue Cyclophanes." European Journal of Organic Chemistry 2004, no. 23 (2004): 4936–41. http://dx.doi.org/10.1002/ejoc.200400289.

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41

KOHMOTO, S., D. FUKUI, T. NAGASHIMA, K. KISHIKAWA, M. YAMAMOTO, and K. YAMADA. "ChemInform Abstract: Synthesis of Steroidal Triply-Bridged Cyclophanes." ChemInform 27, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199648086.

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42

Liu, Zhichang, Chenghe Zhou, Xiaoyu Su, and Rugang Xie. "ChemInform Abstract: First Synthesis of Estrogen-Imidazolium Cyclophanes." ChemInform 30, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199943183.

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43

Xu, Xiao-Wei, Xin-Long Wang, Ai-Ming Wu, Zhi-Ming Zheng, Mei-Gui Yi, and Rong Xiao. "Synthesis and molecular recognition of novel multiimidazole cyclophanes." Journal of Heterocyclic Chemistry 46, no. 6 (2009): 1137–41. http://dx.doi.org/10.1002/jhet.188.

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44

Park, Kwanghee Koh, In Kyu Han, and Joon Woo Park. "Photochemical Synthesis of Cyclophanes Containing Tethered Benzofuran Rings." Journal of Organic Chemistry 66, no. 20 (2001): 6800–6802. http://dx.doi.org/10.1021/jo0103165.

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45

Yu, DingYi, Tai Peng, Iqbal Javad, HongYu Zhang, JingYing Zhang, and Yue Wang. "Dimeric quinacridone cyclophanes: Synthesis, structures, and photophysical properties." Science China Chemistry 54, no. 2 (2011): 314–19. http://dx.doi.org/10.1007/s11426-010-4194-6.

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46

Tsuge, Akihiko, Takahiro Okamoto, and Tetsuji Moriguch. "Structure and Conformational Properties of three-layered Cyclophanes prepared by a one-pot Synthesis." Journal of Chemical Research 2007, no. 7 (2007): 429–31. http://dx.doi.org/10.3184/030823407x228786.

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The coupling reactions of substituted bis(bromomethyl)benzene components and tetra(mercaptomethyl)benzene derivatives have been carried out under heterogeneous dilute reaction conditions to afford the three-layered cyclophanes 3a–e as three kinds of conformational isomers in moderate yields.

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47

Kotha, Sambasivarao, Ajay Kumar Chinnam, and Mukesh Eknathrao Shirbhate. "Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps." Beilstein Journal of Organic Chemistry 11 (August 31, 2015): 1514–19. http://dx.doi.org/10.3762/bjoc.11.165.

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48

Tashiro, Masashi, Cristian Simion, Alina Simion, et al. "Synthesis of New Dihydroxy-dioxygenated ortho-[2,x]Cyclophanes." HETEROCYCLES 53, no. 11 (2000): 2459. http://dx.doi.org/10.3987/com-00-9022.

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49

Fox, Joseph M., Daniel Lin, Yasuhiro Itagaki, and Tsuyoshi Fujita. "Synthesis of Conjugated Helical Acetylene-Bridged Polymers and Cyclophanes." Journal of Organic Chemistry 63, no. 6 (1998): 2031–38. http://dx.doi.org/10.1021/jo972101u.

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50

Kang, G. J., and T. H. Chan. "Synthesis and stereochemistry of meta-cyclophanes with intraannular substituents." Journal of Organic Chemistry 50, no. 4 (1985): 452–57. http://dx.doi.org/10.1021/jo00204a005.

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