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Journal articles on the topic 'Indanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

Khoroshilova, Olesya V., and Aleksander V. Vasilyev. "Synthesis of 1-Trifluorometylindanes and Close Structures: A Mini Review." Organics 2, no. 4 (2021): 348–64. http://dx.doi.org/10.3390/org2040019.

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This review describes methods for the synthesis of 1-trifluomethylindanes and close structures, which are still quite rare and scarcely available compounds. There are two main approaches to obtain 1-CF3-indanes. The first one is the construction of an indane system from CF3 precursors; the main methods are acid-mediated Friedel–Crafts cyclization, transition metal-catalyzed [3+2] annulation, and free-radical transformations. The second approach is the trifluoromethylation of a ready-made indane core by various CF3 sources, such as Ruppert–Prakash or Togni reagents. Many of these synthetic proc

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2

Borie, Cyril, Lutz Ackermann, and Malek Nechab. "Enantioselective syntheses of indanes: from organocatalysis to C–H functionalization." Chemical Society Reviews 45, no. 5 (2016): 1368–86. http://dx.doi.org/10.1039/c5cs00622h.

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The indanyl core is ubiquitous in a large variety of drugs and natural products. Remarkable recent progress has been accomplished in the step-economical assembly of functionalization of chiral indanes by means of enantioselective catalysis, with major progress being achieved in organocatalysis and C–H activation chemistry.

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3

Zarl, Elisabeth, Jörg H. Albering, Roland C. Fischer, et al. "Tin-containing Indane and Tetralin Derivatives." Zeitschrift für Naturforschung B 64, no. 11-12 (2009): 1591–97. http://dx.doi.org/10.1515/znb-2009-11-1244.

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The preparation of tin-containing indane and tetralin derivatives via two different reaction pathways is reported. The first route is the reaction of dichlorostannanes or bis(fluoroalkylsulfonyl)stannanes withα,α'-di(chloromagnesium)xylene. The second reaction is the direct coupling of chlorostannanes and α,α'-dichloroxylene which always yields a mixture of tin-containing indanes and tetralins. The separation of these compounds can easily be achieved by fractional crystallization. By these simple and effective routes the first 2,3-distannatetralins were synthesized

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4

Silva, Ana L. R., Paula M. V. Gama, and Maria D. M. C. Ribeiro da Silva. "Influence of the functional groups −NH2, −OCH3, and −OH on the thermochemistry of indanes." Canadian Journal of Chemistry 97, no. 11 (2019): 788–94. http://dx.doi.org/10.1139/cjc-2019-0257.

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This work is a contribution to the thermochemical characterization of bicyclic hydrocarbons, reporting the study of six indane derivatives: 4-aminoindane, 5-aminoindane, 5-methoxyindane, 1-indanol, 2-indanol, and 5-indanol. The combustion calorimetry technique was used to measure the massic energy of combustion of each compound in the condensed state, which has been used to derive the corresponding standard (p° = 0.1 MPa) molar enthalpy of formation, at 298.15 K. The standard molar enthalpies of sublimation or vaporization of the compounds were determined by high-temperature Calvet microcalori

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5

Alesso, Elba N., Dora G. Tombari, Adriana F. Ibañez, Graciela Y. Moltrasio Iglesias, and José M. Aguirre. "Synthesis and nuclear magnetic resonance spectroscopy of indane structures: indanes mono- and disubstituted in the pentagonal ring." Canadian Journal of Chemistry 69, no. 7 (1991): 1166–70. http://dx.doi.org/10.1139/v91-174.

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Indanes monosubstituted and 1,2- and 1,3-disubstituted in the pentagonal ring were synthesized, and configurations were assigned to the 1,2-disubstituted compounds by means of nuclear magnetic resonance spectroscopy. Key words: mono- and disubstituted indanes, conformation, configuration, 1H and 13C NMR, synthesis.

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6

Fan, Yi Chiao, and Ohyun Kwon. "Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine–Palladium Catalysis." Organic Letters 17, no. 9 (2015): 2058–61. http://dx.doi.org/10.1021/acs.orglett.5b00554.

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7

Feng, Ze-Nan, Jin-Yun Luo, Yang Zhang, Guang-Fen Du, and Lin He. "N-Heterocyclic carbene-catalyzed diastereoselective synthesis of sulfenylated indanes via sulfa-Michael–Michael (aldol) cascade reactions." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4700–4704. http://dx.doi.org/10.1039/c9ob00210c.

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8

Iakovenko, Roman O., Anna N. Kazakova, Vasiliy M. Muzalevskiy, et al. "Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands." Organic & Biomolecular Chemistry 13, no. 33 (2015): 8827–42. http://dx.doi.org/10.1039/c5ob01072a.

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9

Parker, Stewart F., Lisha Zhong, Marco Harig, and Dietmar Kuck. "Spectroscopic characterisation of centropolyindanes." Physical Chemistry Chemical Physics 21, no. 8 (2019): 4568–77. http://dx.doi.org/10.1039/c8cp07311b.

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10

Wang, Yuhuang, Xingxing Wu, and Yonggui Robin Chi. "Synthesis of indanes via carbene-catalyzed single-electron-transfer processes and cascade reactions." Chem. Commun. 53, no. 87 (2017): 11952–55. http://dx.doi.org/10.1039/c7cc07208b.

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11

Matsuda, Takanori, and Shoichi Watanuki. "Rhodium-catalysed arylative annulation of 1,4-enynes with arylboronic acids." Organic & Biomolecular Chemistry 13, no. 3 (2015): 702–5. http://dx.doi.org/10.1039/c4ob02210f.

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12

Fan, Yi Chiao, and Ohyun Kwon. "ChemInform Abstract: Synthesis of Functionalized Alkylidene Indanes and Indanones Through Tandem Phosphine-Palladium Catalysis." ChemInform 46, no. 37 (2015): no. http://dx.doi.org/10.1002/chin.201537115.

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13

Hu, Ming, Ling-Yu Guo, Ying Han, Fang-Lin Tan, Ren-Jie Song, and Jin-Heng Li. "Intermolecular cascade annulations of N-(arylsulfonyl)acrylamides with dual C(sp3)–H bonds: divergent access to indanes and pyrrolidin-2-ones." Chemical Communications 53, no. 45 (2017): 6081–84. http://dx.doi.org/10.1039/c7cc02608k.

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14

Feng, Ziwen, Zhenbo Yuan, Xiaobin Zhao, Yue Huang, and Hequan Yao. "A [4 + 1] annulation of ortho-electrophile-substituted para-quinone methides for the synthesis of indanes and isoindolines." Organic Chemistry Frontiers 6, no. 20 (2019): 3535–39. http://dx.doi.org/10.1039/c9qo00977a.

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Indanes and isoindolines were obtained via a 1,6-conjugated addition/1,4-Michael addition of ortho-electrophile-substituted para-quinone methides with nucleophiles in high yields and with good functional group tolerance.

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15

Liu, Bing, Haile Qiu, Xiaofeng Chen, Wenbo Li, and Junliang Zhang. "Copper-catalyzed asymmetric tandem borylative addition and aldol cyclization." Organic Chemistry Frontiers 7, no. 17 (2020): 2492–98. http://dx.doi.org/10.1039/d0qo00654h.

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A highly enantioselective asymmetric copper-catalyzed tandem conjugate addition/aldol cyclization of electron-deficient olefins with B<sub>2</sub>pin<sub>2</sub> was developed, which provided a rapid access to indanes bearing three consecutive chiral stereogenic centers.

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16

Loro, Camilla, Julie Oble, Francesca Foschi, et al. "Acid-mediated decarboxylative C–H coupling between arenes and O-allyl carbamates." Organic Chemistry Frontiers 9, no. 6 (2022): 1711–18. http://dx.doi.org/10.1039/d2qo00114d.

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Treatment of O-allyl N-tosyl carbamates with arenes in the presence of Cu(OTf)2 or TMSOTf as promoters affords N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the promoter.

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17

Zerov, Aleksey V., Anastasia A. Bulova, Olesya V. Khoroshilova, and Aleksander V. Vasilyev. "TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes." Organic Chemistry Frontiers 6, no. 18 (2019): 3264–68. http://dx.doi.org/10.1039/c9qo00822e.

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Novel synthesis of 1,3-diaryl-1-trifluoromethyl indanes, having predominantly a trans-configuration of aryl groups, was developed on the basis of the reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols with arenes in superacid TfOH.

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18

Kotha, Sambasivarao, and Ethirajan Manivannan. "Synthesis of spiro-indanes by cycloaddition strategy." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (October 1, 2001): 2543–47. http://dx.doi.org/10.1039/b106280h.

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19

Ly, Thi-My, Béatrice Quiclet-Sire, Benoît Sortais, and Samir Z. Zard. "A convergent approach to indolines and indanes." Tetrahedron Letters 40, no. 13 (1999): 2533–36. http://dx.doi.org/10.1016/s0040-4039(99)00286-5.

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20

Chang, Meng-Yang, Yan-Shin Wu, Yu-Lin Tsai, and Hsing-Yin Chen. "Synthesis of 2-Sulfonyl Indenes and Indanes." Journal of Organic Chemistry 84, no. 18 (2019): 11699–723. http://dx.doi.org/10.1021/acs.joc.9b01606.

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21

Chan, Kit, Neil Frankish, Tao Zhang, et al. "Bioactive indanes: insight into the bioactivity of indane dimers related to the lead anti‐inflammatory molecule PH46A." Journal of Pharmacy and Pharmacology 72, no. 7 (2020): 927–37. http://dx.doi.org/10.1111/jphp.13269.

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22

Lantaño, B., L. Finkielsztein, E. Alesso, J. Aguirre, and G. Moltrasio. "Synthesis of Indanes Via a [3+2] Cycloaddition." Molecules 5, no. 12 (2000): 416–17. http://dx.doi.org/10.3390/50300416.

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23

Li, Wen-Sen, and John Thottathil. "Fluoride-catalyzed intramolecular denitrocyclization of nitrotoluenes to indanes." Tetrahedron Letters 35, no. 36 (1994): 6595–98. http://dx.doi.org/10.1016/s0040-4039(00)73444-7.

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24

Zhang, Cong, Daniel Bourgin, and Reinhart Keese. "Photochemistry of substituted 1-(but-3-enyl)-indanes." Tetrahedron 47, no. 18-19 (1991): 3059–74. http://dx.doi.org/10.1016/s0040-4020(01)96035-1.

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25

Hanessian, Stephen, and Jianguo Ma. "From glyceraldehyde to functionalized enantiopure tetrahydronaphthalenes and indanes." Tetrahedron Letters 42, no. 50 (2001): 8785–88. http://dx.doi.org/10.1016/s0040-4039(01)01914-1.

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26

Khan, Zulfiqar A., Michio Iwaoka, and Thomas Wirth. "Novel cyclization cascades to functionalized indanes and tetrahydronaphthalenes." Tetrahedron 66, no. 33 (2010): 6639–46. http://dx.doi.org/10.1016/j.tet.2010.03.062.

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27

Zieba, Andrzej, and Joel F. Hooper. "Palladium‐Catalysed Carboborylation for the Synthesis of Borylated Indanes." European Journal of Organic Chemistry 2021, no. 29 (2021): 4072–75. http://dx.doi.org/10.1002/ejoc.202100309.

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28

Saltiel, Jack, Shipra Gupta, David W. Eaker, Andrew M. Kropp, and V. K. Ratheesh Kumar. "Photochemistry and Photophysics of the 3-Styrylidenebenz[e]indanes." Photochemistry and Photobiology 94, no. 2 (2018): 247–60. http://dx.doi.org/10.1111/php.12849.

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29

NUMAO, Naganori, Yukiko HIROTA, Akiyo IWAHORI, et al. "Biological Activities of 1,1,6-Trisubstituted Indanes: Beyond Magainin 2." Biological & Pharmaceutical Bulletin 22, no. 1 (1999): 73–76. http://dx.doi.org/10.1248/bpb.22.73.

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30

Gabriele, Bartolo, Raffaella Mancuso, and Lucia Veltri. "Recent Advances in the Synthesis of Indanes and Indenes." Chemistry - A European Journal 22, no. 15 (2016): 5056–94. http://dx.doi.org/10.1002/chem.201503933.

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31

Nöth, Heinrich, and Thomas Seifert. "Hydrazino Derivatives of Gallanes and Indanes − Synthesis and Structures." European Journal of Inorganic Chemistry 2002, no. 3 (2002): 602–12. http://dx.doi.org/10.1002/1099-0682(200203)2002:3<602::aid-ejic602>3.0.co;2-i.

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32

Alesso, Elba N., Dora G. Tombari, Graciela Y. Moltrasio Iglesias, and José M. Aguirre. "Reactions of some N-acyl-1-alkylamines with poly phosphoric ester PPE: nuclear magnetic resonance and stereochemistry of reaction products." Canadian Journal of Chemistry 65, no. 11 (1987): 2568–74. http://dx.doi.org/10.1139/v87-427.

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Phenylindanes were obtained from the reaction of N-acyl-1-arylalkylamines with polyphosphoric ester (PPE). cis-1-Methyl-3-(3,4-dimethoxyphenyl)-5,6-dimethoxyindane was synthesized to determine which stereoisomer was produced by N-formyl and N-acetyl-1-(3,4-dimethoxyphenyl)ethylamine with PPE. Nuclear magnetic resonance specra (1H and 13C) of several mono-, 1,3-di-, and 1,2,3-tri-substituted indanes were fully analyzed to provide information on steric interactions and conformation of the cyclopentene ring. Possible cyclodimerization pathways are proposed.

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33

Suresh, Rajendran, Shanmugam Muthusubramanian, Muthusamy Boominathan та Govindaswamy Manickam. "Acid controlled generation of indanes and oxazolines from β-hydroxyarylethanamide". Tetrahedron Letters 54, № 19 (2013): 2315–20. http://dx.doi.org/10.1016/j.tetlet.2013.02.033.

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34

Sánchez-Larios, Eduardo, and Michel Gravel. "Diastereoselective Synthesis of Indanes via a Domino Stetter−Michael Reaction." Journal of Organic Chemistry 74, no. 19 (2009): 7536–39. http://dx.doi.org/10.1021/jo901468h.

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35

LI, W. S., and J. THOTTATHIL. "ChemInform Abstract: Fluoride-Catalyzed Intramolecular Denitrocyclization of Nitrotoluenes to Indanes." ChemInform 26, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199505065.

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36

Zhang, Lei, and James W. Herndon. "Synthesis of Indanes through Coupling of Ethynylstyrene Derivatives with Carbene Complexes." Organometallics 23, no. 6 (2004): 1231–35. http://dx.doi.org/10.1021/om034334j.

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37

Sheridan, H., S. Lemon, N. Frankish, et al. "Synthesis and antispasmodic activity of nature identical substituted indanes and analogues." European Journal of Medicinal Chemistry 25, no. 7 (1990): 603–8. http://dx.doi.org/10.1016/0223-5234(90)90185-6.

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38

Harrowven, David C., and Rory Browne. "A triple umpolung sequence for the preparation of highly substituted indanes." Tetrahedron 52, no. 47 (1996): 14951–60. http://dx.doi.org/10.1016/0040-4020(96)00907-6.

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39

Begouin, Jeanne-Marie, Francesca Capitta, Xian Wu, and Meike Niggemann. "Diastereoselective Synthesis of Indanes and Tetralins via Intramolecular Friedel–Crafts Reaction." Organic Letters 15, no. 6 (2013): 1370–73. http://dx.doi.org/10.1021/ol400341p.

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40

Casey, Mike, Zelda Appelbe, Claire M. Keaveney, and Cornelius J. Kelly. "A Novel Method for the Stereoselective Synthesis of Tetralins and Indanes." Synlett 2002, no. 9 (2002): 1404–8. http://dx.doi.org/10.1055/s-2002-33514.

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41

Rommens, Johan, Mark van der Auweraer, Frans C. De Sclryver, and Paul M. Borsenberger. "A new class of electron transport compounds: 1,3-bis-dicyanomethylene indanes." Advanced Materials 7, no. 6 (1995): 574–76. http://dx.doi.org/10.1002/adma.19950070615.

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42

Fischer, Roland A., Joachim Behm, Thomas Priermeier, and Wolfgang Scherer. "Transition-Metal-Substituted Volatile Alanes, Gallanes, and Indanes: Synthesis and Structure." Angewandte Chemie International Edition in English 32, no. 5 (1993): 746–48. http://dx.doi.org/10.1002/anie.199307461.

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43

Wu, Xiang, Shu-Sen Chen, Ling Zhang, Hai-Jun Wang, and Liu-Zhu Gong. "Palladium-catalyzed enantioselective carboannulation of 1,3-dienes with aryl iodides enables access to chiral indanes." Chemical Communications 54, no. 69 (2018): 9595–98. http://dx.doi.org/10.1039/c8cc04641g.

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44

Reddel, Jordan C. T., Weiwei Wang, Kalli Koukounas, and Regan J. Thomson. "Triflimide-catalyzed allylsilane annulations of benzylic alcohols for the divergent synthesis of indanes and tetralins." Chemical Science 8, no. 3 (2017): 2156–60. http://dx.doi.org/10.1039/c6sc04762a.

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45

Cacciuttolo, Bastien, Pierrick Ondet, Sophie Poulain-Martini, Gilles Lemière, and Elisabet Duñach. "Bi(OTf)3-catalysed synthesis of substituted indanes by a double hydroarylation of unactivated 1,3-dienes." Org. Chem. Front. 1, no. 7 (2014): 765–69. http://dx.doi.org/10.1039/c4qo00149d.

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46

Hu, Wanyao, Cong Zhang, Jie Huang, Yingying Guo, Zhenqian Fu та Wei Huang. "Access to Highly Functionalized Indanes from Arynes and α,γ-Diketo Esters". Organic Letters 21, № 4 (2019): 941–45. http://dx.doi.org/10.1021/acs.orglett.8b03919.

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47

Roberts, Lee R., Matthew S. Corbett, Steven J. Fussell та ін. "A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists". Tetrahedron Letters 56, № 47 (2015): 6546–50. http://dx.doi.org/10.1016/j.tetlet.2015.10.004.

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48

Bowers, Nigel I., Derek R. Boyd, Narain D. Sharma, et al. "Stereoselective benzylic hydroxylation of 2-substituted indanes using toluene dioxygenase as biocatalyst." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1999): 1453–62. http://dx.doi.org/10.1039/a901453e.

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49

Kuo, Chih-Wei, and Jim-Min Fang. "SYNTHESIS OF XANTHENES, INDANES, AND TETRAHYDRONAPHTHALENES VIA INTRAMOLECULAR PHENYL–CARBONYL COUPLING REACTIONS." Synthetic Communications 31, no. 6 (2001): 877–92. http://dx.doi.org/10.1081/scc-100103323.

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50

Devineau, Alice, Mathilde Grosbois, Isabelle Carletti, and Bernard Vacher. "Synthetic Studies on Cyclobuta[a]indanes: Stereocontrolled Access to C9-Substituted Derivatives." Journal of Organic Chemistry 74, no. 2 (2009): 757–63. http://dx.doi.org/10.1021/jo802177d.

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