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Journal articles on the topic 'Isochromans'

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Author: Grafiati

Published: 20 July 2024

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1

Hamada, Shohei, Kyoko Yano, Ayano Ohshimo, Elghareeb E. Elboray, Yusuke Kobayashi, and Takumi Furuta. "Oxidative C–N Bond Formation of Isochromans Using an Electronically Tuned Nitroxyl Radical as Catalyst." SynOpen 08, no. 02 (May 2024): 125–29. http://dx.doi.org/10.1055/s-0040-1720118.

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AbstractThe cross-dehydrogenative coupling between isochromans and nucleophiles using an electronically tuned nitroxyl radical catalyst, which effectively promotes the oxidation of benzylic ethers, has been investigated. Using sulfonamides as a nucleophile, modification of isochromans via oxidative C–N bond formation has been achieved at ambient temperature.

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2

Liu, Shiyao, Kazunari Nakajima, and Yoshiaki Nishibayashi. "Copper-catalysed enantioselective intramolecular etherification of propargylic esters: synthetic approach to chiral isochromans." RSC Advances 9, no. 33 (2019): 18918–22. http://dx.doi.org/10.1039/c9ra03880a.

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3

Trefiletti, Giuliana, Anna Rita Togna, Valentina Latina, Carolina Marra, Marcella Guiso, and Giuseppina I. Togna. "1-Phenyl-6,7-dihydroxy-isochroman suppresses lipopolysaccharide-induced pro-inflammatory mediator production in human monocytes." British Journal of Nutrition 106, no. 1 (January 27, 2011): 33–36. http://dx.doi.org/10.1017/s0007114510005763.

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Extra-virgin olive oil is an integral ingredient of the Mediterranean diet, and it has been suggested that its high consumption has beneficial effects on human health. Its protective effect, in particular against the development of CVD, has been related not only to the high content of oleic acid, but also to the antioxidant and anti-inflammatory properties of polyphenols. In order to verify the anti-inflammatory and anti-atherogenic properties of hydroxy-isochromans, a class of ortho-diphenols present in extra-virgin olive oil, we investigated the potential ability of 1-phenyl-6,7-dihydroxy-isochroman (L137) to modulate the production of key inflammatory mediators by human monocytes, by evaluating its in vitro effects on prostanoid (thromboxane A2 and PGE2) and cytokine (TNF-α) production. Its effect on the protein expression of the inducible form of cyclo-oxygenase-2 (COX-2), a pro-inflammatory enzyme responsible for elevated prostanoid levels, was also explored. The results showed that L137 significantly inhibited both prostanoid and TNF-α production in lipopolysaccharide-primed human monocytes in a dose-dependent manner, by inhibiting the COX activity of COX-2. We also demonstrated that the effects of the isochroman are mediated, at least partly, through the suppression of NF-κB activation leading to the down-regulation of the synthesis of COX-2.

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4

UNTERHALT, B., and R. JOESTINGMEIER. "ChemInform Abstract: New Substituted Isochromans." ChemInform 28, no. 1 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199701169.

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5

Verma, Ashish Kumar, Ande Chennaiah, Sateesh Dubbu, and Yashwant D. Vankar. "Stereoselective synthesis of sugar-fused (or 1,2-annulated) isochromans and isochromanones by using oxa-Pictet–Spengler reaction." Organic & Biomolecular Chemistry 16, no. 37 (2018): 8258–62. http://dx.doi.org/10.1039/c8ob01698d.

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6

Thatikonda, Thanusha, Siddharth K. Deepake, Pawan Kumar, and Utpal Das. "α-Angelica lactone catalyzed oxidation of benzylic sp3 C–H bonds of isochromans and phthalans." Organic & Biomolecular Chemistry 18, no. 21 (2020): 4046–50. http://dx.doi.org/10.1039/d0ob00729c.

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7

Nickerson, Leslie A., Benjamin D. Bergstrom, Mingchun Gao, Yuan-Shin Shiue, Croix J. Laconsay, Matthew R. Culberson, Walker A. Knauss, James C. Fettinger, Dean J. Tantillo, and Jared T. Shaw. "Correction: Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes." Chemical Science 11, no. 19 (2020): 5113. http://dx.doi.org/10.1039/d0sc90081h.

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Correction for ‘Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes’ by Leslie A. Nickerson et al., Chem. Sci., 2020, 11, 494–498, DOI: 10.1039/C9SC05111B.

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8

Unterhalt, B., and U. Heppert. "ChemInform Abstract: Isochromans Related to Fluoxetin." ChemInform 32, no. 38 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200138108.

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9

Zhu, Zhengbo, Alafate Adili, Chenfei Zhao, and Daniel Seidel. "Catalytic Enantioselective Approaches to the oxa-Pictet–Spengler Cyclization and Other 3,6-Dihydropyran-Forming Reactions." SynOpen 03, no. 03 (July 2019): 77–90. http://dx.doi.org/10.1055/s-0039-1690686.

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This Short Review provides an analysis of the state-of-the-art in catalytic enantioselective oxa-Pictet–Spengler cyclizations. Also discussed are other catalytic reactions providing access to enantioenriched isochromans and tetrahydropyrano[3,4-b]indoles. Context is provided and remaining challenges are highlighted.

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10

Yang, Guoping, Ke Li, Kai Zeng, Yijin Li, Tao Yu, and Yufeng Liu. "Heteropolyacid ionic liquid heterogeneously catalyzed synthesis of isochromans via oxa-Pictet–Spengler cyclization in dimethyl carbonate." RSC Advances 11, no. 18 (2021): 10610–14. http://dx.doi.org/10.1039/d1ra01004b.

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An efficient heterogeneous and green catalyst [HEMTH]H₂[PMo₁₂O₄₀] was prepared to catalysis the oxa-Pictet–Spengler cyclization of arylethanols and aldehydes to afford isochromans with excellent yields using dimethyl carbonate as a green solvent.

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11

Huo, Congde, Mingxia Wu, Fengjuan Chen, Xiaodong Jia, Yong Yuan, and Haisheng Xie. "Catalytic amounts of CBr4 mediated dehydrogenative coupling of isochromans with aromatic ketones." Chemical Communications 51, no. 22 (2015): 4708–11. http://dx.doi.org/10.1039/c4cc09922b.

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In the presence of catalytic amounts of CBr₄ (a metal-free mediator), an unexpected oxidative dehydrogenative coupling of isochromans with ketones occurred to construct new C^sp3–C^sp3 bonds. The reactions were performed under simple solvent-free aerobic conditions.

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12

Ahmar, M., and R. Bloch. "A New Synthesis of Isochromans and Phtalans." Synthetic Communications 22, no. 10 (May 1992): 1417–20. http://dx.doi.org/10.1080/00397919208021607.

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13

McMullin, David R., Tienabe K. Nsiama, and J. David Miller. "Isochromans and α-Pyrones from Penicillium corylophilum." Journal of Natural Products 77, no. 2 (January 23, 2014): 206–12. http://dx.doi.org/10.1021/np4005486.

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14

Guiso, Marcella, Carolina Marra, and Claudia Cavarischia. "Isochromans from 2-(3′,4′-dihydroxy)phenylethanol." Tetrahedron Letters 42, no. 37 (September 2001): 6531–34. http://dx.doi.org/10.1016/s0040-4039(01)01307-7.

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15

Togna, Giuseppina I., Anna Rita Togna, Matteo Franconi, Carolina Marra, and Marcella Guiso. "Olive Oil Isochromans Inhibit Human Platelet Reactivity." Journal of Nutrition 133, no. 8 (August 1, 2003): 2532–36. http://dx.doi.org/10.1093/jn/133.8.2532.

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16

Vankar, Yashwant, Parasuraman Rajasekaran, and Yakkala Mallikharjunarao. "Synthesis of 1C-Aryl/Alkyl 2C-Branched Sugar-Fused Isochroman Derivatives by Sequential Prins and Friedel–Crafts Cyclizations on a Perlin Aldehyde Derived Substrate." Synlett 28, no. 11 (March 9, 2017): 1346–52. http://dx.doi.org/10.1055/s-0036-1588156.

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The synthesis of C-aryl/alkyl 2C-branched sugar-fused isochromans by using a carbohydrate-derived starting material is described. Our approach makes use of sequential Prins and Friedel–Crafts cyclizations in which a Perlin aldehyde derived homoallylic alcohol is converted into the target molecule. This strategy works well with many aldehydes and gives good yields with excellent selectivity.

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17

Khilya, V., O. Shablykina, M. Tsapko, S. Shilin, V. Moskvina, H. Bubela, and Yu Zabolotna. "Eu(fod)3 EFFECT ON 1H NMR SPECTRA OF 3-ARYLISOCOUMARINS AND 3-ARYL-3,4-DIHYDROISOCOUMARINS WITH ALKOXY, ESTER AND AMIDE GROUPS." Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, no. 2(54) (2017): 74–80. http://dx.doi.org/10.17721/1728-2209.2017.2(54).15.

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The effect of the lanthanide shift reagent (LSR) – tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octa-dionate) of Europium – Eu(fod)3 – on 1H NMR spectra of functionalized 3-arylisocoumarins and 3-aryl-3,4-dihydroisocoumarins was investigated. Based on previous studies of LSR interactions with benzopyrones, it was expected that the main coordination centre for the Eu3+ would be the exocyclic Oxygen atom of the heterocycle, but the possibility of competition from aromatic substituent functional groups was also considered. By measuring lanthanide-induced shifts (LIS) of the proton signals of the molecules at different ratios of substrate and Eu(fod)3, specific LIS values were determined. Based on those, it was concluded that the main direction of LSR coordination with 3-(2-hydroxy-5-methylphenyl)-1Hisochromen-1-one, 3-(2-methoxy-5-methylphenyl)-1H-isochromen-1-one and 3-(2-methoxy-5-methylphenyl)isochroman-1-one is the exocyclic Oxygen atom of the heterocycle, because the maximum LIS were recorded for the H-8 atom of isochromone system of these derivatives. In the case of ethyl ester of [2-(4-(1-oxo-1H-isochromen-3-yl)phenoxy] acetic acid and methyl ester of [2-(4-(1-oxoisochroman-3-yl)phenoxy]acetic acid comparable LIS values were observed both for H-8 and for the methylene group of the hydroxyacetic acid fragment, therefore, in such molecules the coordination of the Eu3+ to the heterocycle or to the aliphatic ester group is almost equally probable. In spectrum of methyl ester of N-{[4-(1-oxo-1H-isochromen-3-yl)phenoxy]acetyl}valine and N-{[4-(1-oxoisochroman-3-yl)-phenoxy]acetyl}valine there are insignificant LIS of H-8; and the maximum LIS were observed for the signals of the protons neighboring the two carbonyl groups of hydroxyacetic acid and valine fragments. Thus, these compounds interact w

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18

Yus, Miguel, Francisco Foubelo, and Daniel García. "Cyclic Acetals as Precursors of Substituted Isochromans and Naphthoxepines." HETEROCYCLES 74, no. 1 (2007): 507. http://dx.doi.org/10.3987/com-07-s(w)29.

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19

Mao, Ying, Min Cao, Xiaoguang Pan, Jiancheng Huang, Jing Li, Liren Xu, and Lei Liu. "Bimolecular oxidative C–H alkynylation of α-substituted isochromans." Organic Chemistry Frontiers 6, no. 12 (2019): 2028–31. http://dx.doi.org/10.1039/c9qo00352e.

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20

Zhou, Mei-Yan, Shan-Shan Kong, Ling-Qiong Zhang, Ming Zhao, Jin-Ao Duan, Zhen Ou-yang, and Min Wang. "CuBr2 catalyzed bromination/oxidation of isochromans to benzaldehyde derivatives." Tetrahedron Letters 54, no. 30 (July 2013): 3962–64. http://dx.doi.org/10.1016/j.tetlet.2013.05.078.

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21

AHMAR, M., and R. BLOCH. "ChemInform Abstract: A New Synthesis of Isochromans and Phthalans." ChemInform 23, no. 38 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199238161.

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22

Leibeling, Markus, Dennis C. Koester, Martin Pawliczek, Svenia C. Schild, and Daniel B. Werz. "Domino access to highly substituted chromans and isochromans from carbohydrates." Nature Chemical Biology 6, no. 3 (January 24, 2010): 199–201. http://dx.doi.org/10.1038/nchembio.302.

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23

Dammacco, Mariangela, Leonardo Degennaro, Saverio Florio, Renzo Luisi, Biagia Musio, and Angela Altomare. "Lithiation ofN-Alkyl-(o-tolyl)aziridine: Stereoselective Synthesis of Isochromans§." Journal of Organic Chemistry 74, no. 16 (August 21, 2009): 6319–22. http://dx.doi.org/10.1021/jo9011943.

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24

Guiso, Marcella, Carolina Marra, and Rocio Rodriguez Arcos. "An investigation on dihydroxy-isochromans in extra virgin olive oil." Natural Product Research 22, no. 16 (November 10, 2008): 1403–9. http://dx.doi.org/10.1080/14786410701823942.

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25

Zhou, Mei-Yan, Shan-Shan Kong, Ling-Qiong Zhang, Ming Zhao, Jin-Ao Duan, Ou-yang Zhen, and Min Wang. "ChemInform Abstract: CuBr2Catalyzed Bromination/Oxidation of Isochromans to Benzaldehyde Derivatives." ChemInform 44, no. 44 (October 14, 2013): no. http://dx.doi.org/10.1002/chin.201344065.

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26

Chen, Yan, and Shi-Kai Tian. "Decarboxylative Alkylation ofβ-Keto Acids with Isochromans under Oxidative Conditions." Chinese Journal of Chemistry 31, no. 1 (December 27, 2012): 37–39. http://dx.doi.org/10.1002/cjoc.201200994.

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27

Alavala, Gopi Krishna Reddy, Farrukh Sajjad, Taoda Shi, Zhenghui Kang, Mingliang Ma, Dong Xing, and Wenhao Hu. "Diastereoselective synthesis of isochromans via the Cu(ii)-catalysed intramolecular Michael-type trapping of oxonium ylides." Chemical Communications 54, no. 89 (2018): 12650–53. http://dx.doi.org/10.1039/c8cc06390g.

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28

Wei, Xiaoyi, Liangxiong Xu, Jinghua Xue, Hanhong Xu, Xingzhong Liu, and Wenzhe Ma. "Three New Isochromans from the Mycelial Culture of a Cylindrocarpon Fungus." HETEROCYCLES 68, no. 9 (2006): 1955. http://dx.doi.org/10.3987/com-06-10799.

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29

Petrone, David A., Hasnain A. Malik, Antonin Clemenceau, and Mark Lautens. "Functionalized Chromans and Isochromans via a Diastereoselective Pd(0)-Catalyzed Carboiodination." Organic Letters 14, no. 18 (September 6, 2012): 4806–9. http://dx.doi.org/10.1021/ol302111y.

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30

Wang, Zhong, Peng Fan, Tong-Dan Xue, Lin-Lin Meng, Wen-Bin Gao, Jun Zhang, You-xing Zhao, and Du-Qiang Luo. "Two New Isocoumarin Derivatives from an Endophytic Fungi Pestalotiopsis coffeae Isolated from a Mangrove Fishtail Palm." Natural Product Communications 13, no. 1 (January 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300117.

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Two new isocoumarin derivatives, 6,8-dihydroxy-7-methyl-1-oxo-1H-isochromene-3-carboxylic acid (1) and 6,8-dihydroxy-3-methoxy-3,7- dimethyl-isochroman-1-one (2), together with five known compounds (3-7), were isolated from the endophytic fungus Pestalotiopsis coffeae derived from the Chinese plant fishtail palm. The structures of these compounds were determined mainly by analysis of their NMR spectroscopic data. The structure of compound 2 was further confirmed by X-ray diffraction.

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31

Ammann, Stephen E., Grant T. Rice, and M. Christina White. "Terminal Olefins to Chromans, Isochromans, and Pyrans via Allylic C–H Oxidation." Journal of the American Chemical Society 136, no. 31 (July 16, 2014): 10834–37. http://dx.doi.org/10.1021/ja503322e.

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32

Hegedüs, Adrienn, and Zoltán Hell. "Zeolite-catalyzed simple synthesis of isochromans via the oxa-Pictet–Spengler reaction." Organic & Biomolecular Chemistry 4, no. 7 (2006): 1220. http://dx.doi.org/10.1039/b601314g.

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33

Zhou, Jimei, Chao Wang, Dong Xue, Weijun Tang, Jianliang Xiao, and Chaoqun Li. "Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization." Tetrahedron 74, no. 49 (December 2018): 7040–46. http://dx.doi.org/10.1016/j.tet.2018.10.028.

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34

Temperini, Andrea, Anna Barattucci, Paola Maria Bonaccorsi, Ornelio Rosati, and Lucio Minuti. "Stereoselective Synthesis of Substituted Tetrahydropyrans and Isochromans by Cyclization of Phenylseleno Alcohols." Journal of Organic Chemistry 80, no. 16 (August 11, 2015): 8102–12. http://dx.doi.org/10.1021/acs.joc.5b01199.

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35

Liu, Jian, Elizabeth T. Birzin, Wanda Chan, Yi Tien Yang, Lee-Yuh Pai, Carolyn DaSilva, Edward C. Hayes, et al. "Estrogen receptor ligands. Part 11: Synthesis and activity of isochromans and isothiochromans." Bioorganic & Medicinal Chemistry Letters 15, no. 3 (February 2005): 715–18. http://dx.doi.org/10.1016/j.bmcl.2004.11.018.

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36

Cui, Jian-Fang, Bin Yang, Qiong Yu, Nathanael Chun-Him Lai, Han Chen, and Man-Kin Wong. "Silver-Mediated Organic Transformations of Propargylamines to Enones, α-Thioketones, and Isochromans." ChemistrySelect 4, no. 4 (January 29, 2019): 1476–82. http://dx.doi.org/10.1002/slct.201900024.

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37

Leibeling, Markus, Bastian Milde, Daniel Kratzert, Dietmar Stalke, and Daniel B. Werz. "Intermolecular Twofold Carbopalladation/Cyclization Sequence to Access Chromans and Isochromans from Carbohydrates." Chemistry - A European Journal 17, no. 36 (August 2, 2011): 9888–92. http://dx.doi.org/10.1002/chem.201101917.

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38

Kock, Ines, Siegfried Draeger, Barbara Schulz, Brigitta Elsässer, Tibor Kurtán, Ágnes Kenéz, Sándor Antus, et al. "Pseudoanguillosporin A and B: Two New Isochromans Isolated from the Endophytic FungusPseudoanguillosporasp." European Journal of Organic Chemistry 2009, no. 9 (March 2009): 1427–34. http://dx.doi.org/10.1002/ejoc.200801083.

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39

Zeh, Michael, Peter Lorenz, Peter Kreutzmann, and Peter Schönfeld. "Hydroxy-1-aryl-isochromans: protective compounds against lipid peroxidation and cellular nitrosative stress." Redox Report 13, no. 1 (February 2008): 23–30. http://dx.doi.org/10.1179/135100008x259123.

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40

Kaufman, Teodoro S., and Enrique L. Larghi. "The Oxa-Pictet-Spengler Cyclization: Synthesis of Isochromans and Related Pyran-Type Heterocycles." Synthesis, no. 2 (2006): 187–220. http://dx.doi.org/10.1055/s-2005-918502.

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41

Bovicelli, Paolo, Anna Sanetti, Roberta Bernini, and Paolo Lupattelli. "Oxyfunctionalisation of activated methylenes by dimethyldioxirane: An easy conversion of isochromans into isocoumarins." Tetrahedron 53, no. 28 (July 1997): 9755–60. http://dx.doi.org/10.1016/s0040-4020(97)00622-4.

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42

Xu, Yao-Chang, Elaine Lebeau, John W. Gillard, and Giorgio Attardo. "Regio- and stereoselective DDQ-induced oxidative coupling of isochromans and isothiochroman with alcohols." Tetrahedron Letters 34, no. 24 (June 1993): 3841–44. http://dx.doi.org/10.1016/s0040-4039(00)79242-2.

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43

Obata, Tomoyuki, Sho Suzuki, Asuka Nakagawa, Ryota Kajihara, Keiichi Noguchi, and Akio Saito. "Gold-Catalyzed Domino Synthesis of Functionalized Benzofurans and Tetracyclic Isochromans via Formal Carboalkoxylation." Organic Letters 18, no. 16 (August 2, 2016): 4136–39. http://dx.doi.org/10.1021/acs.orglett.6b02159.

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44

Hashida, Junko, Megumi Niitsuma, Masato Iwatsuki, Mihoko Mori, Aki Ishiyama, Miyuki Namatame, Aki Nishihara-Tsukashima, et al. "Panowamycins A and B, new antitrypanosomal isochromans produced by Streptomyces sp. K07-0010." Journal of Antibiotics 65, no. 4 (January 25, 2012): 197–202. http://dx.doi.org/10.1038/ja.2011.139.

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45

Huo, Congde, Mingxia Wu, Fengjuan Chen, Xiaodong Jia, Yong Yuan, and Haisheng Xie. "ChemInform Abstract: Catalytic Amounts of CBr4Mediated Dehydrogenative Coupling of Isochromans with Aromatic Ketones." ChemInform 46, no. 29 (July 2015): no. http://dx.doi.org/10.1002/chin.201529194.

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46

Chen, Yan, and Shi-Kai Tian. "ChemInform Abstract: Decarboxylative Alkylation of β-Keto Acids with Isochromans under Oxidative Conditions." ChemInform 44, no. 43 (October 7, 2013): no. http://dx.doi.org/10.1002/chin.201343139.

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47

Petrone, David A., Hasnain A. Malik, Antonin Clemenceau, and Mark Lautens. "ChemInform Abstract: Functionalized Chromans and Isochromans via a Diastereoselective Pd(0)-Catalyzed Carboiodination." ChemInform 44, no. 3 (January 15, 2013): no. http://dx.doi.org/10.1002/chin.201303126.

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48

Syed Abuthahir, S., M. NizamMohideen, S. Mayakrishnan, N. Uma Maheswari, and V. Viswanathan. "Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one." Acta Crystallographica Section E Crystallographic Communications 75, no. 8 (July 9, 2019): 1117–22. http://dx.doi.org/10.1107/s2056989019009435.

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The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C22H17NO2, (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C14H17NO2, (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent molecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intramolecular N—H...O hydrogen bond present forming an S(6) ring motif. In the crystal of I, molecules are linked by N—H...π interactions, forming chains along the b-axis direction. A C—H...π interaction links the chains to form layers parallel to (100). The layers are then linked by a second C—H...π interaction, forming a three-dimensional structure. In the crystal of II, the two independent molecules (A and B) are linked by N—H...O hydrogen bonds, forming –A–B–A–B– chains along the [101] direction. The chains are linked into ribbons by C—H...π interactions involving inversion-related A molecules. The latter are linked by offset π–π interactions [intercentroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure.

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49

Bianco, A., F. Coccioli, M. Guiso, and C. Marra. "The occurrence in olive oil of a new class of phenolic compounds: hydroxy-isochromans." Food Chemistry 77, no. 4 (June 2002): 405–11. http://dx.doi.org/10.1016/s0308-8146(01)00366-1.

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50

Mohler, Debra L., and David W. Thompson. "Synthesis of isochromans via the titanium tetrachloride assisted cyclization of acetals of phenethyl alcohols." Tetrahedron Letters 28, no. 23 (January 1987): 2567–70. http://dx.doi.org/10.1016/s0040-4039(00)96149-5.

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