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Journal articles on the topic 'Claisen rearrangement'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Zhang, Beibei, Xiaoxian Li, Boying Guo, and Yunfei Du. "Hypervalent iodine reagent-mediated reactions involving rearrangement processes." Chemical Communications 56, no. 91 (2020): 14119–36. http://dx.doi.org/10.1039/d0cc05354f.

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We summarize the developments of hypervalent iodine reagents-mediated reactions involving [1,2]-migration, Hofmann rearrangement, Beckmann rearrangement, ring contraction/expansion, [3,3]-sigmatropic/iodonium-Claisen rearrangement and some miscellaneous rearrangements.

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2

K., C. Majumdar, and Bhattacharyya Trijit. "Aza-Claisen rearrangement." Journal of Indian Chemical Society Vol. 79, Feb 2002 (2002): 112–21. https://doi.org/10.5281/zenodo.5840687.

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Department of Chemistry. University of Kalyani, Kalyani-741 235, India E-mail : kcm@klyuniv.ernet.in Fax : 91-033-5828282 <em>Manuscript received 28 February 2001. accepted 20 June 2001</em> This brief review presents an overview on aza-Claisen rearrangement with an emphasis on recent developments, e.g. ketene-aza-Claisen rearrangement, aza-Claisen rearrangement by acid-catalyzed Michael addition and palladium complex-catalyzed aza-Claisen rearrangement etc.

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3

McGeary, Ross, Jed Burns, and Elizabeth Krenske. "Claisen Rearrangements of Benzyl Vinyl Ethers and Heterobenzyl Vinyl Ethers." Synthesis 50, no. 09 (2018): 1750–72. http://dx.doi.org/10.1055/s-0036-1589529.

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The Claisen rearrangement of benzylic substrates (benzyl vinyl ethers) has received considerably less attention than its well-known aliphatic and normal aromatic variants. Here, we review the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use in the synthesis of natural products and drug-like molecules.1 Introduction2 Early Attempts at the Benzyl-Claisen Rearrangement3 Successful Benzylic Examples4 Heterobenzylic Examples5 Conclusion

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4

Ito, Hisanaka, and Takeo Taguchi. "Asymmetric Claisen rearrangement." Chemical Society Reviews 28, no. 1 (1999): 43–50. http://dx.doi.org/10.1039/a706415b.

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5

Takano, Seiichi, Shun’ichi Tomita, Michiyasu Takahashi, and Kunio Ogasawara. "Thionolactone Claisen Rearrangement." Chemistry Letters 16, no. 7 (1987): 1379–80. http://dx.doi.org/10.1246/cl.1987.1379.

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6

Saputra, Rizki Rachmad, Reny Rosalina, Dimas Pramudita, et al. "Claisen Rearrangement Toward Cyclic Compound on Different Organic Synthesis Methods: Short Review." Chempublish Journal 7, no. 2 (2023): 80–87. http://dx.doi.org/10.22437/chp.v7i2.26053.

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The synthesis of functional and complex organic compounds is majorly performed by the Claisen rearrangement method. Claisen rearrangement is one of [3,3] sigmatropic rearrangements, a complex method in the synthesis of organic compounds, where it is mostly used to construct stereoselective compounds. It can be combined with other synthesis methods to synthesize organic compounds giving satisfactory results based on the method used, temperature, time, and yield produced. This review aimed to summarize several recent advances in synthesizing organic compounds through Claisen rearrangement reacti

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7

Krištofíková, Dominika, Juraj Filo, Mária Mečiarová, and Radovan Šebesta. "Why do thioureas and squaramides slow down the Ireland–Claisen rearrangement?" Beilstein Journal of Organic Chemistry 15 (December 10, 2019): 2948–57. http://dx.doi.org/10.3762/bjoc.15.290.

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A range of chiral hydrogen-bond-donating organocatalysts was tested in the Ireland–Claisen rearrangement of silyl ketene acetals. None of these organocatalysts was able to impart any enantioselectivity on the rearrangements. Furthermore, these organocatalysts slowed down the Ireland–Claisen rearrangement in comparison to an uncatalyzed reaction. The catalyst-free reaction proceeded well in green solvents or without any solvent. DFT calculations showed that the activation barriers are higher for reactions involving hydrogen-donating organocatalysts and kinetic experiments suggest that the catal

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8

Jain, Seema. "Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines." Heterocyclic Communications 25, no. 1 (2019): 22–26. http://dx.doi.org/10.1515/hc-2019-0010.

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Abstract7-Allylindolines are valuable synthons for designing biologically active molecular libraries. Lewis acid catalyzed amino-Claisen rearrangement provides a one pot synthetic entry to these heteroarenes. In this context, Zinc chloride (ZnCl2)–N,N-dimethylformamide system efficiently catalyzed amino-Claisen rearrangements of 1-N-allylindolines to 7-allylindolines. The rearrangement is influenced by stereoelectronic effects of substituents present in 1-N-allylindolines. The substrates containing electron donating functionalities underwent rearrangement at lower temperature than substrates w

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9

Gopalan, B., K. Rajagopalan, K. Sunitha, and K. K. Balasubramanian. "Studies in claisen rearrangement." Tetrahedron 41, no. 15 (1985): 3153–59. http://dx.doi.org/10.1016/s0040-4020(01)96670-0.

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10

Ito, Hisanaka, Azusa Sato, and Takeo Taguchi. "Enantioselective aromatic Claisen rearrangement." Tetrahedron Letters 38, no. 27 (1997): 4815–18. http://dx.doi.org/10.1016/s0040-4039(97)01040-x.

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11

Gonda, Jozef. "The Belluš–Claisen Rearrangement." Angewandte Chemie International Edition 43, no. 27 (2004): 3516–24. http://dx.doi.org/10.1002/anie.200301718.

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12

Majumdar, K. C., and S. K. Chattopadhyay. "Synthesis of pyrimidine annulated furothiopyrans An efficient sequential and tandem catalyzed Claisen rearrangement intramolecular hydroaryloxylation." Canadian Journal of Chemistry 84, no. 3 (2006): 469–75. http://dx.doi.org/10.1139/v06-020.

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Regioselective synthesis of a hitherto unreported furothiopyran moiety fused at the C-5 and C-6 positions of a pyrimidine heterocycle was achieved by the application of sequential Claisen rearrangement in which a second aromatic Claisen rearrangement and intramolecular hydroaryloxylation were catalyzed by aluminum chloride. The second aromatic Claisen rearrangement step was also studied under thermal conditions to give mostly isomerized exocyclic compounds. The precursor endocyclic compounds were synthesized by thermal [3,3] sigmatropic rearrangement of the corresponding sulfide.Key words: alu

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13

T., S. S. P. N. S. Sanath Kumar, L. David Krupadanam G., Akshaya Kumar K., and Gourishankar Ch. "Benzofurans from acetophenones by Claisen rearrangement." Journal of Indian Chemical Society Vol. 87, Jul 2010 (2010): 887–89. https://doi.org/10.5281/zenodo.5799127.

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Department of Chemistry, Osmania University, Hyderabad-500 007, India Captain Srinivasa Murti Research Institute for Ayurveda and Siddha Drug Development, Arumbakkam, Chennai-600 106, India <em>E-mail :</em> drsanathkumar@ymail.com <em>E-mail </em>: kakshayak@hotmail.com, davidkrupa@hotmail.com Vasavi Engineering College, Hyderabad, India <em>Manuscript received 25 August 2009, revised 22 December 2009, accepted 28 January 2010</em> The condensation of acetophenones with propargylbromide in acetone-potassium carbonate medium yielded propargyloxyacetophenones which on thermal cyclisation leads

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14

Singha, Debabrata, Anwesha Bhattacharya, and Nilasish Pal. "Investigation on the thio-Claisen rearrangement of 2-[(4-aryloxy-2- butynyl)sulfanyl]thiophene." International Journal of Experimental Research and Review 27 (April 30, 2022): 53–58. http://dx.doi.org/10.52756/ijerr.2022.v27.006.

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2H-thiopyrano[3,2-c]coumarins have been regioselectively produced in 55-78% yield by the thermal [3,3] sigmatropic rearrangement led us to conduct research on the thio Claisen rearrangement of 2-[(4-aryloxy-2-butynyl)sulfanyl]thiophene. Six different cases using various 4-chlorobut-2-ynes were subjected to [3,3] sigmatropic rearrangement. The first cyclization in every cases were successful. The products formed contain allyl aryl ether moiety and as such there was scope for the second Claisen rearrangement with the products. The first Claisen product with Ar = 3,5-Me2C6H3 has been successfully

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15

Zhang, Guoting, Matthew D. Wodrich, and Nicolai Cramer. "Catalytic enantioselective reductive Eschenmoser-Claisen rearrangements." Science 383, no. 6681 (2024): 395–401. http://dx.doi.org/10.1126/science.adl3369.

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An important challenge in enantioselective catalysis is developing strategies for the precise synthesis of neighboring congested all-carbon quaternary stereocenters. The well-defined transition states of [3,3]-sigmatropic rearrangements and their underlying stereospecificity render them powerful tools for the synthesis of such arrays. However, this type of pericyclic reaction remains notoriously difficult to catalyze, especially in an enantioselective fashion. Herein, we describe an enantioselective reductive Eschenmoser-Claisen rearrangement catalyzed by chiral 1,3,2-diazaphospholene-hydrides

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16

Majumdar, K. C., and R. Islam. "Regioselective synthesis of biologically interesting pentacyclic polyheterocycles by sequential thio-Claisen and AlCl3 catalyzed oxy-Claisen rearrangement of 4-(4′-aryloxybut-2′-ynylthio)-1-phenyl-1,8-naphthyridin-2(1H)-one." Canadian Journal of Chemistry 84, no. 12 (2006): 1632–39. http://dx.doi.org/10.1139/v06-174.

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A number of 4-aryloxymethyl-6-phenyl-2H-thiopyrano[3,2-c][1,8]naphthyridin-5(6H)-ones were regio selectively synthesized in 82%–95% yields by the thermal Claisen rearrangement of 4-(4′-aryloxybut-2′-ynylthio)-1-phenyl-[1,8]naphthyridin-2(1H)-ones. These products were then subjected to a second Claisen rearrangement in the presence of a Lewis acid catalyst, anhyd. AlCl3, to give hitherto unreported pentacyclic heterocycles in 75%–90% yields. The same final products were also obtained in low yield upon refluxing 4-aryloxymethyl-6-phenyl-2H-thio pyrano-[3,2-c][1,8]naphthyridin-5(6H)-ones in N,N-d

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17

G., N. PATEL, and N. TRIVEDI K. "Abnormal Claisen Rearrangement of 3-Prenyloxyxanthone and 3-Prenyloxy-4-methylxanthone." Journal of Indian Chemical Society Vol. 65, Mar 1988 (1988): 192–93. https://doi.org/10.5281/zenodo.6035255.

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Department of Chemistry, Faculty of Science, M. B. University of Baroda, Baroda-390 002 <em>Manuscript received 29 July 1986, revised 9 September 1987, accepted 7 January 1988</em> Claisen rearrangement of 3-prenyloxyxanthone (1), when refluxed with dimethylaniline gave 4-(1,2-dimethylpropenyl)-3-hydroxyxanthone (2) and 1,1,2-trimethyl-1,2-dihydro-6<em>H</em>-furo[3,4-<em>b</em>]xanthen-9-one (3). 3-Prenyloxy-4- methylxanthone (4) on Claisen migration in dimethylaniline gave 2-(1,2- dimethylpropenyl)-3-hydroxy-4-methylxanthone (5). Also, Claisen rearrangement of 1 has been studied in

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18

Gajdošíková, Eva, Miroslava Martinková, Jozef Gonda, and Patrik Conka. "Microwave Accelerated Aza-Claisen Rearrangement." Molecules 13, no. 11 (2008): 2837–47. http://dx.doi.org/10.3390/molecules131102837.

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19

Craig, Donald, N. Paul King, Jörg T. Kley, and David M. Mountford. "Heteroaromatic Decarboxylative Claisen Rearrangement Reactions." Synthesis, no. 19 (2005): 3279–82. http://dx.doi.org/10.1055/s-2005-918448.

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20

Woerpel, K., and S. Calad. "Diastereoselective Silylene/Ireland-Claisen Rearrangement." Synfacts 2007, no. 5 (2007): 0519. http://dx.doi.org/10.1055/s-2007-968446.

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21

Miller, Steven P., and James P. Morken. "Catalytic Diastereoselective Reductive Claisen Rearrangement." Organic Letters 4, no. 16 (2002): 2743–45. http://dx.doi.org/10.1021/ol026273b.

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22

Majumdar, Krishna C., Safiul Alam, and Buddhadeb Chattopadhyay. "Catalysis of the Claisen rearrangement." Tetrahedron 64, no. 4 (2008): 597–643. http://dx.doi.org/10.1016/j.tet.2007.10.079.

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23

Ishihara, Jun, Yuki Watanabe, Noriko Koyama, Yukihiro Nishino, Keisuke Takahashi, and Susumi Hatakeyama. "Indium-mediated Reformatsky–Claisen rearrangement." Tetrahedron 67, no. 20 (2011): 3659–67. http://dx.doi.org/10.1016/j.tet.2011.03.079.

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24

Jackson, D. Y., J. W. Jacobs, R. Sugasawara, S. H. Reich, P. A. Bartlett, and Peter G. Schultz. "An antibody-catalyzed Claisen rearrangement." Journal of the American Chemical Society 110, no. 14 (1988): 4841–42. http://dx.doi.org/10.1021/ja00222a060.

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25

Tellier, Frédérique, Max Audouin, Monique Baudry, and Raymond Sauvêtre. "Claisen rearrangement of allylfluorovinyl ethers." Tetrahedron Letters 39, no. 28 (1998): 5041–44. http://dx.doi.org/10.1016/s0040-4039(98)01002-8.

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26

Ziegler, Frederick E. "The thermal, aliphatic Claisen rearrangement." Chemical Reviews 88, no. 8 (1988): 1423–52. http://dx.doi.org/10.1021/cr00090a001.

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27

Tellier, Frédérique, Max Audouin, Monique Baudry, and Raymond Sauvêtre. "Claisen rearrangement of allylfluorovinyl ethers." Journal of Fluorine Chemistry 94, no. 1 (1999): 27–36. http://dx.doi.org/10.1016/s0022-1139(98)00313-3.

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28

Ritter, Kurt. "Claisen rearrangement of organotin compounds." Tetrahedron Letters 31, no. 6 (1990): 869–72. http://dx.doi.org/10.1016/s0040-4039(00)94650-1.

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29

Krafft, Marie E., Sandra Jarrett, and Olivier A. Dasse. "A ligand assisted Claisen rearrangement." Tetrahedron Letters 34, no. 51 (1993): 8209–12. http://dx.doi.org/10.1016/s0040-4039(00)61392-8.

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30

Craig, Donald, N. Paul King, and David M. Mountford. "Silyl-modified Belluš–Claisen rearrangement." Chem. Commun., no. 10 (2007): 1077–79. http://dx.doi.org/10.1039/b614535c.

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31

Nelson, S., M. Geherty, and R. Dura. "Ruthenium-Catalyzed Asymmetric Claisen Rearrangement." Synfacts 2010, no. 11 (2010): 1270. http://dx.doi.org/10.1055/s-0030-1258795.

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32

Klyuchareva, E. V., E. V. Ershova, R. G. Nigmatullina, M. Yu Vozhdaeva, and E. A. Kantor. "On the Claisen rearrangement mechanism." Doklady Chemistry 424, no. 2 (2009): 52–55. http://dx.doi.org/10.1134/s0012500809020086.

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33

Ito, Hisanaka, and Takeo Taguchi. "ChemInform Abstract: Asymmetric Claisen Rearrangement." ChemInform 30, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199917315.

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34

Majumdar, K. C., and Trijit Bhattacharyya. "ChemInform Abstract: Aza-Claisen Rearrangement." ChemInform 33, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.200235279.

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35

Jain, Sanjay, Neelima Sinha, Dinesh K. Dikshit, and Nitya Anand. "Thio-Claisen rearrangement on pyroglutamates." Tetrahedron Letters 36, no. 46 (1995): 8467–68. http://dx.doi.org/10.1016/0040-4039(95)01731-v.

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36

Uli, Kazmaier. "Asymmetric syntheses of unsaturated amino acids and peptides via chelate-enolate Claisen rearrangements." Journal of Indian Chemical Society Vol. 76, Nov-Dec 1999 (1999): 631–39. https://doi.org/10.5281/zenodo.5861830.

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Organisch-Chemisches Institut der Universitat, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany <em>Manuscript received 6 September 1999</em> N-Protected amino acid allylic esters can easily be deprotonated by LDA at —78° and transmetallated by addition of metal salts. Upon warming up to room temperature, these enolates undergo Claisen rearrangements giving rise to unsaturated amino acids. Starting from chiral allylic alcohols, optically active amino acids are obtained. This chirality transfer can also be used for stereoselective peptide modifications. If tosylated peptide allylic

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37

Dudziński, Piotr, Wibke S. Husstedt, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5607–23. http://dx.doi.org/10.1039/d1ob00870f.

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[3,3]-Sigmatropic rearrangements based on different SF<sub>5</sub>-substituted allylic alcohols were investigated. The synthetic sequence developed for SF<sub>5</sub> compounds is also useful for CF<sub>3</sub> analogues and its application in Johnson–Claisen rearrangement.

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38

Tena, Alberto, Sofia Rangou, Sergey Shishatskiy, Volkan Filiz, and Volker Abetz. "Claisen thermally rearranged (CTR) polymers." Science Advances 2, no. 7 (2016): e1501859. http://dx.doi.org/10.1126/sciadv.1501859.

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Thermally rearranged (TR) polymers, which are considered the next-generation of membrane materials because of their excellent transport properties and high thermal and chemical stability, are proven to have significant drawbacks because of the high temperature required for the rearrangement and low degree of conversion during this process. We demonstrate that using a [3,3]-sigmatropic rearrangement, the temperature required for the rearrangement of a solid glassy polymer was reduced by 200°C. Conversions of functionalized polyimide to polybenzoxazole of more than 97% were achieved. These highl

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39

Gille, Annika, Julia Rehbein, and Martin Hiersemann. "Gosteli−Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements." Organic Letters 13, no. 8 (2011): 2122–25. http://dx.doi.org/10.1021/ol200558j.

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40

Domon, Daisuke, Kenshu Fujiwara, Natsumi Kawamura, Ryo Katoono, Hidetoshi Kawai, and Takanori Suzuki. "A New Variant of Fused Cyclic Ether Synthesis Based on Ireland-Claisen Rearrangement and RCM." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800718.

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A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement of a ( Z)-3-alkoxyprop-2-en-1-yl glycolate ester having a cyclic ether on the oxygen at C3 of the ( Z)-prop-2-en-1-yl group stereoselectively produced an anti-α,β-dialkoxyester which was successfully transformed to a fused bicyclic ether via a reaction sequence including RCM.

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41

Nadali, Samaneh, Ghasem Aghapour, and Zahra Rafieepour. "Efficient and selective iron-mediated reductive Claisen rearrangement of propargyloxyanthraquinones to anthrafurandiones in ionic liquids." Canadian Journal of Chemistry 95, no. 10 (2017): 1045–51. http://dx.doi.org/10.1139/cjc-2017-0328.

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An efficient and rapid method is described for the reductive Claisen rearrangement of different propargyloxyanthraquinones to anthra[1,2-b]furan-6,11-diones for first time using iron powder in a mixture of two ionic liquids, namely 1-methylimidazolium tetrafluoroborate [Hmim]BF4 and 1-benzyl-3-methylimidazolium chloride [Bzmim]Cl. The present method is able to execute single or double Claisen rearrangements of 1,4- or 1,5-bispropargyloxyanthraquinones selectively, so that the desired anthra(mono)furandiones or anthra(bis)furandiones are produced, respectively, as the major product.

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42

TSUNODA, Tetsuto, and Shô ITÔ. "Aza-Claisen Rearrangement. Conception and Evolution." Journal of Synthetic Organic Chemistry, Japan 52, no. 2 (1994): 113–20. http://dx.doi.org/10.5059/yukigoseikyokaishi.52.113.

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43

Okada, Yutaka, and Daisuke Imanari. "Claisen and Intermolecular Rearrangement of Cinnamyloxynaphthalenes." International Journal of Organic Chemistry 02, no. 01 (2012): 38–43. http://dx.doi.org/10.4236/ijoc.2012.21007.

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44

Kirsten, Martin, Julia Rehbein, Martin Hiersemann, and Thomas Strassner. "Organocatalytic Claisen Rearrangement: Theory and Experiment." Journal of Organic Chemistry 72, no. 11 (2007): 4001–11. http://dx.doi.org/10.1021/jo062455y.

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45

Ketcham, John M., Berenger Biannic, and Aaron Aponick. "The tandem intermolecular hydroalkoxylation/claisen rearrangement." Chem. Commun. 49, no. 39 (2013): 4157–59. http://dx.doi.org/10.1039/c2cc37166a.

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46

Sherry, Benjamin D., and F. Dean Toste. "Gold(I)-Catalyzed Propargyl Claisen Rearrangement." Journal of the American Chemical Society 126, no. 49 (2004): 15978–79. http://dx.doi.org/10.1021/ja044602k.

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47

Desimoni, Giovanni, Giuseppe Faita, Anna Gamba, Pier Paolo Righetti, Gianfranco Tacconi, and Lucio Toma. "Substituents effect on the claisen rearrangement." Tetrahedron 46, no. 6 (1990): 2165–78. http://dx.doi.org/10.1016/s0040-4020(01)89781-7.

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48

Vance, Robert L., Nelson G. Rondan, K. N. Houk, et al. "Transition structures for the Claisen rearrangement." Journal of the American Chemical Society 110, no. 7 (1988): 2314–15. http://dx.doi.org/10.1021/ja00215a059.

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49

Majumdar, Krishna C., Subhojit Ghosh, and Manish Ghosh. "The thio-Claisen rearrangement 1980–2001." Tetrahedron 59, no. 37 (2003): 7251–71. http://dx.doi.org/10.1016/s0040-4020(03)01023-8.

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50

Jacobsen, E., C. Uyeda, and A. Rötheli. "Chiral Guanidinium-Catalyzed Enantioselective Claisen Rearrangement." Synfacts 2011, no. 02 (2011): 0215. http://dx.doi.org/10.1055/s-0030-1259348.

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