Claisen Rearrangement Toward Cyclic Compound on Different Organic Synthesis Methods: Short Review

Authors

  • Rizki Rachmad Saputra Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Reny Rosalina Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Dimas Pramudita Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Oktavia Rahmi Wulandari Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Yuneta Yuneta Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Amanda Natania Gracia Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Tina Sugiyani Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia
  • Marsya Imelya Department of Chemistry, Faculty of Mathematics and Science, Universitas Palangka Raya, Palangka Raya 73112, Central Kalimantan, Indonesia

DOI:

https://doi.org/10.22437/chp.v7i2.26053

Keywords:

Cyclic compound synthesis, rearrangement reactions, Claisen Rearrangement, reaction mechanism

Abstract

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 reactions. An understanding of the mechanism and applications of this reaction might improve the ability to synthesize innovative and useful organic compounds in various fields of life sciences.

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References

Rao, S., & Prabhu, K. R. (2017). Gold-Catalyzed [2,3]-Sigmatropic Rearrangement: Reaction of Aryl Allyl Alcohols with Diazo Compounds. Organic Letters, 19(4), 846–849. https://doi.org/10.1021/acs.orglett.6b03836

Zhang, L., Hu, M., & Peng, B. (2019). [3,3]- and [5,5]-Sigmatropic Rearrangements of Aryl Sulfoxides Using An ‘Assembly/Deprotonation’ Technology. Synlett, 30(20), 2203–2208. https://doi.org/10.1055/s-0039-1690212

Lin, X., Tan, Z., Yang, W., Yang, W., Liu, X., & Feng, X. (2021). Chiral Cobalt(II) Complex Catalyzed Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Selenides with α-Diazo Pyrazoleamides. CCS Chemistry, 3(4), 1423–1433. https://doi.org/10.31635/ccschem.020.202000345

Zhu, G., Zhou, J., Liu, L., Li, X., Zhu, X., Lu, X., Zhou, J., & Ye, L. (2022). Catalystâ€Dependent Stereospecific [3,3]â€Sigmatropic Rearrangement of Sulfoxideâ€Ynamides: Divergent Synthesis of Chiral Mediumâ€Sized N , S â€Heterocycles. Angewandte Chemie, 134(28). https://doi.org/10.1002/ange.202204603

Gaykar, R. N., George, M., Guin, A., Bhattacharjee, S., & Biju, A. T. (2021). An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers. Organic Letters, 23(9), 3447–3452. https://doi.org/10.1021/acs.orglett.1c00911

Yorimitsu, H., & Perry, G. J. P. (2022). Sulfonium-aided coupling of aromatic rings via sigmatropic rearrangement. Proceedings of the Japan Academy, Series B, 98(4), PJA9804B-03. https://doi.org/10.2183/pjab.98.012

Smith, J. G. (2017). Organic Chemistry (Fifth Edition). MC Graw Hill.

Jukic, M., Sterk, D., & Casar, Z. (2012). Recent Advances in the Retro-Claisen Reaction and Its Synthetic Applications. Current Organic Synthesis, 9(4), 488–512. https://doi.org/10.2174/157017912802651438

Ji, Y.-B., Dong, F., Yu, M., Qin, L., & Liu, D. (2013). Optimization of Synthesis of Seleno-Sargassum fusiforme (Harv.) Setch. Polysaccharide by Response Surface Methodology, Its Characterization, and Antioxidant Activity. Journal of Chemistry, 2013, 1–9. https://doi.org/10.1155/2013/493524

Ripin, D. H. B., & Lewis, C. A. (2020). Rearrangements. In Practical Synthetic Organic Chemistry (pp. 377–423). Wiley. https://doi.org/10.1002/9781119448914.ch7

Ozaki, F., & Okada, Y. (2021). Microwave-assisted Claisen Rearrangement of 1-Allyloxy-4-hydroxybenzene in the Presence of Metal Salt. Current Microwave Chemistry, 8(1), 3–6. https://doi.org/10.2174/2213335607666210106094449

Kotha, S., & Meshram, M. (2018). Application of Claisen Rearrangement and Olefin Metathesis in Organic Synthesis. Chemistry – An Asian Journal, 13(14), 1758–1766. https://doi.org/10.1002/asia.201800613

Tsuda, M., Morita, T., & Nakamura, H. (2022). Synthesis of isoxazoloazaborines via gold(i)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade. Chemical Communications, 58(12), 1942–1945. https://doi.org/10.1039/D1CC07002A

Song, B. R., Ha, M. W., Kim, D., Park, C., Lee, K. W., & Paek, S.-M. (2019). Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement. Molecules, 24(24), 4597. https://doi.org/10.3390/molecules24244597

Jung, J., Kim, S., & Suh, Y. (2017). Advances in Azaâ€Claisenâ€Rearrangementâ€Induced Ringâ€Expansion Strategies. Asian Journal of Organic Chemistry, 6(9), 1117–1129. https://doi.org/10.1002/ajoc.201700202

Pramesti, I. N., & Okada, Y. (2022). Pengaruh Pelarut Terhadap Reaksi Penataan Ulang Claisen dan Siklisasi Senyawa Alil 1-Naftil Eter dengan Metode Microwave Assisted Organic Synthesis (MAOS). IJCA (Indonesian Journal of Chemical Analysis), 5(2), 86–94. https://doi.org/10.20885/ijca.vol5.iss2.art3

Nadali, S. , Khoshroo, A., & Aghapour, G. (2018). Efficient reductive Claisen rearrangement of prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones with iron powder in ionic liquids. Turkish Journal of Chemistry, 42(3), 883–895. https://doi.org/10.3906/kim-1711-49

Burns, J. M., Krenske, E. H., & McGeary, R. P. (2017). Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to (ortho-Tolyl)acetates. European Journal of Organic Chemistry, 2017(2), 252–256. https://doi.org/10.1002/ejoc.201601354

Khder, A. E. R. S., Ahmed, S. A., & Altass, H. M. (2016). Mesoporous metal(IV) phosphates as high performance acid catalysts for the synthesis of photochromic bis-naphthopyran via Claisen rearrangement. Reaction Kinetics, Mechanisms and Catalysis, 117(2), 745–759. https://doi.org/10.1007/s11144-015-0963-8

García-Lacuna, J., Domínguez, G., Blanco-Urgoiti, J., & Pérez-Castells, J. (2019). Synthesis of treprostinil: key Claisen rearrangement and catalytic Pauson–Khand reactions in continuous flow. Organic & Biomolecular Chemistry, 17(43), 9489–9501. https://doi.org/10.1039/C9OB02124H

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Published

2023-12-31

How to Cite

Saputra, R. R., Rosalina, R., Pramudita, D., Wulandari, O. R., Yuneta, Y., Gracia, A. N., Sugiyani, T., & Imelya, M. (2023). Claisen Rearrangement Toward Cyclic Compound on Different Organic Synthesis Methods: Short Review. Chempublish Journal, 7(2), 80-87. https://doi.org/10.22437/chp.v7i2.26053