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

Penulis

  • 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

Kata Kunci:

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

Abstrak

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.

Referensi

1. 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

2. 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

3. 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

4. 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

5. 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

6. 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

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

8. 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

9. 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

10. 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

11. 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

12. 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

13. 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

14. 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

15. 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

16. 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

17. 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

18. 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

19. 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

20. 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

Unduhan

Diterbitkan

2023-12-31 — Diperbaharui pada 2026-02-24

Versi

Terbitan

Vol 7 No 2 (2023): English

Bagian

Articles

Cara Mengutip

Claisen Rearrangement Toward Cyclic Compound on Different Organic Synthesis Methods: Short Review. (2026). Chempublish Journal, 7(2), 80-87. https://doi.org/10.22437/chp.v7i2.26053 (Original work published 2023)