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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 8, pp 759–761 | Cite as

Open image in new window Synthesis of 5-hydroxyfuran-2(5H)-one derivatives (microreview)

  • Sergey V. Fedoseev
  • Mikhail Yu. Belikov
Article
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In this microreview, we describe methods for the synthesis of 5-hydroxyfuran-2(5H)-one derivatives, which have been published over the last 5 years. The main routes for the preparation of 5-hydroxyfuran-2(5H)-one derivatives include transformations of 2-oxocarboxylic acids, formylation or carboxylation of functionalized aromatic (heterocyclic) compounds, as well as synthetic modifications of furan derivatives.

Notes

This work was financed by a grant from the President of the Russian Federation for support of young scientists in Russia (MK-5982.2018.3).

References

  1. 1.
    Parker, A. N.; Lock, M. J.; Hutchison, J. M. Tetrahedron Lett. 2013, 54, 5322.CrossRefGoogle Scholar
  2. 2.
    Urosa, A.; Marcos, I. S.; Díez, D.; Lithgow, A.; Plata, G. B.; Padrón, J. M.; Basabe, P. Mar. Drugs 2015, 13, 2407.CrossRefPubMedCentralGoogle Scholar
  3. 3.
    Boukouvalas, J.; Albert, V. Heterocycles 2014, 88, 939.CrossRefGoogle Scholar
  4. 4.
    Deore, P. S.; Argade, N. P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2014, 53, 1140.Google Scholar
  5. 5.
    (a) Pereira, U. A.; Moreira, T. A.; Barbosa, L. C. A.; Maltha, C. R. A.; Bomfim, I. S.; Maranhão, S. S.; Moraes, M. O.; Pessoa, C.; Barros-Nepomuceno, F. W. A. MedChemComm 2016, 7, 345. (b) Beck, D. E.; Agama, K.; Marchand, C.; Chergui, A.; Pommier, Y.; Cushman, M. J. Med. Chem. 2014, 57, 1495.Google Scholar
  6. 6.
    (a) Urosa, A.; Marcos, I. S.; Díez, D.; Plata, G. B.; Padrón, J. M.; Basabe, P. Mol. Diversity 2016, 20, 369. (b) Gil-Mesón, A.; Roncero, A. M.; Tobal, I. E.; Basabe, P.; Díez, D.; Mollinedo, F.; Marcos, I. S. Molecules 2016, 21, 47. (c) Beck, D. E.; Lv, W.; Abdelmalak, M.; Plescia, C. B.; Agama, K.; Marchand, C.; Pommier, Y.; Cushman, M. Bioorg. Med. Chem. 2016, 24, 1469. (d) Urosa, A.; Marcos, I. S.; Díez, D.; Lithgow, A.; Plata, G. B.; Padrón, J. M.; Basabe, P. Mar. Drugs 2015, 13, 2407. (e) Beck, D. E.; Abdelmalak, M.; Lv W.; Narasimha, R. P. V.; Tender, G. S.; O'Neill, E.; Agama, K.; Marchand, C.; Pommier, Y.; Cushman, M. J. Med. Chem. 2015, 58, 3997.Google Scholar
  7. 7.
    (a) Yamawaki, K.; Yokoo, K.; Sato, A.; Kusano, H.; Aoki, T.; Liao, X.; Pearson, N. D.; Israil, P.; Reema, T. JP Patent 2015221788. (b) Yamawaki, K.; Kusano, H. WO Patent 2014104148. (c) Hubschwerlen, C.; Kaegi-Egger, V.; Rueedi, G.; Zumbrunn, C. WO Patent 2014181266. (d) Liao, X.; Pearson, N. D.; Pendrak, I.; Thalgi, R.; Yamawaki, K.; Yokoo, K.; Sato, J.; Kusano, H.; Aoki, T. WO Patent 2014068388.Google Scholar
  8. 8.
    Bhattacharya, A. K.; Chand, H. R.; John, J.; Deshpande, M. V. Eur. J. Med. Chem. 2015, 94, 1.CrossRefGoogle Scholar
  9. 9.
    Müller, D. S.; Untiedt, N. L.; Dieskau, A. P.; Lackner, G. L.; Overman, L. E. J. Am. Chem. Soc. 2015, 137, 660.CrossRefGoogle Scholar
  10. 10.
    Mao, W.; Zhu, C. Chem. Commun. 2016, 52, 5269.CrossRefGoogle Scholar
  11. 11.
    Qiang, X.; Lia, Y.; Yang, X.; Luo, L.; Xu, R.; Zheng, Y.; Cao, Z.; Tan, Z.; Deng, Y. Bioorg. Med. Chem. Lett. 2017, 27, 718.CrossRefGoogle Scholar
  12. 12.
    Dwight, S. J.; Levin, S. Org. Lett. 2016, 18, 5316.CrossRefGoogle Scholar
  13. 13.
    (a) He, Z.; Fang, F.; Lv, J.; Zhang, J. Tetrahedron Lett. 2017, 58, 1034. (b) Lyu, J.; Zhang, J.; Fang, F.; Guo, Y.; He, Z.; Cao, L.; Hu, H.; Li, X.; Xu, K. CN Patent 106565644.Google Scholar
  14. 14.
    (a) Bolchi, C.; Roda, G.; Pallavicini, M. Synth. Commun. 2018, 48, 85. (b) Wang, C.; Chen, Z.; Wang, C. CN Patent 106748950. (c) Defrance, T.; Septavaux, J.; Nuel, D. WO Patent 2017076738. (d) Chen, Y.; Tsao, K.; De Francesco, E.; Keillor, J. W. J. Org. Chem. 2015, 80, 12182.Google Scholar
  15. 15.
    (a) Lam, B.; Arikawa, Y.; Cramlett, J.; Dong, Q.; de Jong, R.; Feher, V.; Grimshaw, C. E.; Farrell, P. J.; Hoffman, I. D.; Jennings, A.; Jones, B.; Matuszkiewicz, J.; Miura, J.; Miyake, H.; Srinivasa, R. N.; Shi, L.; Takahashi, M.; Taylor, E.; Wyrick, C.; Yano, J.; Zalevsky, J.; Nie, Z. Bioorg. Med. Chem. Lett. 2016, 26, 5947. (b) Chen, R.; Ichibakase, T.; Ma, C.; Matthews, C.; Motoyoshi, H.; O'Bryan, C.; Yaji, K.; Yoshikawa, N. WO Patent 2016097862. (c) Thoma, G.; Buehlmayer, P.; Van, E. M.; Smith, A. B. WO Patent 2014027300.Google Scholar
  16. 16.
    (a) Saidachary, G.; China Raju, B. Helv. Chim. Acta 2016, 99, 425. (b) Schünemann, K.; Furkert, D. P.; Choi, E. C.; Connelly, S.; Fraser, J. D.; Sperry, J.; Brimble, M. A. Org. Biomol. Chem. 2014, 12, 905.Google Scholar
  17. 17.
    Basak, S.; Mandal, S.; Mal, D. Tetrahedron 2018, 74, 96.CrossRefGoogle Scholar
  18. 18.
    Lin, Y.; Zhu, L.; Lan, Y.; Rao, Y. Chem.–Eur. J. 2015, 21, 14937.CrossRefGoogle Scholar
  19. 19.
    Hong, X.; Wang, H.; Liu, B.; Xu, B. Chem. Commun. 2014, 50, 14129.CrossRefGoogle Scholar
  20. 20.
    (a) Sk, M. R.; Chakraborty, S.; Mal, D. Synth. Commun. 2018, 48, 309. (b) Cushman, M. S.; Beck, D. E.; Pomhier, Y. WO Patent 2017160898. (c) Beck, D. E.; Narasimha, R. P. V.; Lv, W., Abdelmalak, M.; Tender, G. S.; Lopez, S.; Agama, K.; Marchand, C.; Pommier, Y.; Cushman, M. J. Med. Chem. 2016, 59, 3840. (d) Roy, J.; Mal, T.; Jana S.; Mal, D. Beilstein J. Org. Chem. 2016, 12, 531. (e) Mal, D.; Roy, J. Org. Biomol. Chem. 2015, 13, 6344. (f) Nicolaou, K. C.; Lu, M.; Mandal, D.; Gangwar, S.; Chowdari, N. S.; Poudel, Y. B. WO Patent 2015023879. (g) Jiao, J.; Shafer, J. A. WO Patent 2015095052. (h) Nandakumar, M.; Sankar, E.; Mohanakrishnan, A. K. Synlett 2014, 509.Google Scholar
  21. 21.
    Suneja, A.; Bisai, V.; Singh, V. K. J. Org. Chem. 2016, 81, 4779.CrossRefGoogle Scholar
  22. 22.
    (a) Pošta, M.; Soós, V.; Beier, P. Tetrahedron 2016, 72, 3809. (b) Boukouvalas, J.; Albert, V. Heterocycles 2014, 88, 939. (c) Deore, P. S.; Batwal, R. U.; Argade, N. P. Synthesis 2015, 485.Google Scholar
  23. 23.
    Salles, A. G., Jr.; Zarra, S.; Turner, R. M.; Nitschke, J. R. J. Am. Chem. Soc. 2013, 135, 19143.CrossRefGoogle Scholar
  24. 24.
    (a) Zhong, Z.; Zhao, G.; Xu, D.; Dong, B.; Song, D.; Xie, X.; She, X. Chem.–Asian J. 2016, 11, 1542. (b) Gil-Mesón, A; Roncero, A. M.; Tobal, I. E.; Basabe, P.; Díez, D.; Mollinedo, F.; Marcos, I. S. Molecules 2016, 21, 47. (c) Zhang, Y.; Wang, W.; Li, S. Asian J. Chem. 2015, 27, 111. (d) Xu, H.; Tang, H.; Feng, H.; Li, Y. ChemMedChem 2014, 9, 290.Google Scholar
  25. 25.
    Costas, T.; Costas-Lago, V. C.; Vila, N.; Besada, P.; Cano, E.; Terán, C. Eur. J. Med. Chem. 2015, 94, 113.CrossRefGoogle Scholar
  26. 26.
    Nguyen, T. V. Q.; Rodríguez-Santamaría, J. A.; Yoo, W.-J.; Kobayashi, S. Green Chem. 2017, 19, 2501.CrossRefGoogle Scholar
  27. 27.
    Hua, Y.; Asgari, P.; Dakarapu, U. S.; Jeon, J. Chem. Commun. 2015, 51, 3778.CrossRefGoogle Scholar
  28. 28.
    Fedoseev, S. V.; Ershov, O. V.; Lipin, K. V.; Belikov, M. Yu. RSC Adv. 2016, 6, 10597.CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia

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