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A novel approach to the synthesis of methimazole

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Abstract

The formation of the most widely used antithyroid drug in the world, 1-methyl-1H-imidazole-2(3H)-thione (methimazole or thiamazole), by the reduction of 4,5-dihydroxy-1-methylimidazolidine-2-thione (1-Me-DHIT) with 1-methylthiourea or by the reaction of 1-methylthiourea excess and glyoxal were studied. A new method for the synthesis of methimazole from available reagents, 1-Me-DHIT and 1-methylthiourea, was proposed.

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References

  1. E. B. Astwood, A. Bissell, A. M. Hughes, Endocrinology, 1945, 37, 456; DOI: https://doi.org/10.1210/endo-37-6-456.

    Article  CAS  PubMed  Google Scholar 

  2. R. G. Jones, J. Am. Chem. Soc., 1949, 71, 3994; DOI: https://doi.org/10.1021/ja01180a035.

    Article  CAS  Google Scholar 

  3. T. H. Brix, L. C. Lund, D. P. Henriksen, L. Folkestad, S. J. Bonnema, J. Hallas, L. Hegedüs, Lancet Diabetes Endocrinol., 2020, 8, 187; DOI: https://doi.org/10.1016/S2213-8587(20)30025-5.

    Article  CAS  PubMed  Google Scholar 

  4. A. Wohl, W. Marckwald, Ber. Deutsch. Chem. Ges., 1889, 22, 1353; DOI: https://doi.org/10.1002/cber.188902201280.

    Article  Google Scholar 

  5. W. Marckwald, Ber. Deutsch. Chem. Ges., 1892, 25, 2354; DOI: https://doi.org/10.1002/cber.18920250227.

    Article  Google Scholar 

  6. CN Pat. 107162983; Chem. Abstrs., 2017, 167, 496046.

  7. JP Pat. 2004143056; Chem. Abstrs., 2004, 140, 391282.

  8. CN Pat. 107602476; Chem. Abstrs., 2018, 168, 179370.

  9. CN Pat. 107353253; Chem. Abstrs., 2017, 168, 15260.

  10. CN Pat. 103214421; Chem. Abstrs., 2013, 159, 305531.

  11. L. J. Guziec, F. S. J. Guziec, J. Org. Chem., 1994, 59, 4691; DOI: https://doi.org/10.1021/jo00095a056.

    Article  CAS  Google Scholar 

  12. WO Pat. 2009074703; Chem. Abstrs., 2009, 151, 56849.

  13. CN Pat. 105541724; Chem. Abstrs., 2016, 164, 581893.

  14. CN Pat. 105523998; Chem. Abstrs., 2016, 164, 569873.

  15. KR Pat. 2021045045; Chem. Abstrs., 2021, 174, 929931.

  16. A. A. Galochkin, A. E. Pavlovskaya, V. V. Baranov, Yu. A. Strelenko, A. N. Kravchenko, Chem. Heterocycl. Compd., 2022, 58, 615; DOI: https://doi.org/10.1007/s10593-022-03134-2.

    Article  CAS  Google Scholar 

  17. V. V. Baranov, Yu. V. Nelyubina, A. N. Kravchenko, N. G. Kolotyrkina, K. A. Biriukova, Tetrahedron Lett., 2015, 56, 6085; DOI: https://doi.org/10.1016/j.tetlet.2015.09.071.

    Article  CAS  Google Scholar 

  18. V. V. Baranov, M. M. Antonova, V. A. Karnoukhova, A. N. Kravchenko, Tetrahedron Lett., 2017, 58, 2203; DOI: https://doi.org/10.1016/j.tetlet.2017.04.061.

    Article  CAS  Google Scholar 

  19. V. V. Baranov, M. M. Antonova, E. K. Melnikova, A. N. Kravchenko, Russ. Chem. Bull., 2020, 69, 401; DOI: https://doi.org/10.1007/s11172-020-2776-9.

    Article  CAS  Google Scholar 

  20. I. I. Ozturk, C. N. Banti, S. K. Hadjikakou, N. Panagiotou, A. J. Tasiopoulos, Inorg. Chim. Acta, 2019, 497, 119094; DOI: https://doi.org/10.1016/j.ica.2019.119094.

    Article  CAS  Google Scholar 

  21. K. Lafleur, D. Huang, T. Zhou, A. Caflisch, C. Nevado, J. Med. Chem., 2009, 52, 6433; DOI: https://doi.org/10.1021/jm9009444.

    Article  CAS  PubMed  Google Scholar 

  22. A. A. Isab, M. Fettouhi, M. R. Malik, S. Ali, A. Fazal, S. Ahmad, Russ. J. Coord. Chem., 2011, 37, 180; DOI: https://doi.org/10.1134/S1070328411030055.

    Article  CAS  Google Scholar 

  23. L. Kalichkina, D. Novikov, O. Kotelnikov, V. Malkov, A. Knyazev, Heterocycles, 2022, 104, 1954; DOI: https://doi.org/10.3987/COM-22-14731.

    Article  CAS  Google Scholar 

  24. C. J. Broan, A. R. Butler, J. Chem. Soc., Perkin. Trans. 2, 1991, 1501; DOI: https://doi.org/10.1039/P29910001501.

  25. L. Cao, A. Pizzi, Q. Zhang, H. Tian, H. Lei, X. Xi, G. Du, Eur. Polym. J., 2022, 162, 110915; DOI: https://doi.org/10.1016/j.eurpolymj.2021.110915.

    Article  CAS  Google Scholar 

  26. S. Deng, A. Pizzi, G. Du, J. Zhang, J. Zhang, J. Appl. Polym. Sci., 2014, 131, 41009; DOI: https://doi.org/10.1002/app.41009.

    Article  Google Scholar 

  27. N. Lavado, J. G. de la Concepción, M. Gallego, R. Babiano, P. Cintas, Org. Biomol. Chem., 2019, 17, 5826; DOI: https://doi.org/10.1039/C9OB01120J.

    Article  CAS  PubMed  Google Scholar 

  28. G. Baccolini, C. Boga, C. Delpivo, G. Micheletti, Tetrahedron Lett., 2011, 52, 1713; DOI: https://doi.org/10.1016/j.tetlet.011.02.002.

    Article  CAS  Google Scholar 

  29. K. T. Potts, R. Ehlinger, S. Kanemasa, J. Org. Chem., 1980, 45, 2474; DOI: https://doi.org/10.1021/jo01300a042.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. V. Baranov, A. A. Galochkin & A. N. Kravchenko

Authors
  1. V. V. Baranov
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  2. A. A. Galochkin
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  3. A. N. Kravchenko
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Corresponding author

Correspondence to V. V. Baranov.

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The authors declare no competing interests.

Additional information

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1946–1949, August, 2023.

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Baranov, V.V., Galochkin, A.A. & Kravchenko, A.N. A novel approach to the synthesis of methimazole. Russ Chem Bull 72, 1946–1949 (2023). https://doi.org/10.1007/s11172-023-3983-y

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  • DOI: https://doi.org/10.1007/s11172-023-3983-y

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