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New Method for the Preparation of 2,3-Disubstituted 2,3-Dihydrothiazolo[3,2-a]pyrimidines

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Abstract

A new approach to the synthesis of 2,3-disubstituted 2,3-dihydrothiazolo[3,2-a]pyrimidines under microwave activation conditions has been developed. The method consists in the nucleophilic addition of methanol to 2-arylmethylidene derivatives of thiazolo[3,2-a]pyrimidine followed by intramolecular rearrangement to form 3,5-diaryl-2,3-dihydrothiazolo[3,2-a]pyrimidine-2,6-dicarboxylates.

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REFERENCES

  1. Cumming, J.G., McKenzie, C.L., Bowden, S.G., Campbell, D., Masters, D.J., Breed, J., and Jewsbury, P.J., Bioorg. Med. Chem. Lett., 2004, vol. 14, no. 21, pp. 5389–5394. https://doi.org/10.1016/j.bmcl.2004.08.007

    Article  CAS  Google Scholar 

  2. Abdel Moty, S.G., Hussein, M.A., Abdel Aziz, S.A., and Abou-Salim, M.A., Saudi Pharm. J., 2016, vol. 24, pp. 119–132. https://doi.org/10.1016/j.jsps.2013.12.016

    Article  Google Scholar 

  3. Keshari, A.K., Singh, A.K., and Saha, S., Mini-Rev. Med. Chem., 2017, vol. 17, p. 1488. https://doi.org/10.2174/1389557517666170216142113

    Article  CAS  Google Scholar 

  4. Hussein, M.A., Abdel Moty, S.G., Abdel Aziz, S.A., and Abou-Salim, M.A., Bull. Pharm. Sci., Assiut Univ., 2011, vol. 34, pp. 37–52. https://doi.org/10.21608/BFSA.2012.63216

    Article  CAS  Google Scholar 

  5. Sayed, H.H., Shamroukh, A.M., and Rashad, A.E., Acta Pharm., 2006, vol. 56, pp. 231–244.

    CAS  Google Scholar 

  6. Youssef, M.M. and Amin, M.A., Molecules, 2012, vol. 17, pp. 9652–9667. https://doi.org/10.3390/molecules17089652

    Article  CAS  Google Scholar 

  7. Maddila, S., Damu, G.L.V., Oseghe, E.O., Abafe, O.A., Venakata Rao, C., and Lavanya, P., J. Korean Chem. Soc., 2012, vol. 56, pp. 334–340. https://doi.org/10.5012/jkcs.2012.56.3.334

    Article  CAS  Google Scholar 

  8. Khalilpour, A., Asghari, S., and Pourshab, M., Chem. Biodivers., 2019, vol. 16, no. 5, e1800563. https://doi.org/10.1002/cbdv.201800563

    Article  CAS  Google Scholar 

  9. Izmest’ev, A.N., Vasileva, D.A., Melnikova, E.K., Kolotyrkina, N.G., Borisova, I.A., Kravchenko, A.N., and Gazieva, G.A., New J. Chem., 2019, vol. 43, pp. 1038–1052. https://doi.org/10.1039/C8NJ05058A

    Article  Google Scholar 

  10. Pansare, D.N., Shelke, R.N., and Shinde, D.B., J. Heterocycl. Chem., 2017, vol. 54, pp. 3077–3086. https://doi.org/10.1002/jhet.2919

    Article  CAS  Google Scholar 

  11. Nagarajaiah, H., Khazi, I.A.M., and Begum, N.S., J. Chem. Sci., 2015, vol. 127, no. 3, pp. 467–479. https://doi.org/10.1007/s12039-015-0797-y

    Article  CAS  Google Scholar 

  12. Zhao, D., Chen, C., Liu, H., Zheng, L., Tong, Y., Qu, D., and Han, S., Eur. J. Med. Chem., 2014, vol. 87, pp. 500–507. https://doi.org/10.1016/j.ejmech.2014.09.096

    Article  CAS  Google Scholar 

  13. Jin, C.-H., Jun, K.-Y., Lee, E., Kim, S., Kwon, Y., Kim, K., and Na, Y., Bioorg. Med. Chem., 2014, vol. 22, no. 17, pp. 4553–4565. https://doi.org/10.1016/j.bmc.2014.07.037

    Article  CAS  Google Scholar 

  14. Zhu, P., Fu, H., and Fang, H., Lett. Drug Des. Discov., 2017, vol. 14, no. 12, pp. 1382–1390. https://doi.org/10.2174/1570180814666170512123132

    Article  CAS  Google Scholar 

  15. Lebedyeva, I.O., Povstyanoy, M.V., Ryabitskii, A.B., and Povstyanoy, V.M., J. Heterocycl. Chem., 2010, vol. 47, no. 2, pp. 368–372. https://doi.org/10.1002/jhet.323

    Article  CAS  Google Scholar 

  16. Laurence, C. and Berthelot, M., Perspect. Drug Discov. Des., 2000, vol. 18, no. 1, pp. 39–60. https://doi.org/10.1023/A:1008743229409

    Article  CAS  Google Scholar 

  17. Singh, S., Schober, A., Gebinoga, M., and Gross, G.A., Tetrahedron Lett., 2011, vol. 52, no. 29, pp. 3814–3817. https://doi.org/10.1016/j.tetlet.2011.05.067

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

Measurements were performed using equipment of the Distributed Shared Facility Spectral and Analytical Center for Study of Structure, Composition, and Properties of Substances and Materials, Kazan Scientific Center, Russian Academy of Sciences.

Funding

This work was financially supported by the Kazan Scientific Center, Russian Academy of Sciences, to provide State Assignment in Scientific Area.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    A. S. Agarkov, A. A. Nefedova, A. S. Ovsyannikov, S. E. Solovieva &  I. S. Antipin

  2. Kazan Federal University, 420008, Kazan, Russia

    A. A. Kozhikhov

  3. Laboratory for Structural Analysis of Biomacromolecules, Kazan Scientific Center, Russian Academy of Sciences, 420111, Kazan, Russia

    D. R. Islamov

Authors
  1. A. S. Agarkov
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  2. A. A. Kozhikhov
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  3. A. A. Nefedova
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  4. A. S. Ovsyannikov
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  6. S. E. Solovieva
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Correspondence to A. S. Agarkov.

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Additional information

Translated by I. Kudryavtsev

The paper is presented to the thematic issue “Nitrogen heterocycles: synthesis, reactivity, and application.”

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Agarkov, A.S., Kozhikhov, A.A., Nefedova, A.A. et al. New Method for the Preparation of 2,3-Disubstituted 2,3-Dihydrothiazolo[3,2-a]pyrimidines. Dokl Chem 505, 177–183 (2022). https://doi.org/10.1134/S0012500822700070

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