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Stereoselective synthesis of tetrahydropyrimidin-2(1H)-ones (minireview)

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Chemistry of Heterocyclic Compounds Aims and scope

We provide a generalized overview of stereoselective synthetic strategies used for the preparation of tetrahydropyrimidin-2(1H)-one derivatives, illustrated by the most relevant examples published between years 2012 and 2022. The known methods can be divided into two main groups: intramolecular and intermolecular cyclization of unsaturated acyclic amides/ureas, as well as syntheses on the basis of cyclic precursors.

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References

  1. Smolobochkin, A. V.; Gazizov, A. S.; Burilov, A. R.; Pudovik, M. A.; Sinyashin, O. G. Russ. Chem. Rev. 2021, 90, 395.

    Article  CAS  Google Scholar 

  2. Hurst, M.; Faulds, D. Drugs 2000, 60, 1371.

    Article  CAS  PubMed  Google Scholar 

  3. Cvetkovic, R. S.; Goa, K. L. Drugs 2003, 63, 769.

    Article  CAS  PubMed  Google Scholar 

  4. Chandwani, A.; Shuter, J. Ther. Clin. Risk Manage. 2008, 4, 1023.

    Article  CAS  Google Scholar 

  5. Jančić, A. M.; Katanić Stanković, J. S.; Srećković, N.; Mihailović, V.; Komatina, D. I.; Stevanović, D. J. Organomet. Chem. 2022, 967, 122335.

    Article  Google Scholar 

  6. Sudhamani, H.; Thaslim Basha, S. K.; Adam, S.; Madhusudhana, S.; Usha Rani, A.; Naga Raju, C. Res. Chem. Intermed. 2017, 43, 103.

    Article  CAS  Google Scholar 

  7. Yang, W.; Wang, Y.; Lai, A.; Clark, C. G.; Corte, J. R.; Fang, T.; Gilligan, P. J.; Jeon, Y.; Pabbisetty, K. B.; Rampulla, R. A.; Mathur, A.; Kaspady, M.; Neithnadka, P. R.; Arumugam, A.; Raju, S.; Rossi, K. A.; Myers, J. E.; Sheriff, S.; Lou, Z.; Zheng, J. J.; Chacko, S. A.; Bozarth, J. M.; Wu, Y.; Crain, E. J.; Wong, P. C.; Seiffert, D. A.; Luettgen, J. M.; Lam, P. Y. S.; Wexler, R. R.; Ewing, W. R. J. Med. Chem. 2020, 63, 7226.

    Article  CAS  PubMed  Google Scholar 

  8. Wu, J.; Wang, C.; Häberli, C.; White, K. L.; Shackleford, D. M.; Chen, G.; Dong, Y.; Charman, S. A.; Keiser, J.; Vennerstrom, J. L. Bioorg. Med. Chem. Lett. 2018, 28, 3648.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Fortin, S.; Wei, L.; Moreau, E.; Lacroix, J.; Côté, M.-F.; Petitclerc, E.; Kotra, L. P.; C.-Gaudreault, R. J. Med. Chem. 2011, 54, 4559.

  10. Yukawa, T.; Nakada, Y.; Sakauchi, N.; Kamei, T.; Yamada, M.; Ohba, Y.; Fujimori, I.; Ueno, H.; Takiguchi, M.; Kuno, M.; Kamo, I.; Nakagawa, H.; Fujioka, Y.; Igari, T.; Ishichi, Y.; Tsukamoto, T. Bioorg. Med. Chem. 2016, 24, 3716.

    Article  CAS  PubMed  Google Scholar 

  11. Fujimoto, T.; Imaeda, Y.; Konishi, N.; Hiroe, K.; Kawamura, M.; Textor, G. P.; Aertgeerts, K.; Kubo, K. J. Med. Chem. 2010, 53, 3517.

    Article  CAS  PubMed  Google Scholar 

  12. Wu, T.; Cheng, J.; Chen, P.; Liu, G. ChemComm 2013, 49, 8707.

    CAS  Google Scholar 

  13. Bretzke, S.; Scheeff, S.; Vollmeyer, F.; Eberhagen, F.; Rominger, F.; Menche, D. Beilstein J. Org. Chem. 2016, 12, 1111.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Morgen, M.; Bretzke, S.; Li, P.; Menche, D. Org. Lett. 2010, 12, 4494.

    Article  CAS  PubMed  Google Scholar 

  15. Wu, J.; Zhu, K.-C.; Yuan, P.-W.; Panek, J. S. Org. Lett. 2012, 14, 3624.

    Article  CAS  PubMed  Google Scholar 

  16. Nishikawa, Y.; Kimura, S.; Kato, Y.; Yamazaki, N.; Hara, O. Org. Lett. 2015, 17, 888.

    Article  CAS  PubMed  Google Scholar 

  17. Struble, T. J.; Lankswert, H. M.; Pink, M.; Johnston, J. N. ACS Catal. 2018, 8, 11926.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Khan, I.; Shah, B. H.; Zhao, C.; Xu, F.; Zhang, Y. J. Org. Lett. 2019, 21, 9452.

    Article  CAS  PubMed  Google Scholar 

  19. Berthold, D.; Geissler, A. G. A.; Giofré, S.; Breit, B. Angew. Chem. 2019, 131, 10099.

    Article  Google Scholar 

  20. Geissler, A. G. A.; Riesterer, J. R.; Breit, B. Org. Lett. 2021, 23, 9168.

    Article  CAS  PubMed  Google Scholar 

  21. Lillo, V. J.; Saá, J. M. Chem.–Eur. J. 2016, 22, 17182.

  22. Sukach, V. A.; Resetnic, A. A.; Tkachuk, V. M.; Lin, Z.; Kortz, U.; Vovk, M. V.; Röschenthaler, G.-V. Eur. J. Org. Chem. 2015, 1290.

  23. Melnykov, S. V.; Pataman, A. S.; Dmytriv, Y. V.; Shishkina, S. V.; Vovk, M. V.; Sukach, V. A. Beilstein J. Org. Chem. 2017, 13, 2617.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Feng, G.-S.; Shi, L.; Meng, F.-J.; Chen, M.-W.; Zhou, Y.-G. Org. Lett. 2018, 20, 6415.

    Article  CAS  PubMed  Google Scholar 

  25. Feng, G.-S.; Chen, M.-W.; Shi, L.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2018, 57, 5853.

  26. Dao Thi, H.; Danneels, B.; Desmet, T.; Van Hecke, K.; Van Nguyen, T.; D'hooghe, M. Asian J. Org. Chem. 2016, 5, 1480.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 8 Akademika Arbuzova St, Kazan, 420088, Russia

    Andrey V. Smolobochkin & Almir S. Gazizov

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  1. Andrey V. Smolobochkin
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  2. Almir S. Gazizov
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Correspondence to Andrey V. Smolobochkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 237–239

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Smolobochkin, A.V., Gazizov, A.S. Stereoselective synthesis of tetrahydropyrimidin-2(1H)-ones (minireview). Chem Heterocycl Comp 59, 237–239 (2023). https://doi.org/10.1007/s10593-023-03185-z

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