Skip to main content
Log in

Tetrahydro-4H-thiopyran-4-one in multicomponent reactions (microreview)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This paper summarizes multicomponent reactions with the participation of tetrahydro-4H-thiopyran-4-one, mainly resulting in the formation of sulfur- and nitrogen-containing polyheterocyclic systems, that have been published over the last 7 years.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Haugland, M. M.; Anderson, E. A.; Lovett, J. E. Electron Paramagn. Reson. 2017, 25, 1.

    Google Scholar 

  2. (a) Rule, N. G.; Kung, T.-M. US Patent 5039585. (b) Lenhard, J. R.; Shukla, D. US Patent 7471437.

  3. (a) Rentner, J.; Kljajic, M.; Offner, L.; Breinbauer, R. Tetrahedron 2014, 70, 8983. (b) Ward, D. E. Chem. Commun. 2011, 47, 11375. (c) Becerril-Jiménez, F.; Ward, D. E. Org. Lett. 2012, 14, 1648.

  4. (a) Zhou, D.-Y.; Zhao, S.-Q.; Du, Z.-Y.; Zheng, X.-I.; Zhang, K. Oncol. Lett. 2016, 11, 4160. (b) Lei, F.; Sun, C.; Xu, S.; Wang, Q.; OuYang, Y.; Chen, C.; Xia, H.; Wang, L.; Zheng, P.; Zhu, W. Eur. J. Med. Chem. 2016, 116, 27. (c) Hegab, M. I.; Morsy, E. M. H.; Abd El-Mageed, A. E.; Ali, M. M.; El-Senousy, W. M.; Tolan, H. E. M.; Gad, F. A.; Abdel-Megeid, F. M. E. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1901. (d) Gable, J. E.; Acker, T. M.; Craik, C. S. Chem. Rev. 2014, 114, 11382. (e) Pasha, G. F.; Asghari, S.; Tajbakhsh, M.; Mohseni, M. Res. Chem. Intermed. 2017, 43, 7291.

  5. (а) Ward, D. E.; Kazemeini, A. J. Org. Chem. 2012, 77, 10789. (b) Tsakos, M.; Kokotos, C. G. Tetrahedron 2013, 69, 10199. (c) Mo, L.; Tang, H.; Yao, Z.-J. Tetrahedron 2013, 69, 6897. (d) Guan, Z.; Luo, Y.; Zhang, B.-Q.; Heinen, K.; Yang, D.-C.; He, Y.-H. Tetrahedron: Asymmetry 2014, 25, 802. (e) Mostinski, Y.; Valerio, V.; Lankri, D.; Tsvelikhovsky, D. J. Org. Chem. 2015, 80, 10464. (f) Yang, C.; Zhang, K.; Wu, Z.; Yao, H.; Lin, A. Org. Lett. 2016, 18, 5332. (g) Stivanin, M. L.; Duarte, M.; Sartori, C.; Capreti, N. M. R.; Angolini C. F. F.; Jurberg, I. D. J. Org. Chem. 2017, 82, 10319. (h) Borst, M. L. G.; Ouairy, C. M. J.; Fokkema, S. C.; Cecchi, A.; Kerckhoffs, J. M. C. A.; de Boer, V. L.; van den Boogaard, P. J.; Bus, R. F.; Ebens, R.; van der Hulst, R.; Knol, J.; Libbers, R.; Lion, Z. M.; Settels, B. W.; de Wever, E.; Attia, K. A.; Sinnema, P.-J.; de Gooijer, J. M.; Harkema, K.; Hazewinkel, M.; Snijder, S.; Pouwer, K. ACS Comb. Sci. 2018, 20, 335.

  6. (a) Ordóñez, M.; Sayago, F. J.; Cativiela, C. Tetrahedron 2012, 68, 6369. (b) van Walree, C. A.; Lutz, M.; Spek, A. L.; Jenneskens, L. W.; Havenith, R. W. A. J. Mol. Struct. 2013, 1036, 115. (c) Allwood, D. M.; Blakemore, D. C.; Brown, A. D.; Ley, S. V. J. Org. Chem. 2014, 79, 328. (d) Ghashang, M.; Mansoor, S. S.; Shafiee, M. R. M.; Kargar, M.; Biregan, M. N.; Azimi, F.; Taghrir, H. J. Sulfur Chem. 2016, 37, 377. (e) Nomiyama, S; Ogura, T.; Ishida, H.; Aoki, K.; Tsuchimoto, T. J. Org. Chem. 2017, 82, 5178.

  7. (a) Guan, Z.; Song, J.; Xue, Y.; Yang, D.-C.; He, Y.-H. J. Mol. Catal. B: Enzym. 2015, 111, 16. (b) Abaee, M. S.; Mojtahedi, M. M.; Akbari, A.; Mehraki, E.; Mesbah, A. W.; Harms, K. J. Heterocycl. Chem. 2012, 49, 1346.

  8. Wang, S.-L.; Liu, Y.-P.; Xu, B.-H.; Wang, X.-H.; Jiang, B.; Tu, S.-J. Tetrahedron 2011, 67, 9417.

    Article  CAS  Google Scholar 

  9. Jiang, B.; Xue, L.-Y.; Wang, X.-H.; Tu, M.-S.; Liu, Y.-P.; Tu, S.-J. Tetrahedron Lett. 2012, 53, 1261.

    Article  CAS  Google Scholar 

  10. Sha, Q.; Arman, H.; Doyle, M. P. Org. Lett. 2015, 17, 3876.

    Article  CAS  PubMed  Google Scholar 

  11. (a) Deng, Y.; Liu, L.; Sarkisian, R. G.; Wheeler, K.; Wang, H.; Xu, Z. Angew. Chem., Int. Ed. 2013, 52, 3663. (b) Deng, Y.; Kumar, S.; Wang, H. Chem. Commun. 2014, 50, 4272. (c) Eftekhari-Sis, B.; Zirak, M. Chem. Rev. 2015, 115, 151. (d) Deng, Y.; Karunaratne, C. V.; Csatary, E.; Tierney, D. L.; Wheeler, K.; Wang, H. J. Org. Chem. 2015, 80, 7984. (e) Deng, Y.; Kumar, S.; Wheeler, K.; Wang, H. Chem.–Eur. J. 2015, 21, 7874.

  12. Jiang. B.; Zhang, T.-S.; Fu, R.; Hao, W.-J.; Wang, S.-L.; Tu, S.-J. Tetrahedron 2016, 72, 5652.

  13. (a) Mojtahedi, M. M.; Pourabdi, L.; Abaee, M. S.; Jami, H.; Dini, M.; Halvagar, M. R. Tetrahedron 2016, 72, 1699. (b) Abaee, S. M.; Forghani, S.; Mojtahedi, M. M.; Harms, K. J. Sulfur Chem. 2016, 37, 683.

  14. Pourabdi, L.; Osati, F.; Mojtahedi, M. M.; Abaee, S. M. J. Sulfur Chem. 2017, 38, 34.

    Article  CAS  Google Scholar 

  15. Ashitha, K. T.; Kumar, V. P.; Salfeena, C. T. F.; Sasidhar, B. S. J. Org. Chem. 2018, 83, 113.

    Article  CAS  PubMed  Google Scholar 

  16. Santra, S.; Andreana, P. R. J. Org. Chem. 2011, 76, 2261.

    Article  CAS  PubMed  Google Scholar 

  17. Abaee, M. S.; Cheraghi, S. ARKIVOC 2014, (iv), 1.

  18. (a) Huang, Y.; Dömling, A. Mol. Diversity 2011, 11, 3. (b) Hempel, J. E.; Cadar, A. G.; Hong, C. C. Bioorg. Med. Chem. Lett. 2016, 26, 1947. (c) Rai, G.; Vyjayanti, V. N.; Dorjsuren, D.; Simeonov, A.; Jadhav, A.; Wilson, D. M.; Maloney, D. J. J. Med. Chem. 2012, 55, 3101.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Larisa А. Baeva.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1108–1110

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baeva, L.А. Tetrahydro-4H-thiopyran-4-one in multicomponent reactions (microreview). Chem Heterocycl Comp 54, 1108–1110 (2018). https://doi.org/10.1007/s10593-019-02399-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02399-4

Navigation