Skip to main content
Log in

Synthesis of 6H-1,2-oxazin-6-ones (microreview)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The microreview is devoted to the methods of synthesis of 6H-1,2-oxazin-6-ones published after 1999 and covers both universal and specific methods for the preparation of this class of compounds.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) Abubshait, S. A.; Kassab, R. R.; Al-Shehri, A. H.; Abubshait, H. A. J. Saudi Chem. Soc. 2011, 15, 59. (b) Gonçalves, D. S.; Silva, M. J. V.; Souza, T. F.; Jacomini, A. P.; Back, D. F.; Basso, E. A.; Moura, S.; Rosa, F. A. Synthesis 2016, 3042.

  2. Stevenson, T. M. US Patent 20120329787A1.

  3. Abd El-Ghaffar, N. F.; Mohamed, M. Kh.; Kadah, M. S.; Radwan, A. M.; Said, G. H.; Abd el Al, S. N. J. Chem. Pharm. Res. 2011, 3, 248.

  4. Barker, M.; Clackers, M.; Demaine, D. A.; Humphreys, D.; Johnston, M. J.; Jones, H. T.; Pacquet, F.; Pritchard, J. M.; Salter, M.; Shanahan, S. E.; Scone P. A.; Vinader, V. M.; Uings, I.; McLay, I. M.; Macdonald, S. J. F. J. Med. Chem. 2005, 48, 4507.

  5. Rios, M. Y.; Navarro, V.; Ramírez-Cisneros, M. Á.; Salazar-Rios, E. J. Nat. Prod. 2017, 80, 3112.

  6. Csende, F.; Stájer, G. Heterocycles 2000, 53, 1379.

  7. (a) Mourad, A. K.; Makhlouf, A. A.; Soliman, A. Y.; Mohamed, S. A. J. Chem. Res. 2020, 44, 31. (b) El-Shenawy, A. L. Chem. Pap. 2004, 58, 205. (c) Abo-Bakr, A. M.; Hassan, M. A.; Temirek, H. H.; Mosallam, A. M. Orient. J. Chem. 2012, 28, 1567.

  8. Yuossef, M. S. K.; Fahmy, A. F.; Halim, M. S. A.; Hassan, M. A.; Sauer, J. Org. Prep. Proced. Int. 2005, 37, 247.

  9. (a) Rudenko, D. A.; Shavrina, T. V.; Shurov, S. N.; Zykova, S. S. Pharm. Chem. J. 2014, 48, 100. [Khim. Farm. Zh. 2014, 48(2), 32.] (b) Rudenko, D. A.; Slepukhin, P. A.; Karmanov, V. I.; Shurov, S. N.; Vakhrin, M. I.; Shchurov, Yu. A. Chem. Heterocycl. Compd. 2013, 48, 1539. [Khim. Geterotsikl. Soedin. 2012, 1651.]

  10. Bildirici, I.; Şener, A.; Tozlu, I. Med. Chem. Res. 2007, 16, 418.

  11. Sakthidharan, C. P.; Sampathkumar, N. Heterocycl. Lett. 2011, 1, 43.

  12. Faidallah, H. M.; Khan, K. A.; Makki, M. S. I. J. Chin. Chem. Soc. 2011, 58, 191.

  13. Zhang, Y.; Wang, Q.; Yu, H.; Huang, Y. Org. Biomol. Chem. 2014, 12, 8844.

  14. (a) Jing, K.; Yao. J.-P.; Li, Z.-Y.; Li, Q.-L.; Lin, H.-S.; Wang. G.-W. J. Org. Chem. 2017, 82, 12715. a Jing, K.; Cui, P.-C.; Wang, G.-W. Chem. Commun. 2019, 55, 12551.

  15. Xu, Y.; Hu, W.; Tang, X.; Zhao, J.; Wu, W.; Jiang, H. Chem. Commun. 2015, 51, 6843.

  16. Suchand, B.; Satyanarayana, G. Eur. J. Org. Chem. 2018, 2233.

  17. Chun, T. G.; Kim, K. S.; Lee, S.; Jeong, T.-S.; Lee, H.-Y.; Kim, Y. H.; Lee, W. S. Synth. Commun. 2004, 34, 1301.

  18. Dang, T. T.; Albrecht, U.; Langer, P. Synthesis 2006, 2515.

  19. Pathak, S.; Debnath, K.; Hossain, Sk. T.; Mukherjee, S. K.; Pramanik, A. Tetrahedron Lett. 2013, 54, 3137.

  20. (a) Wang, X.; Li, G.; Zhang, X.; Feng, Z.; Jiang, J.; Yang, Y.; Zhang, P. Tetrahedron Lett. 2020, 61, 151734. (b) He, X.; Xue, F. Tetrahedron Lett. 2014, 55, 1956.

  21. (a) Flefel, E. M.; Tantawy, W. A.; Abdel-Mageid, R. E.; Amr, Abd El-G. E; Nadeem, R. Res. Chem. Intermed. 2014, 40, 1365. (b) Venkateswarlu, R.; Kamakshi, C.; Subhash, P. V.; Moinuddin, S. G. A.; Rama Sekhara Reddy, D.; Ward, R. S.; Pelter, A.; Gelbrich, T.; Hursthouse, M. B.; Coles, S. J.; Light, M. E. Tetrahedron 2006, 62, 4463.

  22. (a) Baranov, M. S.; Yampolsky, I. V. Tetrahedron Lett. 2013, 54, 628. (b) Smirnov, A. Yu.; Zaitseva, E. R.; Belozerova, O. A.; Alekseyev, R. S.; Baleeva, N. S.; Zagudaylova, M. B.; Mikhaylov, A. A.; Baranov, M. S. J. Org. Chem. 2019, 84, 15417.

  23. Maksimenko, A. S.; Kislyi, V. P.; Chernysheva, N. B.; Strelenko, Y. A.; Zubavichus, Y. V.; Khrustalev, V. N.; Semenova, M. N.; Semenov, V. V. Eur. J. Org. Chem. 2019, 4260.

  24. Maigali, S. S.; Said, M. M.; Abd-El-Maksoud, M. A.; Soliman, F. M. Monatsh. Chem. 2008, 139, 495.

  25. Boulos, L. S.; Abdel-Malek, H. A.; El-Sayed, N. F.; Moharam, M. E. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 697.

  26. Iesce, M. R.; Cermola, F.; Guitto, A. Synlett 1999, 417.

  27. Zimmer, R.; Buchholz, M.; Collas, M.; Angermann, J.; Homann, K.; Reissig, H.-U. Eur. J. Org. Chem. 2010, 4111.

  28. Knight, D. W.; Lewis, P. B. M.; Abdul Malik, K. M.; Mshvidobadze, E. V.; Vasilevsky, S. F. Tetrahedron Lett. 2002, 43, 9187.

  29. Das, S.; Koley, P.; Pramanik, A. Tetrahedron Lett. 2011, 52, 3243.

  30. Shamala, D.; Shivashankar, K. Synth. Commun. 2017, 47, 105.

Download references

This work was supported by the Russian Foundation for Basic Research (grant 18-03-00094).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Alexey V. Nizovtsev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1280–1282

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nizovtsev, A.V., Baranov, M.S. Synthesis of 6H-1,2-oxazin-6-ones (microreview). Chem Heterocycl Comp 56, 1280–1282 (2020). https://doi.org/10.1007/s10593-020-02811-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02811-4

Navigation