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.
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(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.
Stevenson, T. M. US Patent 20120329787A1.
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.
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.
Rios, M. Y.; Navarro, V.; Ramírez-Cisneros, M. Á.; Salazar-Rios, E. J. Nat. Prod. 2017, 80, 3112.
Csende, F.; Stájer, G. Heterocycles 2000, 53, 1379.
(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.
Yuossef, M. S. K.; Fahmy, A. F.; Halim, M. S. A.; Hassan, M. A.; Sauer, J. Org. Prep. Proced. Int. 2005, 37, 247.
(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.]
Bildirici, I.; Şener, A.; Tozlu, I. Med. Chem. Res. 2007, 16, 418.
Sakthidharan, C. P.; Sampathkumar, N. Heterocycl. Lett. 2011, 1, 43.
Faidallah, H. M.; Khan, K. A.; Makki, M. S. I. J. Chin. Chem. Soc. 2011, 58, 191.
Zhang, Y.; Wang, Q.; Yu, H.; Huang, Y. Org. Biomol. Chem. 2014, 12, 8844.
(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.
Xu, Y.; Hu, W.; Tang, X.; Zhao, J.; Wu, W.; Jiang, H. Chem. Commun. 2015, 51, 6843.
Suchand, B.; Satyanarayana, G. Eur. J. Org. Chem. 2018, 2233.
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.
Dang, T. T.; Albrecht, U.; Langer, P. Synthesis 2006, 2515.
Pathak, S.; Debnath, K.; Hossain, Sk. T.; Mukherjee, S. K.; Pramanik, A. Tetrahedron Lett. 2013, 54, 3137.
(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.
(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.
(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.
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.
Maigali, S. S.; Said, M. M.; Abd-El-Maksoud, M. A.; Soliman, F. M. Monatsh. Chem. 2008, 139, 495.
Boulos, L. S.; Abdel-Malek, H. A.; El-Sayed, N. F.; Moharam, M. E. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 697.
Iesce, M. R.; Cermola, F.; Guitto, A. Synlett 1999, 417.
Zimmer, R.; Buchholz, M.; Collas, M.; Angermann, J.; Homann, K.; Reissig, H.-U. Eur. J. Org. Chem. 2010, 4111.
Knight, D. W.; Lewis, P. B. M.; Abdul Malik, K. M.; Mshvidobadze, E. V.; Vasilevsky, S. F. Tetrahedron Lett. 2002, 43, 9187.
Das, S.; Koley, P.; Pramanik, A. Tetrahedron Lett. 2011, 52, 3243.
Shamala, D.; Shivashankar, K. Synth. Commun. 2017, 47, 105.
This work was supported by the Russian Foundation for Basic Research (grant 18-03-00094).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1280–1282
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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
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DOI: https://doi.org/10.1007/s10593-020-02811-4