Although first synthesis of 1,2,4-benzotriazine was performed at the end of 19th century still new methods for their preparation are developed. This microreview combines recent (2006–2017) information on the strategies used for the synthesis of 1,2,4-benzotriazines – [4+2] cycloaddition reactions, diverse cyclocondensations, heterocyclization of N-(2-aminoaryl)hydrazides, etc.
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(a) Hay, M. P.; Hicks, K. O.; Pchalek, K.; Lee, H. H.; Blaser, A.; Prujin, F. B.; Anderson, R. F.; Shinde, S. S.; Wilson, W. R.; Denny, W. A. J. Med. Chem. 2008, 51, 6853. (b) Boyle, R. G.; Travers, S. WO Patent 2008015429. (c) Zeller, M. WO Patent 9838161.
Constantinides, C. P.; Obijalska, E.; Kaszyński, P. Org. Lett. 2016, 18, 916.
(a) Jasiński, M.; Szczytko, J.; Pociecha, D.; Monobe, H.; Kaszyński, P. J. Am. Chem. Soc. 2016, 168, 9421. (b) Kaszyński, P.; Constantinides, C. P.; Young, V. G. Angew. Chem., Int. Ed. 2016, 55, 1.
Bischler, A. Chem. Ber. 1889 , 22, 280.
Guo, H.; Liu, J.; Wang, X.; Huang, G. Synlett 2012, 903.
Zhou, Y.; Zhang, Z.; Jiang, Y.; Pan, X.; Ma, D. Synlett 2015, 26, 1586.
(a) Noronha, G.; Barrett, K.; Cao, J.; Dneprovskaia, E.; Fine, R.; Gong, X.; Gritzen, C.; Hood, J.; Kang, X.; Klebansky, B.; Li, G.; Liao, W.; Lohse, D.; Mak, C. C.; McPherson, A.; Palanki, M. S. S.; Pathak, V. P.; Renick, J.; Soll, R.; Splittgrber, U.; Wrasidlo, W.; Zheng, B.; Zhao, N.; Zhou, Y. Bioorg. Med. Chem. Lett. 2006, 16, 5546. (b) Noronha, G.; Barett, K.; Boccia, A.; Brodhag, T.; Cao, J.; Chow, C. P.; Dneprovskaia, E.; Doukas, J.; Fine, R.; Gong, X.; Gritzen, C.; Gu, H.; Hanna, E.; Hood, J. D.; Hu, S.; Kang, X.; Key, J.; Klebansky, B.; Kousba, A.; Li, G.; Lohse, D.; Mak, C. C.; McPherson, A.; Palanki, M. S. S.; Pathak, V. P.; Renick, J.; Shi, F.; Soll, R.; Splittgrber, U.; Stoughton, S.; Tang, S.; Yee, S.; Zeng, B.; Zhao, N.; Zhu, H. Bioorg. Med. Chem. Lett. 2007, 17, 602. (c) Cao, J.; Fine, R.; Gritzen, C.; Hood, J. Kang, X., Klebansky, B.; Lohse, D.; Mak, C. C.; McPherson, A.; Noronha, G.; Palanki, M. S. S.; Pathak, V. P.; Renick, J.; Soll, R.; Zeng,B.; Zhu, H. Bioorg. Med. Chem. Lett. 2007, 17, 5812. (d) Boyd, M.; Hay, M. P.; Boyd, P. D. W. Magn. Reson. Chem. 2006, 44, 948.
Kotovskaya, S. K.; Zhumbaeva, G. A.; Perova, N. M.; Baskakova, Z. M.; Charushin, V. N.; Chupakhin, O. N.; Belanov, E. F.; Bormotov, N. I.; Balakhnin, S. M.; Serova, O. A. Pharm. Chem. J. 2007, 41, 62.
Guirado, A.; López Sánchez, J. I.; Moreno, R.; Gálvez, J. Tetrahedron Lett. 2013, 54, 1542.
Alajarin, M; Bonillo, B.; Marin-Luna, M.; Vidal, A.; Orenes, R.-A. J. Org. Chem. 2009, 74, 3558. (b) Alajarin, M; Bonillo, B.; Marin-Luna, M.; Sanchez-Andrad, P.; Vidal, A. Eur. J. Org. Chem. 2010, 694.
(a) Zhong, Z.; Hong, R.; Wang, X. Tetrahedron Lett. 2010, 51, 6763. (b) Yin, R.; Zhou, L.; Liu, H.; Mao, H.; Lü, X.; Wang, X. Chin. J. Chem. 2013, 31, 143.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 846–848
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Obijalska, E., Kowalski, M.K. Recent progress in the synthesis of 1,2,4-benzotriazines (microreview). Chem Heterocycl Comp 53, 846–848 (2017). https://doi.org/10.1007/s10593-017-2134-5
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DOI: https://doi.org/10.1007/s10593-017-2134-5