The review presents the general methods for the formation of the framework of 1,4-dihydro- 1,2,4-benzotriazin-4-yl radicals (Blatter radicals) and their polycyclic derivatives published over the past 7 years. The target heterocyclic structures are formed by a number of approaches such as oxidative cyclization of amidrazones, addition of organolithium reagents to 1,2,4-benzotriazines, intramolecular cyclizations of 1,2,4-benzotriazine derivatives, and other methods.
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Ji, Y.; Long, L.; Zheng, Y. Mater. Chem. Front. 2020, 4, 3433.
(a) Rogers, F. J. M.; Norcott, P. L.; Coote, M. L. Org. Biomol. Chem. 2020, 18, 8255. (b) Ziarani, G. M.; Mostofi, M.; Gholamzadeh, P.; Mohammadi-Khanaposhtani, M.; Yavari, H. ARKIVOC 2019, (i), 41.
Sidharth, T. N. S.; Nasani, R.; Gupta, A.; Sooraj, B. N. S.; Roy, S.; Mondal, A.; Konar, S. Inorg. Chim. Acta 2020, 503, 119395.
Kapuściński, S.; Szczytko, J.; Pociecha, D.; Jasiński, M.; Kaszyński, P. Mater. Chem. Front. 2021, 5, 6512.
Poryvaev, A. S.; Gjuzi, E.; Polyukhov, D. M.; Hoffmann, F.; Fröba, M.; Fedin, M. V. Angew. Chem., Int. Ed. 2021, 60, 8683.
Kapuściński, S.; Anand, B.; Bartos, P.; Garcia Fernandez, J. M.; Kaszyński, P. Molecules 2022, 27, 1176.
Areephong, J.; Mattson, K. M.; Treat, N. J.; Poelma, S. O.; Kramer, J. W.; Sprafke, H. A.; Latimer, A. A.; de Alaniz, J. R.; Hawker, C. J. Polym. Chem. 2016, 7, 370.
Zhang, Y.; Zheng, Y.; Zhou, H.; Miao, M.-S.; Wudl, F.; Nguyen, T.-Q. Adv. Mater. 2015, 27, 7412.
Calzolari, A.; Rajca, A.; Casu, M. B. J. Mater. Chem. C 2021, 9, 10787.
(a) Kaszyński, P.; Kapuściński, S.; Ciastek-Iskrzycka, S. Adv. Heterocycl. Chem. 2019, 128, 263. (b) Jasiński, M.; Szczytko, J.; Pociecha, D.; Monobe, H.; Kaszyński, P. J. Am. Chem. Soc. 2016, 138, 9421.
Shu, C.; Pink, M.; Junghoefer, T.; Nadler, E.; Rajca, S.; Casu, M. B.; Rajca, A. J. Am. Chem. Soc. 2021, 143, 5508.
Bodzioch, A.; Zheng, M.; Kaszynski, P.; Utecht, G. J. Org. Chem. 2014, 79, 7294.
Ciccullo, F.; Gallagher, N. M.; Geladari, O.; Chassé, T.; Rajca, A.; Casu, M. B. ACS Appl. Mater. Interfaces 2016, 8, 1805.
Pomiklo, D.; Bodzioch, A.; Pietrzak, A.; Kaszyński, P. Org. Lett. 2019, 21, 6995.
Constantinides, C. P.; Obijalska, E.; Kaszyński, P. Org. Lett. 2016, 18, 916.
Bazzi, F.; Danke, A. J.; Lawson, D. B.; Manoli, M.; Leitus, G. M.; Koutentis, P. A.; Constantinides, C. P. CrystEngComm 2020, 22, 4306.
Bodzioch, A.; Pietrzak, A.; Kaszyński, P. Org. Lett. 2021, 23, 7508.
Kaszyński, P.; Constantinides, C. P.; Young, V. G., Jr. Angew. Chem., Int. Ed. 2016, 55, 11149.
Bartos, P.; Anand, B.; Pietrzak, A.; Kaszyński, P. Org. Lett. 2020, 22, 180.
Bartos, P.; Young, V. G., Jr.; Kaszyński, P. Org. Lett. 2020, 22, 3835.
Bartos, P.; Celeda, M.; Pietrzak, A.; Kaszyński, P. Org. Chem. Front. 2022, 9, 929.
Grant, J. A.; Lu, Z.; Tucker, D. E.; Hockin, B. M.; Yufit, D. S.; Fox, M. A.; Kataky, R.; Chechik, V.; O'Donoghue, A. C. Nat. Commun. 2017, 8, 15088.
Paul, A.; Nasani, R.; Mondal, A.; Roy, S.; Vela, S.; Konar, S. Cryst. Growth Des. 2020, 20, 6296.
Savva, A. C.; Mirallai, S. I.; Zissimou, G. A.; Berezin, A. A.; Demetriades, M.; Kourtellaris, A.; Constantinides, C. P.; Nicolaides, C.; Trypiniotis, T.; Koutentis, P. A. J. Org. Chem. 2017, 82, 7564.
Takahashi, Y.; Miura, Y.; Yoshioka, N. New J. Chem. 2015, 39, 4783.
Berezin, A. A.; Zissimou, G.; Constantinides, C. P.; Beldjoudi, Y.; Rawson, J. M.; Koutentis, P. A. J. Org. Chem. 2014, 79, 314.
Zissimou, G. A.; Berezin, A. A.; Manoli, M.; Nicolaides, C.; Trypiniotis, T.; Koutentis, P. A. Tetrahedron 2020, 76, 131077.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 196–198
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Fershtat, L.L. Synthesis of 1,4-dihydro-1,2,4-benzotriazin-4-yl radicals (microreview). Chem Heterocycl Comp 58, 196–198 (2022). https://doi.org/10.1007/s10593-022-03072-z
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DOI: https://doi.org/10.1007/s10593-022-03072-z