A sequence of alkylation, cyclization, and oxidation reactions was used to convert 5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenylformazans into 6-alkyl-5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenylverdazyls and 5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenyl-6-vinylverdazyls. The paramagnetic and electrochemical properties of the obtained compounds were studied.
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(a) Brook, D. J. R. Comment. Inorg. Chem. 2015, 35, 1. (b) Hicks, R. G. In Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Еd.; John Wiley & Sons: Chichester, 2010, p. 245. (c) Lipunova, G. N.;. Fedorchenko, T. G.; Chupakhin, O. N. Russ. Chem. Rev. 2013, 82, 701. [Usp. Khim. 2013, 82, 701.] (d) Le, T.-N.; Grewal, H.; Changoco, V.; Truong, V.; Brook, D. J. R. Tetrahedron 2016, 72, 6368. (e) Brook, D. J. R.; Yee, G. T. J. Org. Chem. 2006, 71, 4889. (f) Haller, B. C.; Chambers, D.; Cheng, R.; Chemistruck, V.; Hom, T. F.; Li, Z.; Nguyen, J.; Ichimura, A.; Brook, D. J. R. J. Phys. Chem. A 2015, 119, 10750.
(a) Koivisto, B. D.; Hicks, R. G. Coord. Chem. Rev. 2005, 249, 2612. (b) Lemaire, M. T. Pure Appl. Chem. 2004, 76, 277. (c) Johnston, C. W.; McKinnon, S. D. J.; Patrick, B. O.; Hicks, R. G. Dalton Trans. 2013, 42, 16829.
Le, T.-N.; Trevisan, T.; Lieu, E.; Brook, D. J. R. Eur. J. Org. Chem. 2017, 1125.
Petunin, P. V.; Martynko, E. A.; Trusova, M. E.; Kazantsev, M. S.; Rybalova, T. V.; Valiev, R. R.; Uvarov, M. N.; Mostovich, E. A.; Postnikov, P. S. Eur. J. Org. Chem. 2018, 4802.
Matuschek, D.; Eusterwiemann, S.; Stegemann, L.; Doerenkamp, C.; Wibbeling, B.; Daniliuc, C. G.; Doltsinis, N. L.; Strassert, C. A.; Eckert, H.; Studer, A. Chem. Sci. 2015, 6, 4712.
Shchipanov, V. P.; Nagovskaya, S. A.; Podenko, L. S. Chem. Heterocycl. Compd. 1977, 13, 213. [Khim. Geterotsikl. Soedin. 1977, 266.]
Fedorchenko, T. G.; Lipunova, G. N.; Shchepochkin, A. V.; Tsmokalyuk, A. N.; Slepukhin, P. A.; Chupakhin, O. N. Mendeleev Commun. 2018, 28, 297.
(a) Olkhovikova, N. B.; Rusinova, L. I.; Shmelev, L. V.; Lipunova, G. N.; Klyuev, N. A.; Yeltsov, A. V. Zh. Obshch. Khim. 1988, 58, 1626. (b) Klyuev, N. A.; Zhilnikov, V. G.; Aleksandrov, G. G.; Grandberg, I. I.; Lipunova, G. N. Zh. Org. Khim. 1983, 19, 2615.
Polumbrik, O. M. Chemistry of Verdazyl Radicals [in Russian]; Naukova Dumka: Kiev, 1984.
Podenko, L. S.; Chirkov, A. K.; Shchipanov, V. P. Zh. Struktur. Khim. 1980, 21, 187.
Gilroy, J. B.; McKinnon, S. D. J.; Koivisto, B. D.; Hicks, R. G. Org. Lett. 2007, 9, 4837.
Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367.
Stoll, S.; Schweiger, A. J. Magn. Reson. 2006, 178, 42.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.
This work was performed within the framework of State Assignment АААА-А19-119012290117-6 and received financial support from the Program of Ural Branch of the Russian Academy of Sciences (project 18-3-3-16), while using equipment at the Collective Use Center “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(6), 560–565
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Fedorchenko, T.G., Lipunova, G.N., Shchepochkin, A.V. et al. Synthesis, spectral and electrochemical properties of halogenated 6-alkyl-5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenylverdazyls and 5-aryl-1-(benzo[d]thiazol-2-yl)-3-phenyl-6-vinylverdazyls. Chem Heterocycl Comp 55, 560–565 (2019). https://doi.org/10.1007/s10593-019-02496-4
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DOI: https://doi.org/10.1007/s10593-019-02496-4