Abstract
The reaction of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with alcohols and sodium alkoxides was evaluated under various conditions. Depending on the reaction conditions, either alkoxy or hydroxy derivatives of [1,2,5]thiadiazolo[3,4-d]pyridazine can be obtained. 4,7-Di-(dodecyloxy)- and 4,7-di(hexyloxy)[1,2,5]thiadiazolo[3,4-d]pyridazines, which may be of interest as the compounds exhibiting liquid crystalline properties, were synthesized for the first time.
Similar content being viewed by others
References
S. Chaurasia, J. T. Lin, Chem. Rec., 2016, 16, 1311.
E. A. Knyazeva, O. A. Rakitin, Russ. Chem. Rev., 2016, 85, 1146.
X. Zhang, M. Grätzel, J. Hua, Front. Optoelectron., 2016, 9, 3.
K. Takimiya, I. Osaka, M. Nakano, Chem. Mater., 2014, 26, 587.
Y. Wu, W. Zhu, Chem. Soc. Rev., 2013, 42, 2039.
A. Blaszczyk, Dyes Pigm., 2018, 149, 707.
E. A. Knyazeva, W. Wu, T. N. Chmovzh, N. Robertson, J. D. Woollins, O. A. Rakitin, Sol. Energy, 2017, 144, 134.
T. N. Chmovzh, E. A. Knyazeva, E. Tanaka, V. V. Popov, L. V. Mikhalchenko, N. Robertson, O. A. Rakitin, Molecules, 2019, 24, 1588.
M. S. Mikhailov, N. S. Gudim, E. A. Knyazeva, E. Tanaka, L. Zhang, L. V. Mikhalchenko, N. Robertson, O. A. Rakitin, J. Photochem. Photobiol. A, 2020, 391, 112333.
A. V. Akkuratov, P. A. Troshin, Polym. Sci., Ser. B (Engl. Transl.), 2014, 56, 414.
G. V. Bulavko, A. A. Ishchenko, Russ. Chem. Rev., 2014, 83, 575.
Y. Zhao, Y. Guo, Y. Liu, Adv. Mater., 2013, 25, 5372.
X. Guo, A. Facchetti, T. J. Marks, Chem. Rev., 2014, 114, 8943.
A. Leventis, T. N. Chmovzh, E. A. Knyazeva, Y. Han, M. J. Heeney, O. A. Rakitin, H. Bronstein, Polym. Chem., 2020, 11, 581.
Y. Zhang, J. Zou, C.-C. Cheuh, H.-L. Yip, A. K.-Y. Jen, Macromolecules, 2012, 45, 5427.
A. C. Stuart, J. R. Tumbleston, H. Zhou, W. Li, S. Liu, H. Ade, W. You, J. Am. Chem. Soc., 2013, 135, 1806.
J. Roncali, Macromol. Rapid Commun., 2007, 28, 1761.
M. Velusamy, K. R. J. Thomas, J. T. Lin, Y. C. Hsu, K. C. Ho, Org. Lett., 2005, 7, 1899.
Y. Cui, Y. Z. Wu, X. F. Lu, X. Zhang, G. Zhou, F. B. Miapeh, W. H. Zhu, Z. S. Wang, Chem. Mater., 2011, 23, 4394.
H. Jiang, Y. Wu, A. Islam, M. Wu, W. Zhang, C. Shen, H. Zhang, E. Li, H. Tian, W.-H. Zhu, ACS Appl. Mater. Inter., 2018, 10, 13635.
S. Y. Qu, W. J. Wu, J. L. Hua, C. Y. Kong, T. Long, H. Tian, J. Phys. Chem. C, 2010, 114, 1343.
J. Liu, K. Wang, F. Xu, Z. Tang, W. Zheng, J. Zhang, C. Li, T. Yu, X. You, Tetrahedron Lett., 2011, 52, 6492.
T. N. Chmovzh, E. A. Knyazeva, L. V. Mikhalchenko, I. S. Golovanov, S. A. Amelichev, O. A. Rakitin, Eur. J. Org. Chem., 2018, 41, 5668.
T. N. Chmovzh, E. A. Knyazeva, K. A. Lyssenko, V. V. Popov, O. A. Rakitin, Molecules, 2018, 23, 2576.
C. Subramanyam, A. J. Duplantier, M. A. Dombroski, S. P. Chang, C. A. Gabel, C. Whitney-Pickett, M. Fisher, Bioorg. Med. Chem. Lett., 2011, 21, 5475.
Author information
Authors and Affiliations
Corresponding author
Additional information
This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-33-00106 mol_a).
T. N. Chmovzh is grateful to the South Ural State University for the financial support.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2167—2170, November, 2020.
Rights and permissions
About this article
Cite this article
Chmovzh, T.N., Knyazeva, E.A., Krukovskaya, N.V. et al. Reactions of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with alcohols. Russ Chem Bull 69, 2167–2170 (2020). https://doi.org/10.1007/s11172-020-3017-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-020-3017-y