Abstract
A convenient method for the synthesis previously unknown hydroxy-containing aryl(hetaryl)-ethenes (terarylenes) with a pyrazole bridge was elaborated, which is based on the reaction of hydrazines with the products of condensation of allomaltol with arylglyoxals. Two isomeric pyrazoles can be formed depending on the nature of substituents in the hydrazine molecule. The protocols for identification of obtained products were suggested based on 2D 1H-13C HMBC NMR spectroscopy and 1D selective NOESY experiments (SELNOGP).
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References
N. Hoffmann, Chem. Rev., 2008, 108, 1052.
A. B. Beeler, Chem. Rev., 2016, 116, 9629.
K. B. Jørgensen, Molecules, 2010, 15, 4334.
V. G. Melekhina, V. S. Mityanov, A. N. Fakhrutdinov, K. A. Lyssenko, V. A. Barachevsky, T. Valova, I. Martynov, A. Ayt, M. M. Krayushkin, J. Photochem. Photobiol. A, 2019, 369, 34.
V. G. Melekhina, V. S. Mityanov, B. V. Lichitsky, A. N. Komogortsev, K. A. Lyssenko, M. M. Krayushkin, Eur. J. Org. Chem., 2019, 6, 1335.
V. G. Melekhina, V. S. Mityanov, B. V. Lichitsky, A. N. Komogortsev, A. N. Fakhrutdinov, E. D. Daeva, M. M. Krayushkin, Tetrahedron Lett., 2019, 60, 1745.
A. N. Komogortsev, B. V. Lichitsky, A. D. Tretyakov, A. N. Fakhrutdinov, A. A. Dudinov, M. M. Krayushkin, J. Heterocycl. Chem., 2019, 56, 3081.
Ch. Rajitha, P. K. Dubey, V. Sunku, F. J. Piedrafita, V. R. Veeramaneni, M. Pal, Eur. J. Med. Chem., 2011, 46, 4887.
V. S. Moskvina, S. V. Shilin, V. P. Khilya, Chem. Heterocycl. Compd., 2015, 51, 799.
A. Aguilar, H. Zhou, L. Chen, L. Liu, L. Bai, D. McEachern, Ch. Yang, J. Meagher, J. Stuckey, Sh. Wang, J. Med. Chem., 2013, 56, 3048.
US Pat. 2004/229900; https://worldwide.espacenet.com.
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This work was financially supported by the Russian Science Foundation (Project No. 18-13-00308).
Based on the Materials of the International Markovnikov Congress on Organic Chemistry (July 21–28, 2019, Moscow-Kazan, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0758–0762, April, 2020.
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Komogortsev, A.N., Melekhina, V.G., Lichitsky, B.V. et al. Synthesis of hydroxy-containing terarylenes with pyrazole and allomaltol fragments. Russ Chem Bull 69, 758–762 (2020). https://doi.org/10.1007/s11172-020-2829-0
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DOI: https://doi.org/10.1007/s11172-020-2829-0