Abstract
A new method for the phosphorylation of benzo-1,3-azoles (benzoxazole, benzothiazole, and 3-methylindole) with diethyl phosphite by electrocatalytic oxidation was proposed. The process occurs under electrochemical mild conditions (room temperature, normal pressure) in the presence of silver salts or silver oxide. This method allows one to obtain 2-phosphorylated products of benzo-1,3-azoles in good yield (up to 75%).
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D. Kumar, M. R. Jacob, M. B. Reynolds, S. M. Kerwin, Bioorg. Med. Chem., 2002, 10, 3997.
S. M. Rida, F. A. Ashour, S. A. M. El-Hawash, M. M. El-Semary, M. H. Badr, M. A. Shalaby, Eur. J. Med. Chem., 2005, 40,949.
J. S. Kim, Q. Sun, B. Gatto, C. Yu, A. Liu, L. F. Liu, E. J. LaVoie, Bioorg. Med. Chem., 1996, 4,621.
D. W. Dunwell, D. J. Evans, Med. Chem., 1977, 20,797.
N. N. Mel’nikov, K. V. Novozhilov, S. P. Belan, Pestitsidy i regulyatory rosta rastenii [Pesticides and Regulators of Plant Growth], Moscow, Khimiya, 1995, 576 (in Russian).
J. Suzuki, K. Takahashi, S. Fukuda, Pat. US, 2008/058213.
S. Schunk, M. Rich, M. Engels, T. Germann, J. De Vry, R. Jostock, S. Hers, Pat. WO 2010/142402.
R. Storer, C. Dousson, F.-R. Alexandre, A. Roland, Pat. EP 1961757 A1, 2008.
A. I. Razumov, B. G. Liorber, P. A. Gurevich, Zh. Obshch. Khim., 1967, 37, 2782 (in Russian).
A. I. Razumov, P. A. Gurevich, B. G. Liorber, T. D. Borisova, Zh. Obshch. Khim., 1969, 39, 392 (in Russian).
J. Maes, B. U. W. Maes, Adv. Heterocycl. Chem., 2016, 120, 138–188.
Ch. Hou, Y. Ren, R. Lang, X. Hu, Ch. Xia, F. Li, Chem. Commun., 2012, 48, 5181.
H. Wang, X. Li, F. Wu, B. Wan, Synthesis, 2012, 44,941.
C.-B. Xiang, Y.-J. Bian, X.-R. Mao, Z.-Z. Huang, J. Org. Chem., 2012, 77, 7706.
S. H. Kim, K. H. Kim, J. W. Lim, J. N. Kim, Tetrahedron Lett., 2014,531.
Z. Mina, W. Donga, Z. Penga, D. An, Synth. Commun., 2016, 46,128.
W.-B. Sun, J.-F. Xue, G.-Y. Zhang, R.-S. Zeng, L.-T. An, P.-Z. Zhang, J.-P. Zoua, Adv. Synth. Catal., 2016, 358, 1753.
X.-L. Chen, X. Li, L.-B. Qu, Y.-C. Tang, W.-P. Mai, D.-H. Wei, W.-Z. Bi, L.-K. Duan, K. Sun, J.-Y. Chen, D.-D. Ke, Y.-F. Zhao, J. Org. Chem., 2014, 79, 8407.
L. Li, J.-J. Wang, G.-W. Wang, J. Org. Chem., 2016, 81, 5433.
T. V. Gryaznova, Y. B. Dudkina, D. R. Islamov, O. N. Kataeva, O. G. Sinyashin, D. A. Vicic, Yu. H. Budnikova, J. Organomet. Chem., 2015, 785,68.
Yu. B. Dudkina, T. V. Gryaznova, O. N. Kataeva, Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Bull., 2014, 63, 2641.
Yu. H. Budnikova, Sovremennyi organicheskii elektrosintez [Modern Organic Electrosynthesis], Moscow, IFRA-M, 2016, 440 pp. (in Russian).
Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Rev., 2015, 84,917.
S. O. Strekalova, M. N. Khrizanforov, T. V. Gryaznova, V. V. Khrizanforova, Yu. H. Budnikova, Russ. Chem. Bull., 2016, 65, 1295.
M. N. Khrizanforov, S. O. Strekalova, K. V. Kholin, V. V. Khrizanforova, M. K. Kadirov, T. V. Gryaznova, Yu. H. Budnikova, Catal. Today, 2017, 279,133.
Yu. H. Budnikova, T. V. Gryaznova, V. V. Grinenko, Y. B. Dudkina, M. N. Khrizanforov, Pure Appl. Chem., 2017, 89,311.
T. Gryaznova, Yu. Dudkina, M. Khrizanforov, O. Sinyashin, O. Kataeva, Yu. Budnikova, J. Solid State Electrochem., 2015, 19, 2665.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0102—0107, January, 2018
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Yurko, E.O., Gryaznova, T.V., Khrizanforova, V.V. et al. Electrochemical oxidative phosphorylation of azoles in the presence of silver catalysts. Russ Chem Bull 67, 102–107 (2018). https://doi.org/10.1007/s11172-018-2043-5
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DOI: https://doi.org/10.1007/s11172-018-2043-5