6-Alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-4H-chromen-4-ones recyclized into 6-alkyl-4-[5-dialkylaminomethyl-4-(4-methyl-1,3-thiazol-2-yl)-1H-pyrazol-3-yl]-1,3-benzenediols under the influence of hydrazine hydrate.
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T. V. Shokol, V. A. Turov, V. V. Semenyuchenko, N. V. Krivokhizha, and V. P. Khilya, Khim. Geterotsikl. Soedin., 571 (2006). [Chem. Heterocycl. Compd., 42, 500 (2006).]
S. L. Bogza, V. I. Dulenko, S. Yu. Zinchenko, K. I. Kobrakov, and I. V. Pavlov, Khim. Geterotsikl. Soedin., 1737 (2004). [Chem. Heterocycl. Compd., 40, 1506 (2004).]
Yu. M. Volovenko, T. A. Volovnenko, and A. V. Stel’makh, in: Abstr. XXI Ukrain. Konf. Org.. Khim., [in Ukrainian], Chernigiv (2007), p. 144.
N. V. Gorbulenko, T. V. Shokol, V. P. Khilya, and V. M. Kovalyov, in: Abstr. III Mizhnar. Nauk. prakt. Conf. "Current Problems of Biology, Ecology, and Chemistry" [in Ukrainian], Zaporizhzhya (2012), p. 308.
T. I. El-Emary and E. A. Banhite, Pharmazie, 54, 106 (1999); Chem. Abstr., 130, 232289 (1999).
T.-L. Liu, S.-L. Yu, and A.-M. Yu, Gaodeng Xuexiao Huaxue Xuebao, 19, 232 (1998); Chem. Abstr., 128, 192588 (1998).
Z.-N. Huang and Z.-M. Li, Gaodeng Xuexiao Huaxue Xuebao, 16, 1888 (1995); Chem. Abstr., 124, 317062 (1996).
H. Obara, T. Igarashi, K. Sakurai, and T. Oshii, JP Pat. Appl. 10306077
O. Bruno, A. Ranise, F. Bondavalli, P. Schenone, M. D’Amico, A. Filippelli, W. Filippelli, and F. Rossi, Farmaco, 48, 949 (1993).
K.-M. J. Cheung, T. P. Matthews, K. James, M. G. Rowlands, K. J. Boxall, S. Y. Sharp, A. Maloney, S. M. Roe, C. Prodromou, L. H. Pearl, G. W. Aherne, E. McDonald, and P. Workman, Bioorg. Med. Chem. Lett., 15, 3338 (2005).
A. Kreusch, S. Han, A. Brinker, V. Zhou, H.-S. Choi, Y. He, S. A. Lesley, J. Caldwell, and H.-J. Gu, Bioorg. Med. Chem. Lett., 15, 1475 (2005).
V. P. Khilya, I. P. Kupchevskaya, and L. G. Grishko, in: Chemistry and Biological Activity of Synthetic and Natural Compounds. Nitrogen Heterocycles and Alkaloids [In Russian], Vol. 1, Iridium Press, Moscow (2001), p. 147.
B. W. Dymock, X. Barril, P. A. Brough, J. E. Cansfield, A. Massey, E. McDonald, R. E. Hubbard, A. 4212 (2005).
M.-C. Sacquet, M-.C. Fargeau-Bellassoued, and B. Graffe, J. Heterocycl. Chem., 28, 667 (1991).
T. V. Shokol, N. V. Gorbulenko, A. V. Turov, and V. P. Khilya, Khim. Geterotsikl. Soedin., 1266 (2012). [Chem. Heterocycl. Compd., 48, 1181 (2012).]
T. V. Shokol, N. V. Gorbulenko, and V. P. Khilya, Khim. Geterotsikl. Soedin., 1568 (2011). [Chem. Heterocycl. Compd., 47, 1298 (2011).]
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, 351-356, February 2013.
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Shokol, T.V., Gorbulenko, N.V., Turov, A.V. et al. Synthesis of 6-alkyl-4-[5-dialkylaminomethyl-4-(4-methyl-1,3-thiazol-2-yl)-1H-pyrazol-3-yl]-1,3-benzenediols. Chem Heterocycl Comp 49, 325–330 (2013). https://doi.org/10.1007/s10593-013-1250-0
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DOI: https://doi.org/10.1007/s10593-013-1250-0