The reaction of 3-R-5-amino-1,2,4-triazoles with the ethyl ester of 2-fluoroacetoacetic acid gave 2-R-fluoro[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-ones. The reaction of a 3-R-1,2,4-triazolyl-5-diazonium salt with the ethyl ester of 2-fluoroacetoacetic acid and subsequent cyclization of the triazolylhydrazones lead to 7-R-3-fluoro[1,2,4]triazolo[5,1-c][1,2,4]triazin-4(1H)-ones.
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M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Moscow (2008).
S. A. Giller, R. A. Zhuk, and M. Yu. Lidak, Dokl. Akad. Nauk SSSR, 176, 332 (1967).
N. N. Blokhin (editor), Chemotherapy of Malignant Tumors [in Russian], Meditsina, Moscow (1977), p. 29.R.
A. Andruszkiewicz, H. Chmara, S. Milewski, and E. Borowski, J. Med. Chem., 30, 1715 (1987).
J.-S. Ti, A. S. Steinfeld, F. Naider, A. Gulumoglu, S. V. Lewis, and J. M. Becker, J. Med. Chem., 23, 913 (1980).
H. Kiyokawa, S. Yamada, K. Miyajima, K. Hashimoto, M. Inai, M. Inoue, K. Tatsumi, T. Yamauchi, K. Kurisu, and Y. Chone, US Pat. Appl. 5,420,128 (1995).
J. Kennedy-Smith, Z. K. Sweeney, and J. Wu, WO Pat. Appl. 2008145562 (2008).
H. Shi, J. J. McAtee, S. S. Wirtz, P. Tharnish, A. Juodawlkis, D. C. Liotta, and R. F. Schinazi, J. Med. Chem., 42, 859 (1999).
T. Nitz, K. Salzwedel, C. Finnigan, C. Wild, S. Brunton, S. Flanagan, C. Montlbetti, T. S. Coulter, M. Kimber, F. Magaraci, and D. Johnston, WO Pat. Appl. 2008134035 (2008).
J. Beres, W. G. Bentrude, G. Kruppa, P. A. McKernan, and R. K. Robins, J. Med. Chem., 28, 418 (1985).
J. A. Orvik and D. Shiang, US Pat. Appl.5461153 (1995).
D. L. Pearson, J. J. Tai, and T. J. Adway, US Pat. Appl. 6162915 (2000).
W. R. Carling, S. C. Goodacre, M. G. N. Russel, and L. J. Street, WO Pat. Appl. 2004065388 (2004).
B. Kenda, Y. Quesnel, A. Ates, P. Michel, L. Turet, and J. Mercier, WO Pat. Appl. 2006128692 (2006).
B. Nolte, I. Sucholeiki, T. Feuerstein, B. Gallagher, X. Wu, C. Steeneck, C. Gege, H. Deng, J. van Veldhuisen, and A. Taveras, WO Pat. Appl. 2008063671 (2008).
G. Doria, C. Passarotti, A. Buttinoni, US Pat. Appl. 4537962 (1985).
V. L. Rusinov, E. N. Ulomskii, O. N. Chupakhin, and V. N. Charushin, Izv. Akad. Nauk, Ser. Khim., 967 (2008).
S. L. Deev, M. V. Yasko, I. L. Karpenko, A. N. Korovina, A. L. Khandazhinskaya, V. L. Andronova, G. A. Galegov, E. N. Ulomskii, and M. K. Kukhanova, Bioorg. Chem., 38, 265 (2010).
I. F. Lutsenko (editor), Organic Reactions [Russian translation], Vol. 10, Izd. Inos. Lit., Moscow (1963), p. 148.
E. J. Gray, M. F. G. Stevens, G. Tennant, and R. J. S. Vevers, J. Chem. Soc., Perkin Trans. 1, 1496 (1976).
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*Dedicated to Academician V. N. Charushin on the occasion of his sixtieth birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1411–1417, September, 2011.
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Ulomskiy, E.N., Medvedeva, N.R., Shchepochkin, A.V. et al. Fluorinated [1,2,4]triazolo[1,5-a]pyrimidines and [1,2,4]triazolo[5,1-c][1,2,4]triazines*. Chem Heterocycl Comp 47, 1164–1169 (2011). https://doi.org/10.1007/s10593-011-0887-9
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DOI: https://doi.org/10.1007/s10593-011-0887-9